Personalized care for your dog or cat - Winslow

Highly-rated overnight sitters - Winslow

Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

1 / 1
Sitter Profile Image: Christine N.
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Christine N.
Star Sitter
from
$41
per night
5.0 out of 5 stars
131 reviews
63 repeat clients
35 years of experience
Prairie Hills, Monticello, WI, 53570

Once again Joey's stay with Christine was a great success. Christine has a ton of dog experience and it shows, she handles Joey effortlessly and helps her to adjust to staying with other dogs. We will definitely book again in the future!

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Paula D.
Sitter Profile Image: Dan W.
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Dan W.
Star Sitter
from
$25
per night
4.9 out of 5 stars
76 reviews
28 repeat clients
15 years of experience
Mineral Point, WI, 53565

Boomer had a great time with Dan! We appreciate that he took the time to do a meet and greet beforehand and showed us around the space. When we picked Boomer up, it was clear he had a good time and really tuckered out! Thanks again Dan.

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Matt & Kendra S.
Sitter Profile Image: Mary S.
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Mary S.
Star Sitter
from
$30
per night
5.0 out of 5 stars
93 reviews
38 repeat clients
20 years of experience
Lake Summerset, IL, 61019

Mary and her husband are absolutely wonderful caregivers! I received daily updates about my Ivy and they were very sweet, loving and caring with her. I highly recommend Mary to anyone who needs to be able to trust 100% that their fur babies will be well cared for!

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Angela F.
Sitter Profile Image: Jilly W.
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Jilly W.
from
$37
per night
5.0 out of 5 stars
30 reviews
11 repeat clients
43 years of experience
Freeport, IL, 61032

Jilly was great! We appreciated her quick response to our request. Charlie seemed to really enjoy his stay at the farm. Jilly also shared updates and photos with us which was really nice.

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Rose M.
Sitter Profile Image: Kate S.
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Kate S.
from
$75
per night
5.0 out of 5 stars
24 reviews
10 repeat clients
32 years of experience
Belleville, WI, 53508

Teddy had a great stay with Kate! We loved getting photo updates, and it was such a thoughtful touch that she sent him home with his favorite toy (Patrick Star!) and a goodie bag. We’ll definitely be reaching out to Kate again in the future.

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Kiersten B.
Sitter Profile Image: Lisa N.
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Lisa N.
from
$74
per night
5.0 out of 5 stars
52 reviews
12 repeat clients
20 years of experience
Freeport, IL, 61032

Lisa and her family watched our standard poodle for a weekend and did a fantastic job. She posted regular updates (with photos) and treated our pup as one of her own.

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Arzhange S.
Sitter Profile Image: Sue K.
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Sue K.
from
$25
per night
30 years of experience
Orangeville, IL, 61060

About: ✨ Services I Offer 🐶 In‑Home Pet Care (At our welcoming home on 4 peaceful acres) Your pets don’t just stay with us—they vacation with us! • Daily walks, outdoor adventures, and plenty of fresh air • Cozy relaxation, cuddles, and companionship throughout the day • A clean, safe, loving environment that feels just like home—only better • Perfect for pets who thrive with extra attention and room to roam 🏡 House Sitting for Your Pets Bringing comfort and consistency right to your doorstep. • No job too big or too small—every pet gets VIP treatment • Keep your peace of mind while you’re away • I follow your pet’s routines so they stay relaxed, happy, and stress‑free • Reliable, attentive care from someone who treats your pets like family --- ❤️ Over 30 Years of Experience A lifetime of caring for dogs and cats means your pets are in loving, knowledgeable, trustworthy hands. I am independently insured as a professional pet sitter. Rover bookings are also backed by Rover’s pet‑care guarantee. Find us on FB Old Soul Pet Sitting I work from home, which means your fur babies get all‑day attention, love, and care—no long stretches alone, ever. Whether your pet is an adventurer or a casual stroller, I’ve got them covered! I walk 3–5 miles a day, so if your pup loves exploring, they’ll be right at home with me. Prefer something calmer? We also have 4 peaceful acres perfect for relaxed sniff‑sessions and easygoing walks. Trust me—there’s LOTS to sniff! Inside, your pet will enjoy premium lounging, too. I’ve set up a couch right in front of our big living‑room window so they can keep tabs on all the outdoor action. Plus, the family room and dining room both have patio doors—meaning plenty of prime viewing spots for curious noses and watchful eyes. Your pet’s comfort, happiness, and enrichment come first—and they’ll feel that from the moment they walk in the door. ❤️ Pets Are Family—And That’s Exactly How I Treat Them In my home, pets aren’t “just animals”—they’re family. Our own dogs and cats have always slept in our bed, curled up on the couch, and enjoyed every creature comfort right alongside us. I’ve had pets of all sizes throughout my life, and I truly love them all. I know how hard it can be to enjoy time away when you’re worried about your fur babies. That’s why, with me, your pets become my top priority from the moment they arrive. They’ll never be stuck in cages—just freedom, affection, and the good life they deserve! 📸 Daily Updates—Your Way Want a couple of check‑ins or all‑day photo updates? Just tell me your preference, and I’ll exceed your expectations. As a lifelong pet parent myself, I understand how important it is to know your babies are safe, happy, and having fun. 🐾 Trusted Experience You Can Count On I proudly partner with FetchWI and the Green County Humane Society, providing foster care for dogs waiting for their forever homes. Caring, patience, and compassion are at the heart of everything I do. I am independently insured as a professional pet sitter. Rover bookings are also backed by Rover’s pet‑care guarantee.

Sitter Profile Image: Stefanie J.
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Stefanie J.
from
$50
per night
4.6 out of 5 stars
9 reviews
4 repeat clients
10 years of experience
Freeport, IL, 61032

Stefanie was great with Luna. Sent pictures and kept me updated! I felt at ease knowing Luna was being loved in a pet friendly home while I was away. Thank you!

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Amy K.
Sitter Profile Image: Madison S.
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Madison S.
from
$80
per night
4.9 out of 5 stars
11 reviews
4 repeat clients
18 years of experience
Freeport, IL, 61032

Madison did such a great job with Cooper! His excitement, new environment jitters and eating too fast caused him to vomit the first couple of days. Madison handled it like a pro, she seeked guidance from the vet who confirmed what seemed to be happening. She adjusted his food intake to help him keep food down and made some other changes which fixed the problem! Goose, their dog, was a wonderful big brother to Cooper and they all gave him love like he was their own. Cooper was taken on lovely walks on trails and to the dog park and Goose also shared his antlers with Coop which is now his favorite thing to chew! We were very happy with the care given to our crazy little kid and Madison went over and beyond!

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Kirsten B.
Sitter Profile Image: Isabella F.
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Isabella F.
from
$55
per night
8 years of experience
Monroe, WI, 53566

About: Hi, I’m Izzy! I’ve been a professional dog trainer for nearly 4 years, with 8 years of animal care, and am KPA-CCT certified, an AKC evaluator, and experienced with both pet and working dogs. I offer pet sitting and boarding that blends comfort with structure. Your dog will get personalized care, enrichment, and positive experiences while you’re away. Whether you have a high energy puppy or a dog in training, I ensure they stay safe, happy, and well mannered. I currently make my own schedule, with the exception of Fridays, where I’m busy from 1pm-6pm. I love to hike and jog trails, so I typically take my pets with. I also have a pond where we swim in the summer. Safety is always my top priority. I maintain a secure, dog-friendly environment where every pet is supervised and set up for success. I manage introductions carefully, use gates and crates when needed, and never leave dogs unattended together. My home is fully fenced, and I monitor play to ensure everyone stays happy and stress-free. I also follow each owner’s feeding, medication, and training routines closely to keep things consistent and safe.

Sitter Profile Image: Ashley & Timothy L.
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Ashley & Timothy L.
from
$30
per night
20 years of experience
Rock City, IL, 61070

About: We have had a dog or dogs for over 20 years. My husband and I both grew up with dogs as well. Our two dogs have been with us since they were puppies and both of them attended three levels of dog training classes. I work part-time very early in the morning and we spend a lot of time at home because my kids are homeschooled. There is usually always someone at home. I will do as much as I can to accommodate the dog owner’s preference in care for their dog. We have two dogs that can play with your dog. If your dog needs to be in a crate I can accommodate that. Our dogs are not allowed on the couches and chairs but my children do let them sleep in their beds.

Sitter Profile Image: April S.
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April S.
from
$40
per night
5.0 out of 5 stars
3 reviews
15 years of experience
Belleville, WI, 53575

For a newbie on Rover she definitely delivered and did an excellent job! She has enough help around the house to make sure dogs are taken care of and getting attention at all times. She kept me updated as much as I would hope for and I felt the dogs were in good care while I was gone for the week! Would book again next year:)

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Andrew F.
Sitter Profile Image: Ellen W.
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Ellen W.
from
$55
per night
5.0 out of 5 stars
14 reviews
2 repeat clients
12 years of experience
New Glarus, WI, 53574

About: I’ve been pet sitting for friends and family since before I could drive. You name it; dogs, cats, rabbits, chinchillas - I’ve watched them. So if you have other animals that need care, the more the merrier! I love dogs and will be as excited to give your dog a walk as they are! I can give references phone numbers upon request. I have helped train dogs and puppies throughout the years. I may even be able to teach your dog a new trick 😉 I have great patience and a calm, easy-going nature. My husband and myself have opened our home with a very large fenced in backyard to welcome your dogs. Between the two of us, your dogs will feel right at home. My husband is also certified in dog massages (yes it’s a thing! 😅) so if you have a pup with joint or mobility issues, he can assist with that as a bonus! If you are welcoming me into your home, I will be sure it looks just as good as when you left it in my care. Please send me a request to chat about your furry family member - I look forward to meeting you! I currently work part-time and my husband also has a flexible schedule to ensure your dogs have the attention they need during their stay with us. We have a comfortable environment with a large fenced in backyard for your dog to play in and have frequent potty breaks. If your dog needs their own space, we have extra rooms in the house that can be their own during their stay.

Sitter Profile Image: Cassidy H.
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Cassidy H.
from
$35
per night
15 years of experience
German Valley, IL, 61039

About: I have taken care of dogs since I was able to drive myself. My neighbors, family members & friends have trusted me to care for their pets for years. I absolutely love dogs & would love to be able to help you keep them safe & happy in the home. I work 40 hours per week and my schedule changes weekly. So my pets get most of the attention after work or before. Check availability! My schedule is weird, but works because i have days off during the week. I have two dogs currently. I love caring for them & enjoy spending time with them after working, I would love to add a few more to the list.

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Over 4.1 million
dogs curled up for a sleepover in a sitter's home on Rover1

Cat caregivers near you - Winslow

Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

1 / 1
Sitter Profile Image: Sydney M.
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Sydney M.
from
$18
per visit
5.0 out of 5 stars
85 reviews
22 repeat clients
15 years of experience
Monroe, WI, 53566

Sydney has been providing drop-in visits for my cat, lucy for a few years and I’m extremely happy with the service she provides. She is an excellent pet care provider and is also willing to do a few extra tasks such as bringing in the mail and watering plants.

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Jackie R.
Sitter Profile Image: Lileah C.
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Lileah C.
from
$18
per visit
5.0 out of 5 stars
2 reviews
15 years of experience
Freeport, IL, 61032

About: I’ve owned and cared for cats since I was 5 years old and have over 15 years of hands-on experience. I understand that every cat has a unique personality and comfort level. I’m experienced with feeding schedules, litter box cleaning, playtime, brushing, and giving medications if needed. I’m patient with shy cats and attentive to changes in behavior to ensure they feel safe and comfortable while you’re away.

Sitter Profile Image: Madison S.
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Madison S.
from
$25
per visit
4.9 out of 5 stars
11 reviews
4 repeat clients
7 years of experience
Freeport, IL, 61032

I was gone for a week for a family reunion/vacation out of state. It was super hot, so I was worried about my Halley. Came home to a friendly, energetic, and well-hydrated cat. Apparently, Halley also requested lots of head rubs, so she warmed up to Madison pretty well. So happy I found someone I can trust with my fur baby.

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Lisa E.
Sitter Profile Image: Whitney W.
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Whitney W.
from
$45
per visit
5.0 out of 5 stars
5 reviews
13 years of experience
Monroe, WI, 53566

About: As a proud cat parent to two spoiled felines, a curious Bengal and a chatty Oriental Shorthair, I know just how unique and particular cats can be. Whether your kitty is playful and energetic or prefers quiet companionship, I’m here to provide the personalized care they need while you’re away. From feeding and litter box maintenance to playtime, brushing, and cuddles (if they’re into that!), I’ll treat your cat like one of my own. I understand cat body language, respect their space, and know how to earn their trust, on their terms, of course!

Sitter Profile Image: Mia H.
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Mia H.
from
$20
per visit
5.0 out of 5 stars
2 reviews
4 years of experience
Argyle, WI, 53504

About: I have had a passion for dogs since I’ve been 11. I have been walking, help train, and taking care of dogs for some time now I love everything to do with animals! I only work part time so that gives me a lot of time to spend with your pup! I have a huge yard and am just ready to have dogs running in it! Right away in the mornings the dogs get taken outside, then it’s breakfast, and then outside some more!

Sitter Profile Image: Stefanie J.
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Stefanie J.
from
$25
per visit
4.6 out of 5 stars
9 reviews
4 repeat clients
10 years of experience
Freeport, IL, 61032

Stephanie was great. Kept in touch about our kitty every day and sent photos over text. I highly recommend

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Ann H.
Sitter Profile Image: Lisa N.
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Lisa N.
from
$31
per visit
5.0 out of 5 stars
52 reviews
12 repeat clients
20 years of experience
Freeport, IL, 61032

Great experience! Hobbes (our cat) loved Russ & Lisa and we loved the updates and pics they sent us of his stay. Thank you so much!

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Gaylene G.
Sitter Profile Image: Mackena W.
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Mackena W.
from
$11
per visit
5.0 out of 5 stars
15 reviews
6 repeat clients
15 years of experience
Darlington, WI, 53530

This was my 2nd trip away with Mackena caring for my kitty this past year. It was just 2 weeks after my other kitty passed away, so I was worried about leaving my kitty alone for a number of days under the circumstances. Mackena gave Tillie such wonderful attention and made sure she had everything she needed. I received videos and pictures of playtime, snuggle time and treat time as well as a detailed update on what happened on each visit. Would highly recommend Mackena to care for your furry friend and will definitely book with her again. Thank you SO much for the peace of mind while I was away!

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Kristin J.
Sitter Profile Image: Amber T.
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Amber T.
from
$27
per visit
5.0 out of 5 stars
6 reviews
5 repeat clients
3 years of experience
Monticello, WI, 53570

About: I've always loved animals, I work at a Veterinary Clinic as a Veterinary Assistant. I am pretty flexible with my pet sitting schedule and hard working! I am currently a full time veterinary assistant but can be very flexible around my working hours. For sittings i usually spend my time with the animal if I am not working I have a dogs and two cats at home. I also work at a veterinary clinic and know how to handle dogs and cats. Thank you.

Sitter Profile Image: Chris F.
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Chris F.
from
$18
per visit
5.0 out of 5 stars
19 reviews
4 repeat clients
1 year of experience
Sabula, IA, 52070

Chris is an amazing sitter! This was my first time using Rover and he put me right at ease. He took such good care of my kitty and sent me pictures all throughout the stay. He also left my place in great condition and was very flexible with timing. I highly recommend him!

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Maya N.
Sitter Profile Image: Lensy A.
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Lensy A.
from
$18
per visit
5.0 out of 5 stars
12 reviews
5 repeat clients
11 years of experience
Capitol, Madison, WI, 53703

About: Hi! I understand how important it is for your feline friend to feel loved and cared for in their own environment. While I don’t have a furry friend of my own, I care daily for my grandfather's two cats, Ireland and Tao, who have taught me so much about the unique personalities that cats can have. Additionally, I've gained experience caring for kittens I’ve found and nurtured until I could find them loving homes. I have hands-on experience ensuring cats get the attention they need, whether it’s feeding, playtime, or maintaining a clean and comfortable space. I recognize how important routine is for cats, so I make sure they’re fed on time, receive enough playtime, and enjoy a clean, cozy environment while you're away. Rest assured, I’m flexible and happy to accommodate any specific care routines your cat may have. Your cat’s comfort and well-being are my top priorities.

Sitter Profile Image: Kimberly S.
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Kimberly S.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
25 reviews
6 repeat clients
20 years of experience
Morrison, IL, 61270

Excellent communication and Kimberly did a great job with all of my requested items. Thank you for making my vacation less stressful! I will definitely use Kimberly again!

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Nichole G.
Sitter Profile Image: Gemma C.
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Gemma C.
from
$25
per visit
2 years of experience
rockford, IL, 61108

About: professional care for your pets. background in healthcare means i’m calm under pressure and great with meds. here to keep your cat happy and your mind at ease. 🐾

Sitter Profile Image: Teresa D.
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Teresa D.
from
$27
per visit
5.0 out of 5 stars
5 reviews
30 years of experience
Janesville, WI, 53545

Teresa took wonderful care of Ziggy. Plenty of exercise and bathroom breaks. Can’t recommend her enough! Thanks for the last minute save

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Daniel B.
Sitter Profile Image: Analj K.
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Analj K.
from
$27
per visit
5.0 out of 5 stars
9 reviews
3 repeat clients
15 years of experience
Allied Community, Madison, WI, 53711

Having Analj there made me feel a lot safer leaving my cat alone - she sent lots of photos, updates, and was great to communicate with!

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Laura C.
Sitter Profile Image: Amanda R.
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Amanda R.
from
$15
per visit
4.9 out of 5 stars
9 reviews
2 repeat clients
16 years of experience
Fitchburg, WI, 53711

About: Nice to meet you! My name is Amanda and I’m 33 years old, also a huge animal lover! I’m currently a student at Madison College, taking my online pre required classes to prepare myself towards my Veterinary Assistant Program. My primary language is English, but I also know ASL (still learning). I used to volunteer at the Dane County Humane Society while walking/exercising the dogs and interacting with the cats and other pets. I’ve been animal sitting for at least 16+ years now. I have worked at dog lovers of Madison caring while bathing pets! I worked at waggin tails in their doggy daycare department working with all sorts of dogs, and I know some training techniques as well. While I pet sit for you; I just adore taking pictures of them to send to you, so we can share with you about a few of the fun and exciting things that we’re doing while you are away! If you have anymore questions or are interested than please don’t hesitate to call or even just send me a text! I can’t wait to hear from you and I’m thrilled to meet your pet(s)! Thank you again! Here are my prices for pet sitting plus the additional $5/day (if you live out of Dane county), also my cancellation policy of a 50% fee from total cost for if it's less than 48 hours notice. If you have other pets other than a dog and cat, I will do a bundle… (2) ferrets and fish or snails (tiny pets): $15/night or drop in visit($20 for holidays) (2) ferrets: $10/night or drop in visit($15 for holidays) chickens and fish or snails (tiny pets): $25/night or drop in visit($30 holidays) Plus the additional $5/day (if you live out of Dane county), also my cancellation policy of a 50% fee from total cost for if it's less than 48 hours notice. Hangout drop in visit session for 1 hour: $30 (1-3 cats and/or dogs) Hangout drop in visit session for 2-8 hours: $50 (1-3 cats and/or dogs)

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Perfect for high energy dogs - Winslow

Prices are estimates per day. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

1 / 1
Sitter Profile Image: Sue K.
Verified Enhanced Background Check
Sue K.
from
$25
per day
30 years of experience
Orangeville, IL, 61060

About: ✨ Services I Offer 🐶 In‑Home Pet Care (At our welcoming home on 4 peaceful acres) Your pets don’t just stay with us—they vacation with us! • Daily walks, outdoor adventures, and plenty of fresh air • Cozy relaxation, cuddles, and companionship throughout the day • A clean, safe, loving environment that feels just like home—only better • Perfect for pets who thrive with extra attention and room to roam 🏡 House Sitting for Your Pets Bringing comfort and consistency right to your doorstep. • No job too big or too small—every pet gets VIP treatment • Keep your peace of mind while you’re away • I follow your pet’s routines so they stay relaxed, happy, and stress‑free • Reliable, attentive care from someone who treats your pets like family --- ❤️ Over 30 Years of Experience A lifetime of caring for dogs and cats means your pets are in loving, knowledgeable, trustworthy hands. I am independently insured as a professional pet sitter. Rover bookings are also backed by Rover’s pet‑care guarantee. Find us on FB Old Soul Pet Sitting I work from home, which means your fur babies get all‑day attention, love, and care—no long stretches alone, ever. Whether your pet is an adventurer or a casual stroller, I’ve got them covered! I walk 3–5 miles a day, so if your pup loves exploring, they’ll be right at home with me. Prefer something calmer? We also have 4 peaceful acres perfect for relaxed sniff‑sessions and easygoing walks. Trust me—there’s LOTS to sniff! Inside, your pet will enjoy premium lounging, too. I’ve set up a couch right in front of our big living‑room window so they can keep tabs on all the outdoor action. Plus, the family room and dining room both have patio doors—meaning plenty of prime viewing spots for curious noses and watchful eyes. Your pet’s comfort, happiness, and enrichment come first—and they’ll feel that from the moment they walk in the door. ❤️ Pets Are Family—And That’s Exactly How I Treat Them In my home, pets aren’t “just animals”—they’re family. Our own dogs and cats have always slept in our bed, curled up on the couch, and enjoyed every creature comfort right alongside us. I’ve had pets of all sizes throughout my life, and I truly love them all. I know how hard it can be to enjoy time away when you’re worried about your fur babies. That’s why, with me, your pets become my top priority from the moment they arrive. They’ll never be stuck in cages—just freedom, affection, and the good life they deserve! 📸 Daily Updates—Your Way Want a couple of check‑ins or all‑day photo updates? Just tell me your preference, and I’ll exceed your expectations. As a lifelong pet parent myself, I understand how important it is to know your babies are safe, happy, and having fun. 🐾 Trusted Experience You Can Count On I proudly partner with FetchWI and the Green County Humane Society, providing foster care for dogs waiting for their forever homes. Caring, patience, and compassion are at the heart of everything I do. I am independently insured as a professional pet sitter. Rover bookings are also backed by Rover’s pet‑care guarantee.

Sitter Profile Image: Lisa N.
Verified Enhanced Background Check
Lisa N.
from
$55
per day
5.0 out of 5 stars
52 reviews
12 repeat clients
20 years of experience
Freeport, IL, 61032

We are so happy we found Lisa for our puppy, Belle! Belle was very taken care of and pampered, and even came home with the cutest little bandana at the end of her week-long day care stay. Lisa and her family are wonderful, and we won’t hesitate to have Belle over the next time we need doggy day care!

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Sharon B.
Sitter Profile Image: Christine N.
Verified Background Check
Christine N.
Star Sitter
from
$34
per day
5.0 out of 5 stars
131 reviews
63 repeat clients
35 years of experience
Prairie Hills, Monticello, WI, 53570

We had an amazing first Rover experience! Christine was fantastic with Nell—kind, attentive, and very communicative. The frequent updates and photos meant so much and really put me at ease. I’m so grateful for the great care and already booked again!

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Joette & Bryan M.
Sitter Profile Image: Jilly W.
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Jilly W.
from
$37
per day
5.0 out of 5 stars
30 reviews
11 repeat clients
43 years of experience
Freeport, IL, 61032

Jolly and Kenbob are great people. After meeting and talking with Kenbob we had no qualms about leaving Bailey in trusted hands for the day. Would definitely call them again when we are in the area.

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Dan & Mary R.
Sitter Profile Image: Stefanie J.
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Stefanie J.
from
$35
per day
4.6 out of 5 stars
9 reviews
4 repeat clients
10 years of experience
Freeport, IL, 61032

Stefanie was great with our two girls. She was very attentive and definitely a dog person, but also an animal lover. Lots of room for everyone, and our puppies must have had a great time because they were exhausted when we picked them up. I can't recommend Stefanie enough.

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Chris B.
Sitter Profile Image: Hillary H.
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Hillary H.
Star Sitter
from
$25
per day
5.0 out of 5 stars
14 reviews
6 repeat clients
30 years of experience
New Glarus, WI, 53574

About: I have had animals since I was very young so lots of experience. Have owned 3 rescue dogs who are just like members of my family. Recently, I have been helping friends with their animals when they vacation and am looking to extend my client group to the local area. I am very active so walking dogs is very enjoyable for me. I am free most mornings and nights and have longer breaks during my work day that would allow flexibility for drop ins and walks all week. I am able to come to your home and provide for your pet's needs including walks, feeding, potty breaks etc. I've even been known to clean a litter box or two. Can provide references upon request.

Sitter Profile Image: Kate S.
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Kate S.
from
$60
per day
5.0 out of 5 stars
24 reviews
10 repeat clients
32 years of experience
Belleville, WI, 53508

Kate is amazing! Not only does she send you updates but she also is consistent with the training you and your dog are working on. She treated my dog like it was her own and I feel like my dog is so safe with her. Definitely going to Kate again!

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Savannah T.
Sitter Profile Image: Brenley J.
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Brenley J.
from
$25
per day
7 years of experience
Brodhead, WI, 53520

About: What sets me apart from other pet sitters is my hands-on experience and dedication. I've fed cats and dogs, walked them, and stayed overnight for extended periods. I've also trained puppies and my own dog, ensuring a well-rounded approach to pet care. Pet owners have relied on me for consistent care, knowing I’m always there when needed. My commitment to providing personalized and compassionate attention makes me a trustworthy choice for any pet sitting job. I am currently a technical college student who only goes to school twice a week while the rest is online, so I will have plenty of time to play with your pups! I am available to care for your dog Thursday-Sunday most weeks and will give them all the time they need! I like to know the pets routine/schedule and understand any behavior they may have. I would love to know the intentions of me watching your beloved doggy and what you need from me personally to make you and your dog as comfortable as possible.

Sitter Profile Image: Linda f.
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Linda f.
from
$45
per day
5.0 out of 5 stars
6 reviews
1 repeat client
40 years of experience
Elizabeth, IL, 61028

About: I have always had pets. Whether fish, cats, dogs, small birds. They are part of my family! I’m devoted! And have even resuscitated a gold fish! I work part time during the week watching my grandkids but otherwise have no obligations except to care for your fur babies and ensure your peace 😉 I will ask for instructions and follow them to ensure your pets routine and comfort is foremost beyond keeping doors shut for security. I will not use or bring other pets or materials into your home that would compromise your pets peace and safety. My children are now adults with lives of their own. So I have plenty of time for your fur babies. So, no worries. When I’m caring for your fur-baby, I will always consider your pets safety and well-being first. I understand that little dogs can be fragile. :-) I prefer to care for your pets in your home if possible. Otherwise they must be socialized and okay with my cat. My home is small but I have a yard and lots of walking available - Cats are usually drop-ins at Your home, but if in mine; because I have cats (friendly), I wiIl always see/hear them and be well-looked after. :-)

Sitter Profile Image: Ellen W.
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Ellen W.
from
$50
per day
5.0 out of 5 stars
14 reviews
2 repeat clients
12 years of experience
New Glarus, WI, 53574

About: I’ve been pet sitting for friends and family since before I could drive. You name it; dogs, cats, rabbits, chinchillas - I’ve watched them. So if you have other animals that need care, the more the merrier! I love dogs and will be as excited to give your dog a walk as they are! I can give references phone numbers upon request. I have helped train dogs and puppies throughout the years. I may even be able to teach your dog a new trick 😉 I have great patience and a calm, easy-going nature. My husband and myself have opened our home with a very large fenced in backyard to welcome your dogs. Between the two of us, your dogs will feel right at home. My husband is also certified in dog massages (yes it’s a thing! 😅) so if you have a pup with joint or mobility issues, he can assist with that as a bonus! If you are welcoming me into your home, I will be sure it looks just as good as when you left it in my care. Please send me a request to chat about your furry family member - I look forward to meeting you! I currently work part-time and my husband also has a flexible schedule to ensure your dogs have the attention they need during their stay with us. We have a comfortable environment with a large fenced in backyard for your dog to play in and have frequent potty breaks. If your dog needs their own space, we have extra rooms in the house that can be their own during their stay.

Sitter Profile Image: April S.
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April S.
from
$33
per day
5.0 out of 5 stars
3 reviews
15 years of experience
Belleville, WI, 53575

About: We are a family looking to host short term visits and love on puppies so my kids can experience taking care of dogs without the longterm commitment. We are a homeschooling family that have capacity to learn responsibility being supervised and give so much attention to puppies who need a place to stay while you travel! The intention of hosting your family pet is that they will be apart of our family while they stay with us and be loved and taken care of well instead of being kenneled.

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Adventure-ready dog walkers - Winslow

Prices are estimates per walk. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Stefanie J.
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Stefanie J.
from
$35
per walk
4.6 out of 5 stars
9 reviews
4 repeat clients
10 years of experience
Freeport, IL, 61032

About: Looking for a loving home away from home for your pet? Look no further! I'm a total animal person with a cozy place perfect for furry guests. Your pup will get lots of exercise, playtime, and all the cuddles they want. I'll keep you updated with pictures and stories so you can relax while they're having fun. I offer a safe and fun environment where your pet won't be bored and lonely or kenneled all day and night. Let's chat about your pets personality so I can make their stay paw-fect. I have a flexible schedule, please let me know what your needs are. I have a large spacious house and yard. I live near various parks and can provide a very comfortable stay for your animal while you are away. I have experience with puppies and kittens as well as the special needs of elder animals. I can provide some grooming and have over 10 years experience with animals including working at a formal dog daycare and groomer.

Sitter Profile Image: Lisa N.
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Lisa N.
from
$34
per walk
5.0 out of 5 stars
52 reviews
12 repeat clients
20 years of experience
Freeport, IL, 61032

Lisa was great! Super caring and detailed! Able to accommodate last minute requests. Thanks for caring for Ruby!

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Patty M.
Sitter Profile Image: Mia H.
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Mia H.
from
$20
per walk
5.0 out of 5 stars
2 reviews
4 years of experience
Argyle, WI, 53504

About: I have had a passion for dogs since I’ve been 11. I have been walking, help train, and taking care of dogs for some time now I love everything to do with animals! I only work part time so that gives me a lot of time to spend with your pup! I have a huge yard and am just ready to have dogs running in it! Right away in the mornings the dogs get taken outside, then it’s breakfast, and then outside some more!

Sitter Profile Image: Whitney W.
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Whitney W.
from
$40
per walk
5.0 out of 5 stars
5 reviews
15 years of experience
Monroe, WI, 53566

Whitney was great! She took our two dogs for a walk every day for 3 days and was great with them. Would highly recommend!

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Julie M.
Sitter Profile Image: Chris F.
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Chris F.
from
$21
per walk
5.0 out of 5 stars
19 reviews
4 repeat clients
3 years of experience
Sabula, IA, 52070

Very communicative ahead of the first walk!

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Luke A.
Sitter Profile Image: Bailey G.
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Bailey G.
from
$20
per walk
20 years of experience
Janesville, WI, 53548

About: What sets me apart is that I genuinely enjoy getting to know each pet’s personality and routine. I’m patient, attentive, and calm, which helps pets feel comfortable quickly, especially animals that are anxious, shy, high energy, or adjusting to a new environment. I also have experience caring for cats and dogs with different needs, including senior pets who may need a slower pace, medication reminders, extra monitoring, or simply more patience and consistency. I understand that younger pets need structure, play, and positive reinforcement, while older pets often need gentler care and close attention to comfort and routine. Because I work in a people-centered role professionally, communication and reliability are very important to me. I make it a priority to send regular updates, photos, and clear communication so owners can feel relaxed while they’re away. I treat every pet like they’re my own and want them to feel safe, cared for, and loved while you’re gone.

Sitter Profile Image: Gemma C.
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Gemma C.
from
$25
per walk
3 years of experience
rockford, IL, 61108

About: I treat every pet like they’re my own. I’m really patient, whether it’s a puppy still learning or an older pet that needs things slower and a little extra care. I’m comfortable sticking to routines, giving meds if needed, and paying attention to small changes so nothing gets missed. I want you to feel at ease while you’re away, knowing your pet is safe, cared for, and getting lots of love. my flexible school schedule allows me to easily prioritize pet care around classes, ensuring your cat receives dedicated attention and reliable visits exactly when needed. my routine focuses on maintaining their specific feeding and litter schedules while providing professional medical monitoring, play and quiet companionship without the stress of travel.

Sitter Profile Image: Analj K.
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Analj K.
from
$25
per walk
5.0 out of 5 stars
9 reviews
3 repeat clients
15 years of experience
Allied Community, Madison, WI, 53711

About: I am a very attentive and loving pet sitter :) I grew up around animals and often found myself pet sitting for people in the community throughout my life! I’m happy to accommodate a range of pet parent preferences! From dog walking to house sitting to administering medications, I am confident in my ability to keep your pet baby happy, healthy, and well loved whenever you need the support! I currently nanny from 12:30-4:30 Monday-Friday, so I have a lot of free time to come and spend with your pet! I’m happy to go for morning or afternoon walks, or fill whatever role you need fulfilled during my open schedule! I will come to your home after we discuss what expectations you have for pet care :) I’ll happily keep your pet company while keeping them safe and healthy and well cared for!

Sitter Profile Image: Amanda R.
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Amanda R.
from
$20
per walk
4.9 out of 5 stars
9 reviews
2 repeat clients
16 years of experience
Fitchburg, WI, 53711

Amanda did a wonderful job working with my dog. She is great at communicating with me, flexible, and reliable. My dog is very timid and slow to warm up to people, but she instantly approved of Amanda and bonded quickly!

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Jacob M.
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Over 980,000
dogs traded couch time for play time with Doggy Day Care on Rover1

Large dog specialists near you - Winslow

Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Christine N.
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Christine N.
Star Sitter
from
$41
per night
5.0 out of 5 stars
131 reviews
63 repeat clients
35 years of experience
Prairie Hills, Monticello, WI, 53570

Once again Joey's stay with Christine was a great success. Christine has a ton of dog experience and it shows, she handles Joey effortlessly and helps her to adjust to staying with other dogs. We will definitely book again in the future!

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Paula D.
Sitter Profile Image: Dan W.
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Dan W.
Star Sitter
from
$25
per night
4.9 out of 5 stars
76 reviews
28 repeat clients
15 years of experience
Mineral Point, WI, 53565

Boomer had a great time with Dan! We appreciate that he took the time to do a meet and greet beforehand and showed us around the space. When we picked Boomer up, it was clear he had a good time and really tuckered out! Thanks again Dan.

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Matt & Kendra S.
Sitter Profile Image: Mary S.
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Mary S.
Star Sitter
from
$30
per night
5.0 out of 5 stars
93 reviews
38 repeat clients
20 years of experience
Lake Summerset, IL, 61019

Mary and her husband are absolutely wonderful caregivers! I received daily updates about my Ivy and they were very sweet, loving and caring with her. I highly recommend Mary to anyone who needs to be able to trust 100% that their fur babies will be well cared for!

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Angela F.
Sitter Profile Image: Jilly W.
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Jilly W.
from
$37
per night
5.0 out of 5 stars
30 reviews
11 repeat clients
43 years of experience
Freeport, IL, 61032

Jilly was great! We appreciated her quick response to our request. Charlie seemed to really enjoy his stay at the farm. Jilly also shared updates and photos with us which was really nice.

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Rose M.
Sitter Profile Image: Kate S.
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Kate S.
from
$75
per night
5.0 out of 5 stars
24 reviews
10 repeat clients
32 years of experience
Belleville, WI, 53508

Teddy had a great stay with Kate! We loved getting photo updates, and it was such a thoughtful touch that she sent him home with his favorite toy (Patrick Star!) and a goodie bag. We’ll definitely be reaching out to Kate again in the future.

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Kiersten B.
Sitter Profile Image: Lisa N.
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Lisa N.
from
$74
per night
5.0 out of 5 stars
52 reviews
12 repeat clients
20 years of experience
Freeport, IL, 61032

Lisa and her family watched our standard poodle for a weekend and did a fantastic job. She posted regular updates (with photos) and treated our pup as one of her own.

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Arzhange S.
Sitter Profile Image: Sue K.
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Sue K.
from
$25
per night
30 years of experience
Orangeville, IL, 61060

About: ✨ Services I Offer 🐶 In‑Home Pet Care (At our welcoming home on 4 peaceful acres) Your pets don’t just stay with us—they vacation with us! • Daily walks, outdoor adventures, and plenty of fresh air • Cozy relaxation, cuddles, and companionship throughout the day • A clean, safe, loving environment that feels just like home—only better • Perfect for pets who thrive with extra attention and room to roam 🏡 House Sitting for Your Pets Bringing comfort and consistency right to your doorstep. • No job too big or too small—every pet gets VIP treatment • Keep your peace of mind while you’re away • I follow your pet’s routines so they stay relaxed, happy, and stress‑free • Reliable, attentive care from someone who treats your pets like family --- ❤️ Over 30 Years of Experience A lifetime of caring for dogs and cats means your pets are in loving, knowledgeable, trustworthy hands. I am independently insured as a professional pet sitter. Rover bookings are also backed by Rover’s pet‑care guarantee. Find us on FB Old Soul Pet Sitting I work from home, which means your fur babies get all‑day attention, love, and care—no long stretches alone, ever. Whether your pet is an adventurer or a casual stroller, I’ve got them covered! I walk 3–5 miles a day, so if your pup loves exploring, they’ll be right at home with me. Prefer something calmer? We also have 4 peaceful acres perfect for relaxed sniff‑sessions and easygoing walks. Trust me—there’s LOTS to sniff! Inside, your pet will enjoy premium lounging, too. I’ve set up a couch right in front of our big living‑room window so they can keep tabs on all the outdoor action. Plus, the family room and dining room both have patio doors—meaning plenty of prime viewing spots for curious noses and watchful eyes. Your pet’s comfort, happiness, and enrichment come first—and they’ll feel that from the moment they walk in the door. ❤️ Pets Are Family—And That’s Exactly How I Treat Them In my home, pets aren’t “just animals”—they’re family. Our own dogs and cats have always slept in our bed, curled up on the couch, and enjoyed every creature comfort right alongside us. I’ve had pets of all sizes throughout my life, and I truly love them all. I know how hard it can be to enjoy time away when you’re worried about your fur babies. That’s why, with me, your pets become my top priority from the moment they arrive. They’ll never be stuck in cages—just freedom, affection, and the good life they deserve! 📸 Daily Updates—Your Way Want a couple of check‑ins or all‑day photo updates? Just tell me your preference, and I’ll exceed your expectations. As a lifelong pet parent myself, I understand how important it is to know your babies are safe, happy, and having fun. 🐾 Trusted Experience You Can Count On I proudly partner with FetchWI and the Green County Humane Society, providing foster care for dogs waiting for their forever homes. Caring, patience, and compassion are at the heart of everything I do. I am independently insured as a professional pet sitter. Rover bookings are also backed by Rover’s pet‑care guarantee.

Sitter Profile Image: Stefanie J.
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Stefanie J.
from
$50
per night
4.6 out of 5 stars
9 reviews
4 repeat clients
10 years of experience
Freeport, IL, 61032

Stefanie was great with Luna. Sent pictures and kept me updated! I felt at ease knowing Luna was being loved in a pet friendly home while I was away. Thank you!

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Amy K.
Sitter Profile Image: Isabella F.
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Isabella F.
from
$55
per night
8 years of experience
Monroe, WI, 53566

About: Hi, I’m Izzy! I’ve been a professional dog trainer for nearly 4 years, with 8 years of animal care, and am KPA-CCT certified, an AKC evaluator, and experienced with both pet and working dogs. I offer pet sitting and boarding that blends comfort with structure. Your dog will get personalized care, enrichment, and positive experiences while you’re away. Whether you have a high energy puppy or a dog in training, I ensure they stay safe, happy, and well mannered. I currently make my own schedule, with the exception of Fridays, where I’m busy from 1pm-6pm. I love to hike and jog trails, so I typically take my pets with. I also have a pond where we swim in the summer. Safety is always my top priority. I maintain a secure, dog-friendly environment where every pet is supervised and set up for success. I manage introductions carefully, use gates and crates when needed, and never leave dogs unattended together. My home is fully fenced, and I monitor play to ensure everyone stays happy and stress-free. I also follow each owner’s feeding, medication, and training routines closely to keep things consistent and safe.

Sitter Profile Image: Ashley & Timothy L.
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Ashley & Timothy L.
from
$30
per night
20 years of experience
Rock City, IL, 61070

About: We have had a dog or dogs for over 20 years. My husband and I both grew up with dogs as well. Our two dogs have been with us since they were puppies and both of them attended three levels of dog training classes. I work part-time very early in the morning and we spend a lot of time at home because my kids are homeschooled. There is usually always someone at home. I will do as much as I can to accommodate the dog owner’s preference in care for their dog. We have two dogs that can play with your dog. If your dog needs to be in a crate I can accommodate that. Our dogs are not allowed on the couches and chairs but my children do let them sleep in their beds.

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