Dog Sitting Winthrop Harbor

Book a Winthrop Harbor dog sitter to watch your dog in your sitter’s home or yours.

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

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Sitter Profile Image: Danielle M.
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Danielle M.
from
$20
per visit
1 repeat client
17 years of experience
Union Grove, WI, 53182

About: I have experience in cat sitting with clients, some of them had anxious cats that were more on the spicy side. I gained their trust and surprised their owners when they found out how close and cuddly they got with me, that's my quality. I don't expect every cat to open all of their boundaries and I respect doing what they want. 😸 I am known to socialize with the cats outside of just feeding them and cleaning their litterbox. I have had 3 cats of my own, 2 which have been elderly cats who needed medicine and careful care. 💊 I am very good at administering meds and staying consistent. I have had two dogs which both crossed the rainbow bridge from elderly age (a malamute and a newfoundland). I am an equal cat and dog lover! I would love to have a dog again one day. I walk with a cane so I am comfortable walking small dogs. 🐶 I have a very flexible schedule since I work from home. I can stop by any time in the mornings, afternoons, and also early evenings. When going to a client's home, I am very careful when entering and exiting the home when the door opens. I also do a head count of any cats including my own before leaving a house. I know from my own pet that they like to get curious and can suddenly go into a bathroom or closet and can get closed in. Just like my teaching days - taking head counts is important! I also watch the pets as they eat especially if there are multiple in a house so that they don't overeat by sneaking snacks from their pet buddies food.

Sitter Profile Image: Rachel F.
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Rachel F.
from
$20
per visit
5.0 out of 5 stars
• 4 reviews
2 repeat clients
5 years of experience
Grayslake, IL, 60030

About: Hello, I’ve taken care of dogs and cats of every kind since I was 10 years old. I have watched, played, fed and walked friends or neighbors animals. I love and care for any size animal. My family used to own a 200+ English mastiff. I work Monday through Friday from 10:00 a.m. to 6:00 p.m., so pet care is part of my routine before and after work. In the mornings, I feed, walk, and spend time with pets before leaving. After work, I take them for another walk, feed them if needed, play with them, and make sure they have plenty of attention. On weekends, I have more flexibility for feeding, longer walks or other activities. I have a fenced in yard and walking paths all around in my neighborhood. I also have an open field near by to play fetch.

Sitter Profile Image: Devin R.
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Devin R.
from
$17
per visit
5.0 out of 5 stars
• 14 reviews
2 repeat clients
10 years of experience
Antioch, IL, 60002

“Very reliable and punctual sitter. She took very good care of our pups while we were away and gave them lots of extra love and attention. I would highly recommend her”

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Pamela M.
Sitter Profile Image: Monica L.
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Monica L.
Star Sitter
from
$40
per visit
5.0 out of 5 stars
• 41 reviews
13 repeat clients
12 years of experience
Racine, WI, 53402

“Monica was again, able to provide 5-star sitter services for my Big Guy. Long walks, drop in visits, feedings, pictures and great communication. I would highly recommend her for pet care needs. Thank you again Monica, Ripley is so happy when you visit him!”

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Miller H.
Sitter Profile Image: MaKenna K.
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MaKenna K.
from
$20
per visit
5.0 out of 5 stars
• 2 reviews
16 years of experience
Lake Villa, IL, 60046

About: I have 16 years of experience caring for others' animals. I worked for multiple horse farms until graduating college and all types of animals. Horses, donkeys, cows, big dogs, little dogs, pigs, bunnies, birds, I've taken care of them all! The bigger the animal the more comfortable I am with them. I work full time but I have a hybrid schedule that I make. I travel all over Cook/Kenosha/McHenry/Lake/Dupage Counties so if you're in that area I can tailor my schedule to spend more time in that area the week you need to accommodate your pets needs with daily walks or overnights. I treat all pets like they are my own. I take the time to get to know what they like so they warm up to me. Their favorite napping spots or where they like to be scratched. I want them to feel as comfortable as they can be while their owner is not around. I try to be the fun aunt that comes to visit so they don't notice mom and dad are gone.

Sitter Profile Image: Katherine L.
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Katherine L.
from
$28
per visit
5.0 out of 5 stars
• 15 reviews
7 repeat clients
7 years of experience
Libertyville, IL, 60048

“Katy is super! My pup Kia really gets along with her. She is kind and helpful and communicates well. She writes me long blurbs about her time with Kia which I love since I’m not able to be with her throughout the day.”

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Roxanne H.
Sitter Profile Image: Alex N.
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Alex N.
from
$50
per visit
5.0 out of 5 stars
• 1 review
1 repeat client
3 years of experience
Lindenhurst, IL, 60046

About: I love both dogs and cats! I've never had a problem with any one of them except for that one dog that keep barking and running after me when I was 10 lol, but turned out the little guy just wanted to be friends. I am planning on doing this full time, so I'll have all the time in the world to play with your pets and to make them my besties. There is a park near my apartment that will have your pets tail wagging whenever we go for a super fun and exciting walk !

Sitter Profile Image: Krystal D.
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Krystal D.
from
$30
per visit
5.0 out of 5 stars
• 43 reviews
12 repeat clients
6 years of experience
Mundelein, IL, 60060

“Krystal did a FANTASTIC job with our cats. One of which is not usually friendly / kind, he warmed up to her quickly and was even walking on her lap! You can feel 100% confident that Krystal will take great care of your furry friends. Will be back time & time again to work with her when we need help with the cats!”

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Michelle K.
Sitter Profile Image: Lauren W.
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Lauren W.
from
$21
per visit
5.0 out of 5 stars
• 4 reviews
3 repeat clients
30 years of experience
Highland Park, IL, 60035

About: I’ve taken care of and loved dogs and cats of all ages and sizes. From puppies/kittens to seniors and in between. And all sizes! I also have experience with special needs dogs, including my own collie who had lower jaw removal surgery. I’ve had 2 cats in this time from when they were young to seniors. I recently adopted 2 young cats who love people. For dogs, I’ve adopted dogs of all different ages with various health needs. I only occasionally go into the office and work from home Mon - Fri. I’m used to having multiple animals so I’m comfortable with whatever their schedule may need. I want to follow the routine you have created and anything else to make sure they feel comfortable in my home or yours. They will get lots of love and attention from me during our time together!

Sitter Profile Image: Pearl & Brady K.
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Pearl & Brady K.
from
$25
per visit
20 years of experience
Caledonia, WI, 53108

About: My husband and I are workampers! That means we move every season to a new campground and work there. This time, we are at Jellystone Caledonia!! We love to have the presence of animals, since it gets boring living in a campground without an animal to walk. There is a great dog park here with great socialization opportunities (for us and the dogs 😆😆)!! I would love an opportunity to pet sit any type of fur babies, I grew up with cats and dogs my whole life!!! If you have any questions, please feel free to reach out!! Pet care fits seamlessly into our routine. My husband and I travel full time, which gives us a very flexible schedule and plenty of availability. We both enjoy meeting new people and animals along the way, and our lifestyle allows us to be present, attentive, and adaptable. Caring for pets fits easily into our daily life and is something we LOVE. I care for pets by following their established routines as closely as possible so they feel safe and comfortable. In a client’s home, I make sure feeding schedules, walks, litter care, playtime, and medications (if needed) are handled consistently and with attention to detail. I respect the home and keep everything clean and orderly while you’re away.

Sitter Profile Image: Nikita H.
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Nikita H.
from
$30
per visit
5.0 out of 5 stars
• 1 review
5 years of experience
Glenview, IL, 60026

About: I’ve been around dogs since I was a kid but a few years ago, I started to help my boyfriend in bathing, feeding, walking, and taking care of his dog. Since then, I have also started watching dogs for my friends and family members when they need assistance. I am currently available all day, any day to take care of pets as I work remotely and have flexibility in my day to day schedule. I would care for pets in my home by spending time with them, feeding them, walking them, and making sure that they have fun for the duration of their stay :)

Sitter Profile Image: Michelle L.
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Michelle L.
from
$17
per visit
10 years of experience
Des Plaines, IL, 60016

About: I have been in charge of taking care of the family dog since I was 11. I have in depth experience in training, walking, and cleaning pets. I currently work remote so it is convenient for me to take care of pets on a daily basis. I am available most times throughout the day. I have a fenced yard with lots of space for pets to run and play. My neighborhood is very safe and pet friendly. I keep my home safe and clean.

Sitter Profile Image: Noah M.
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Noah M.
from
$23
per visit
10 years of experience
Lake Geneva, WI, 53191

About: I've had dogs since I was little. Love pets. I go for walks daily so a furry friends to assist me in these walks in ideal! Growing up we had two dogs since puppies and rescued an older dog! I am a natural care taker who loves animals! I am a teacher during the year so I am available all summer! Morning, afternoons, evenings! Weekend can get busier, but I am a flexible go with the flow person! Letting dogs out, watching them in the yard, leasing them up, taking them on walks, making sure they are fed and hydrated, occasional treats, all up my alley.

Sitter Profile Image: Joshua M.
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Joshua M.
from
$30
per visit
1 repeat client
6 years of experience
Chicago, IL, 60630

About: I have owned and loved dogs and cats my entire life. I am currently a Canine Handler/Trainer/Decoy for Dunlap Security and Dog Training. I specialize in obedience and personal protection/k9 decoy work. I have also had experience working with Chasing Tails 4 U Inc. as a dog handler/ play supervisor. I especially love the big mastiffs and bully breeds but am comfortable around all dogs big and small. I look forwards to working with your Dogs and Cats At the moment this is my full-time job. 24hrs of my day is dedicated to dogs and becoming a dog trainer and decoy. I’m at your service I am available to take dogs to dog parks beaches etc. of play dates where I come take your pet todo a day full of fun dog activities.

Sitter Profile Image: Jayla V.
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Jayla V.
from
$17
per visit
5.0 out of 5 stars
• 6 reviews
1 repeat client
10 years of experience
River Grove, IL, 60171

About: Experience with all kinds of pets and reptiles. Will be treated with upmost care. I can provide a number of services including bathing, walking, feeding, cutting nails/grooming and any special requests from you. I do work a full time job between the hours of 6am and 3pm but any time after that I am free to tend to any needs you or your pet needs. I will have a designated play area for your fur babies if any needed. I will update with pictures and calls if needed. I will follow any schedule given.

Sitter Profile Image: Rachel N.
Verified Enhanced Background Check
Rachel N.
from
$25
per visit
1 repeat client
1 year of experience
Rogers Park, Chicago, IL, 60626

About: I grew up with pets such as cats, guinea pigs, rabbits, etc I also have ridden horses and taking lessons up until I’ve moved here. My experience with dogs has been taking care of, feeding, and walking my cousins dogs while I lived with them until 2023. I work a 9-5 but have a bit of flexibility, I live in the downtown area so looking for early morning or late afternoon walks or overnight stays/checks if needed! I would definitely want to set expectations up front even if it involves written requirements. I would also suggest sharing location, or having a tracking device for peace of mind when I am with your dog and transparency on both ends. I prefer to set up a meeting beforehand to meet each other and see if it’s a good match!

Sitter Profile Image: Alexandria F.
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Alexandria F.
from
$28
per visit
8 years of experience
Woodstock, IL, 60098

About: It all started out with my love for animals when I was younger. I started out my career in grooming than transferred over to a veterinarian assistant and became a veterinarian technician. I have over 8+ years experience with dogs and cats in the professional setting. I also have two dogs and one cat of my own that I love dearly. I currently got laid off my day job so I’ll have plenty of time to hang out,play,walk, give treats etc. Thank you for reading my profile. I won’t be offering in my home services due to my animals. When it comes to your pets I will play, walk, feed, kennel ect. Per your instructions

Sitter Profile Image: Angelina F.
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Angelina F.
from
$17
per visit
1 year of experience
O'hare, Chicago, IL, 60656

About: I have taken care of my friend's pitbull. His name is Blue and he is the cutest most dog ever. If I could post a picture of him, I would. But I would take care of their dogs when they went on vacations or on work trips. I would go into their house to feed, clean, and play with blue. The owner would want me to take a picture of blue every time I went. They would be out for a while, so I had to stay the night, or I would pick up blue and take him to the park or Starbucks for a pup cup. Blue was not the only pets they had! They had a cat and bunnies, so I did go out to their coops and feed, clean, and take care of any other responsibilities needs with the animals. The cat named lea that would not stop talking when I entered. I did the same for her as the other animals feed, care, and play. I am a flight attendant and I am flexible. I have a couple of days off during the week. We can communicate my schedule even a month in advance because we are awarded our schedule every 18th of every month. On my days off I can start early, mid-day, late, let talk about it :D If there is a certain way that the animal needs to be taken care of, I take the precautions and care for that animal. For example, blue the animal I took care for my friend stool was watery she told me it happens a lot because he either eating too much or he is lonely. So, at first, I was giving him less of what he is used to and the problem persisted. Next action was to spend more time with blue, and I did that and his stool improved.

Sitter Profile Image: Devin V.
Verified Enhanced Background Check
Devin V.
from
$16
per visit
10 years of experience
Elkhorn, WI, 53121

About: I've had a love/passion for dogs since I was born into this life. Growing up, I've always had a dog in the house, so it easily became the norm for me. I have experience with a wide variety of breeds, including doberman, pitbulls, great dane, labs, boxers, beagles, and mutts. I truly love them all. I'm open to taking care of all breeds. I don't discriminate! One thing I will note is that I specialize in high energy/working dogs and am very familiar with larger breeds. Just to give you a quick example, I raised a Doberman from a puppy which led to me learning A LOT throughout the process. Doberman are a working breed and require plenty of mental and physical stimulation & I think I cracked the code! I’ve developed a deep understanding of what high-energy dogs need to thrive. I'm good at stimulating their minds, keeping them active and most importantly, happy. I'm not a certified dog trainer, but I do understand the importance of balancing their physical and mental well-being, and I'm dedicated to ensuring each dog has a great time with me! I'm very engaging and mindful, so whatever your dog may need, whether it's staying active outside or relaxing at home, I will do my best to provide. That's a promise. When it comes to availability, I am free at the moment. You can contact me any time and I will get back to you asap. I will make sure you feel comfortable with leaving your pets with me. To ensure you of this, I will send you daily photos & videos to show you how good of a time they're having! Also, you can give me a call ANYTIME. I know what it's like to drop my dogs off at a pet sitter's house, so my job is to give you the relief of knowing that your pets are in great hands. I can guarantee you this🙂

Sitter Profile Image: Kiana L.
Verified Enhanced Background Check
Kiana L.
from
$30
per visit
15 years of experience
Lake View, Chicago, IL, 60657

About: I have taken care of my dog for 15+ years until he passed away recently and look forward to taking care of your dog with the same car. I work full time 9am to 5pm Monday through Friday but I am available on weekends or nights to take care of your dog. :) I am Offering dog walking services and look forward to meeting your dog and providing proper care. Excited to meet your dog and go for walks

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The median cost per visit for dog sitting in Winthrop Harbor is $21

Dog parents share their Rover experiences - Winthrop Harbor

1 / 1
5.0 out of 5 stars

Absolutely wonderful with my boys while I was out of town. My nervous one was super comfortable with her, which is always huge for me. Lots of notes and pictures to keep me updated. Will definitely book again.

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Erin M.
Drop-In Visits
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Popular requests for dog sitting - Winthrop Harbor

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Sitters in Winthrop Harbor average 7
repeat dog sitting clients

FAQs for Dog Sitting - Winthrop Harbor

Frequently asked questions about Rover

The average cost of Dog Sitting in Winthrop Harbor is $17 per visit as of November 2026. Most bookings cost between $17 and $19 per visit. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

As of November 2026, there are 3,771 sitters on Rover offering Dog Sitting across Winthrop Harbor. Enter your ZIP code to see which available sitters are closest to your home.

You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.

Before booking, confirm:

  • the timing, length, and frequency of visits;
  • the care instructions the sitter should follow;
  • which parts of your pet’s usual routine should be prioritized;
  • how often you would like to receive messages, photos, or other updates.

Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.

Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Winthrop Harbor choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!

Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page.

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the Rover Guarantee, which provides up to $25,000 in eligible veterinary care reimbursement.

A Meet & Greet is a casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.

Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet or the new environment.

During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first Meet & Greet.

While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.

To find sitters in Winthrop Harbor with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.

Yes, you can find sitters who have experience with handling special pet needs in Winthrop Harbor. On Rover:

  • 88% of sitters can help with special care needs
  • 92% can help with giving oral medications or injections
  • 94% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

sitters on Rover set their own cancellation policy, which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.

Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.

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