Dog Sitting Windsor

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

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Over 95
pet parents in Windsor have booked dog sitting

Windsor, Find top rated dog sitting

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: Tonisha A.
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Tonisha A.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
49 reviews
12 repeat clients
30 years of experience
Sun Prairie, WI, 53590

Tonisha had a short visit with my pup but did exactly what I asked of her and kept communication going through out her visit, would definitely hire her again!

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Megan B.
Sitter Profile Image: Christopher G.
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Christopher G.
from
$15
per visit
5.0 out of 5 stars
10 reviews
3 repeat clients
15 years of experience
Deforest, WI, 53532

Chris was awesome with my boy Monty! He was quick to respond, attentive, and I felt so comfortable knowing he was going to be with my pup. Monty was in great hands. 10/10 recommend, thanks Chris!

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Marc Z.
Sitter Profile Image: Chelsea B.
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Chelsea B.
from
$15
per visit
5.0 out of 5 stars
3 reviews
1 repeat client
15 years of experience
High Crossing, Madison, WI, 53718

Chelsea was kind enough to visit our cat on short notice. She did a great job visiting with Blue, sent us lots of photos, detailed updates, and our cat loved her!! We definitely recommend her :)

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Helen M.
Sitter Profile Image: Madeline S.
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Madeline S.
from
$15
per visit
15 years of experience
Sun Prairie, WI, 53590

About: I’ve had dogs in my life for as long as I can remember. I grew up with dogs at home, and over the past 15+ years that love has turned into real hands-on experience: feeding schedules, potty training quirks, senior dog needs, high-energy breeds who need a good run, and the anxious pets who just want a lap to curl up on. I treat every dog I care for like my own. Whether it’s a quick drop-in visit or an overnight stay, your dog will get consistent care and lots of love. I’m reliable, communicative (expect photo updates!), and genuinely happiest when there’s a dog nearby. Looking forward to meeting you and your pup! I’m currently waiting for my full-time job to start so I’ll have plenty of time to spend time with your pets! They will get lots of love and attention. I plan to make sure your pets always feel safe and comfortable! They will always be my top priority and meeting their needs will be essential.

Sitter Profile Image: Michelle H.
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Michelle H.
from
$20
per visit
5.0 out of 5 stars
4 reviews
2 repeat clients
23 years of experience
DeForest, WI, 53532

About: Lifelong (35 years) dog lover and owner of a golden retriever. I begged my parents growing up to get our family a dog...luckily after all of my persistence, my mom and dad finally gave in. My family got two dogs within a few weeks of one another, a Chocolate Lab and a Brittany. Both had a lot of energy and were very loving. Of course, the dogs came with the responsibilities which I happily took on. I loved taking them for walks, meal time, playing fetch in the yard, and even the poop scoopin' duties. Currently, I work from home and get to spend all day with my golden retriever Stark. I want to help the other working dog moms and dads in my community who don't have the luxury of being home with their dog every day. If you want help to take your dog out to go potty, go for a walk, snuggle, just visit, or play, then I'm the one for you!! I work from home and can be available as needed as long as it's not during a scheduled conference call - gotta keep my day job. I'm pretty flexible but also don't mind a routine schedule if that would benefit you. If any dog steps it's paws in to my home or yard, I'll treat them like a part of my own family. Just seeing a dog puts a smile on my face. I have a large home with wood floors. There's also a large nearby fenced-in dog park a few miles from my house where I take my golden retriever to really run off the zoomies. I love my dog and I'm obsessed with him. Every photo on my phone is of my dog, my kids, or food, the three loves of my life...oh and my husband, he's got a few photos in there too.

Sitter Profile Image: Kris A.
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Kris A.
from
$15
per visit
5.0 out of 5 stars
13 reviews
4 repeat clients
16 years of experience
DeForest, WI, 53532

About: I'm currently in a pet-free home with my kiddos and have lived with dogs for much of my adult life. I'm a massage therapist and love giving pups a little TLC with energy therapy and light massage. They love it! The dog you see in my thumbnail photo is KC. She was a rescue dog who was with us for six years and needed lots of training, support and care. Please note I take 3 walking clients per day but only 1 boarder at a time. I teach at a technical college and am a personal trainer, working part-time from home and part-time out of the home. I'm often home for long hours during the day. My three kids are in public school, so dogs may have 1 to 4 dog-lovers in the home after 4pm. I offer long walks on sidewalks or trails if preferred, treats, water, lots of play and unlimited petting! I offer care in my home and dog walking. Pets are allowed on my furniture if that's what they're used to. Looking forward to meeting your pup!

Sitter Profile Image: Tina B.
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Tina B.
Star Sitter
from
$25
per visit
4.9 out of 5 stars
77 reviews
22 repeat clients
38 years of experience
Waunakee, WI, 53597

I know I can always count on Tina to provide excellent care. We have three cats who are needy for attention and Tina always comes through with photos!

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Morgan B.
Sitter Profile Image: Gwen K.
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Gwen K.
from
$22
per visit
5.0 out of 5 stars
3 reviews
4 years of experience
Windsor, WI, 53598

About: I have worked at three different doggy daycare and boarding businesses within the past four years. I have been dog sitting for family and friends for years! I treat every dog as my own! I currently work a very part-time job (2 days a week). This allows me the perfect amount of time to care for furry friends of all kinds! I live in a neighborhood with a sidewalk, perfect for walks! I don’t have any children, just one cat who is very friendly and playful with other dogs and cats!

Sitter Profile Image: Mary W.
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Mary W.
from
$14
per visit
5.0 out of 5 stars
8 reviews
5 repeat clients
20 years of experience
High Crossing, Madison, WI, 53718

Mary did a great job with my two kitties. They were both quite happy and healthy when I got back home.

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Tom W.
Sitter Profile Image: Eastyn L.
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Eastyn L.
from
$15
per visit
5.0 out of 5 stars
15 reviews
7 repeat clients
10 years of experience
DeForest, WI, 53532

Eastyn is awesome! She is super attentive and communicative, as well as on top of pictures. I felt really comfortable leaving my kitties in her very capable hands.

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Emily Z.
Sitter Profile Image: Emily L.
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Emily L.
from
$20
per visit
5.0 out of 5 stars
26 reviews
9 repeat clients
25 years of experience
Sun Prairie, WI, 53590

Emily was so wonderful and kind while checking in on our two cats while we were out of town. She was a fabulous communicator and listened to all of the instructions we left her. We would highly recommend Emily to all pet parents! :)

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Erin T.
Sitter Profile Image: Carley T.
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Carley T.
from
$19
per visit
5.0 out of 5 stars
9 reviews
4 repeat clients
20 years of experience
Westchester Gardens, Madison, WI, 53704

Carley is a delight and such a wonderful sitter! Incredibly sweet and a natural with animals, I had no worry at all leaving my pups in her care. Regular check-ins and photo updates throughout the weekend. I highly recommend Carley and will definitely try to book her again.

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Suzanne S.
Sitter Profile Image: Allison B.
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Allison B.
from
$20
per visit
5.0 out of 5 stars
5 reviews
1 repeat client
4 years of experience
Sun Prairie, WI, 53590

Allison was so incredibly helpful with this stay. Our plans shifted several times, but she was very patient with us throughout the changes. She took great care of our pups and left detailed notes for each visit

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Madison W.
Sitter Profile Image: Maria & Bryan P.
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Maria & Bryan P.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
4 reviews
2 repeat clients
30 years of experience
Waunakee, WI, 53597

About: We have been loving and caring for dogs for a long time. Big and small dogs; young and old. Our son and 7 year old dog are welcoming I am currently working from home and Bryan works part time. Our son is home schooled at this time, therefore, we have time and energy to help other dogs and other families We have a large yard in a quiet neighborhood; part of our yard is fenced and other part is open for additional exercise. We also walk our dog daily.

Sitter Profile Image: Carrie R.
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Carrie R.
from
$13
per visit
18 years of experience
Deforest, WI, 53532

About: I grew up on a farm and around animals my whole life. I’ve dog sat for many friends and family members of mine and would love to be able to look after yours. I work in the mornings and I am home by noon most days and am around all weekend to look after any pets. I go for long walks most days. I have a large, in fenced backyard and I am close to the park and walking trails. I also love to go hiking and would like to able to take dogs with too.

Sitter Profile Image: Kelsey T.
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Kelsey T.
from
$18
per visit
5.0 out of 5 stars
25 reviews
7 repeat clients
2 years of experience
Sun Prairie, WI, 53590

Kelsey was amazing with our new pupper and followed all the instructions asked of her. She and Osa had a great time and Kelsey was sure to send thorough updates and pictures as well. While Osa was very excited to see us that evening, she definitely made a new friend today!

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Nick R.
Sitter Profile Image: Kristina D.
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Kristina D.
from
$22
per visit
20 years of experience
Waunakee, WI, 53597

About: Dogs are my favorite people - I attract dogs wherever I go. I have owned two dogs in my adult life-English Bulldog and Goldendoodle. Currently, I have a 10 year old goldendoodle. She loves everyone. I am a teacher and have off during the summer. I enjoy hiking, camping, biking, running, reading, gardening, and cooking. I’m currently on summer break, so my days are very flexible. During the school year, I am available before 7am or after 4pm. I have a very friendly goldendoodle. I have a big yard. I am willing to provide lots of love, playtime, and walks for your dog. I can be active with your pet or sit with them and love them up. Whatever you need, I can provide.

Sitter Profile Image: Renee L.
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Renee L.
from
$22
per visit
5.0 out of 5 stars
8 reviews
3 repeat clients
20 years of experience
Sun Prairie, WI, 53590

About: I have been around animals all my life and even gravitate towards animals versus people in most social situations. I have cared for small Poodles and Terriers, as well as Labs and Great Danes. When I was in middle school, I taught my Golden Retriever obedience and agility. I put 110% effort into all jobs I am hired for because it’s truly something I love. I am an active individual who also loves to snuggle up on the couch with a good book. So whether your pet is an active walker or a cuddly couch potato, I promise to provide them with the love care they need while you are away. I can't wait to sit for your family and help ease your worry while you’re away! Before going to work as a teacher, I would make sure to check in on your pet in the morning. Feed them, take them potty, and depending on time take them for a morning walk. Directly after work, I would go home to see my cat Benny, and then go visit your house. I’ll make sure that your pup is fed, goes on a walk, or has a great amount of playtime and snuggles! Before taking them outside at your house, I would make sure that your dog is either on a leash, the yard fence is closed, or their recall is good with me. Most importantly, I want to make sure that in a new situation and with someone new in their home, they somehow do not get loose.

Sitter Profile Image: Kyle S.
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Kyle S.
from
$15
per visit
15 years of experience
Sun Prairie, WI, 53590

About: I bring over 10 years of hands-on professional experience in the veterinary field, along with more than 30 years of daily life caring for cats and dogs. I’m comfortable working with pets of all temperaments, including shy or reactive dogs, and I have experience caring for elderly, disabled, and special needs animals. I’m skilled in administering medications (can give injections) and monitoring for signs of illness or distress, so you can feel confident your pet’s health is in good hands. Beyond medical care, there’s nothing I love more than becoming your pets best friend and providing the enrichment and attention they need. Whether that is long walks and playtime or calm companionship and cuddles. I’m happy to reinforce basic training cues, provide regular updates with photos, and keep your home in order while you’re away. My goal is to provide reliable, compassionate care so your pets feel safe, happy, and loved while you’re gone. Currently I am lucky enough to have full control over my schedule and will always make time for walks! There’s no activity I love more than hanging out with dogs and going on walks. Your pet’s safety and comfort are always my top priority. With over a decade of professional veterinary experience, I know how to handle pets calmly and safely in a variety of situations. I’m comfortable managing pets with medical needs, special care requirements, or challenging temperaments, and I keep a close eye on their well-being at all times. I believe communication builds trust, so I provide regular updates and photos to give you peace of mind while you’re away. I treat every pet as if they were my own, with patience, respect, and care. You can count on me to follow your instructions closely and to create a secure, loving environment for your furry family members.

Sitter Profile Image: Jackie G.
Verified Background Check
Jackie G.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
62 reviews
17 repeat clients
20 years of experience
Madison, WI, 53718

Jackie was a perfect fit for my drop in visits and day care. She was thorough in getting to know Apollo and his needs. She followed my recommendations and went above and beyond to make sure Apollo was taken care of, some people are just naturals when it comes to caring for pets, and I believe Jackie is one of them, 100/10 recommend!

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Megan B.
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The median cost per visit for dog sitting in Windsor is $20

Dog parents share their Rover experiences - Windsor

1 / 1
5.0 out of 5 stars

This was my (and my girls’!) first time using the Rover app and Heather was outstanding! She was flexible and was able to accommodate my crazy schedule with time to meet my girls and see if their personalities were a good match. (Side note: they totally were.) I loved the details and the report card she left for me about the goings on of their adventures together. Thank you, Heather, for making my girls’ first experience amazing! 🩷

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Lindsay S.
Drop-In Visits
5.0 out of 5 stars

She was absolutely amazing! There was an issue with the apps location which gave a different one than our home! She was so adaptable and still hung out with my dog for the entire time! Cannot thank her enough

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Jaydin G.
Drop-In Visits
5.0 out of 5 stars

So responsive and timely! We booked late and Awnna made it work!her updates were so helpful and reassuring!

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Abby T.
Drop-In Visits
5.0 out of 5 stars

Peyton was awesome with our puppy Luna! She let us know what they did, kept us updated, and even took her for a walk during our drop in visit. Would recommend and have her come again!

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Jenna G.
Drop-In Visits
5.0 out of 5 stars

Kelsey was very timely and had great communication. She is very experienced with animals and exceed my expectations watching my two dogs. I would highly recommend her!

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Theresa B.
Drop-In Visits
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Book with peace of mind

  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

Why Choose Rover?

  • Cashless payments

    Book and pay through Rover’s secured platform—no cash or checks required.

  • Reservation protection

    It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

Meet local sitters who will treat your dogs like family

  1. 1. Search

    Browse profiles of sitters near you who offer dog sitting
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform

Sitters in Windsor average 7
repeat dog sitting clients

FAQs for Drop-In Visits - Windsor

Frequently asked questions about Rover

The average cost for Dog Sitting in Windsor on Rover is $19.26 per visit (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Dog Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Sitting. For more information on service fees, click here .

As of July 2026, there are 1,459 sitters on Rover offering Dog Sitting across Windsor. Enter your ZIP code to see which available sitters are closest to your home.

A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.

Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Windsor stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.

Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.

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 Windsor 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 short introductory meeting between you, your dog, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter 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. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

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 Windsor 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 Windsor. On Rover:

  • 91% of sitters can help with special care needs
  • 95% 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 calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

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

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