Dog Sitting in Windsor

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

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Top rated Windsor dog sitters

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: Tiana B.
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Tiana B.
from
$20
per visit
5.0 out of 5 stars
31 reviews
12 repeat clients
5 years of experience
DeForest, WI, 53532

Tiana was great! She was timely, communicated well, and was great to work with. She came and let out my dog while I was working and took great care of him!

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Daria D.
Sitter Profile Image: Julia G.
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Julia G.
from
$15
per visit
5.0 out of 5 stars
8 reviews
3 years of experience
Middleton, WI, 53562

Julia was an absolute godsend for us. My dog had quite a few issues while we were out of town, and Julia was amazing. She gave me constant updates, came to check on him regularly outside of what was originally booked, and made sure that my dog was safe and cared for. She helped ease my worries, and I would definitely rebook her, no questions asked. Our cat also loved hanging out with her!

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Galilea B.
Sitter Profile Image: Mallory R.
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Mallory R.
from
$20
per visit
5.0 out of 5 stars
6 reviews
1 repeat client
11 years of experience
Arlington, WI, 53911

About: I have been a dog momma and lover for years. They are my world and I am theirs. Yours will be taken care of at the same level I care for my own! I am sincerely drawn to dogs when I see them. They've got so much love and joy to offer this world, how could you not? I have 3 labs currently and have trained all of my dogs from babies on up. We have almost always maintained a 3 dog household, they get walks everyday so long as the weather permits and plenty of playtime. Rest assured, your pup will be taken care of in the same respect and manner as I care for my own. I work from home so can make time for lunch time appointments if close enough to my home, I work until 5 so can be available in the evenings until 9pm, except for Wednesdays I have volleyball either at 6:30 or 7:30, but can still make appointments work in there. Also around most weekends except for family events here and there and two vacations we take a year. :) I protect them with my life. I love my babies so deeply and am so thankful I work from home so I get to be with them everyday. Yours will be treated no different. Dogs have so much love and joy to offer the world and they only deserve the same in return.

Sitter Profile Image: Blaze D.
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Blaze D.
from
$15
per visit
5.0 out of 5 stars
2 reviews
1 repeat client
15 years of experience
Madison, WI, 53704

About: I’m all of my friends and families first choice to watch their pets when they are out of town. I’ve looked after a variety of breeds of dogs and many cats as well. I’ve always had dogs in my life growing up so I’m very familiar with reading their body language and knowing how to care for them. I work full time but have a lot of flexibility to check on your pet throughout the day and have the opportunity to work remote as well I’ve never a met a pet that didn’t like me. I’m very good at reading dogs body langue and knowing what they need. Cats also like me and I’m good at reading their body language as well

Sitter Profile Image: Leah & Jeremy M.
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Leah & Jeremy M.
from
$28
per visit
5.0 out of 5 stars
35 reviews
19 repeat clients
20 years of experience
Waunakee, WI, 53597

Leah did a great job checking in on my cats while we were away. She was communicative, super nice, and followed through with what we asked. She sent lots of pictures of our cats when she checked in on them. When we got home, nothing was out of place and our cats had a clean litter box plus plenty of food and water. I definitely plan on booking Leah again in the future.

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Miriam M.
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: Carley T.
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Carley T.
from
$19
per visit
5.0 out of 5 stars
6 reviews
4 repeat clients
20 years of experience
Westchester Gardens, Madison, WI, 53704

Carly took care of Chester for 1 week as drop-in sitter. My cat looks healthy and handsome as ever. I arrive with a chatty cat greeting me and I get it. I will book Carly again in the future because she not only took care of my cat’s needs (spoiled-prince) but she also respected my place and she is trustworthy and professional.

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Richard N.
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 and her family are by far the BEST sitters I have ever had! They are so sweet, communicative, flexible, and knowledgeable. I hope to use them every time I need extra help with my buddy.

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Coley H.
Sitter Profile Image: Megan T.
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Megan T.
from
$16
per visit
5.0 out of 5 stars
85 reviews
20 repeat clients
12 years of experience
Eken Park, Madison, WI, 53704

Megan always takes great care of our cats! Odin needed additional care and she was so attentive to making sure he got all of his meds and supplements. Thank you!

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Stuard C.
Sitter Profile Image: Lindsey D.
Verified Background Check
Lindsey D.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
49 reviews
18 repeat clients
15 years of experience
Sun Prairie, WI, 53590

Lindsey was professional with excellent communication. She took great care of our Eddie and sent several pictures showing us what a good time he was having ?

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Abigail A.
Sitter Profile Image: Shatoria W.
Verified Background Check
Shatoria W.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
32 reviews
11 repeat clients
10 years of experience
Sun Prairie, WI, 53590

Shatoria was so great with my cats. She is very responsive and a great listener. I had a lot of changes in care instructions, and she handled everything patiently and without any issues. She kept me updated, followed all the details carefully, and made me feel completely at ease while I was away. I could tell my cats were well cared for and comfortable with her. I would absolutely trust her again and highly recommend her to anyone looking for a reliable and attentive pet sitter.

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Duong H.
Sitter Profile Image: Kylie H.
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Kylie H.
from
$15
per visit
5.0 out of 5 stars
6 reviews
8 years of experience
Capitol, Madison, WI, 53703

Kylie did a wonderful job watching my cat mocha while I was out of town for a week. Sent me photos to show mocha was having a fun time during her check ins.

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Jake B.
Sitter Profile Image: Angela N.
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Angela N.
from
$18
per visit
25 years of experience
Sun Prairie, WI, 53590

About: I own two cats, three snakes, and a skink. I do extensive research on all pets to ensure I'm providing excellent care for them. I want to make sure I'm giving all pets the best life even if I'm only taking care of them for a few days. I have experience in giving cats and reptiles medicine orally and via subcutaneous injection. For dogs, I have experience with general care and training. I currently run my own craft business from home. This means I set my own hours and regularly vend at markets in the immediate area. This allows me to fit pet care and visits seamlessly into my schedule. For client home care, I keep food and water at discussed levels. I will also hang out, love, and play with your pet for at least 20 minutes during each visit. For dogs, I will take out on walks. If you pet likes brushes, I'm all for it! If they need meds, I can administer as needed.

Sitter Profile Image: Susan & Molly S.
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Susan & Molly S.
from
$25
per visit
5.0 out of 5 stars
66 reviews
19 repeat clients
30 years of experience
DeForest, WI, 53532

We know our kitties are well taken care of when Molly and Susan come! We can travel and not worry because we know they are getting lots of attention and love.

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Kari E.
Sitter Profile Image: Mackenzie G.
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Mackenzie G.
from
$16
per visit
10 years of experience
DeForest, WI, 53532

About: I’ve had my own dog at home since I was eight and I’ve taken care of countless dogs my entire life. My own dog is getting elderly, so I understand the care and compassionate it takes in order to make sure they’re happy. I love being around dogs so getting to know your pet will be so special to me! I'm currently a college student who is looking to take care of any furry friends in my spare time! I am available over weekends and all weekdays besides Wednesday. 8am-2pm and 8pm-10pm are my best times during the week, and then any time during weekends. I do not currently have any pets living with me at school, however I am extremely used to taking care of my own pets and other family members/friends pets as well.

Sitter Profile Image: Aubrey S.
Verified Enhanced Background Check
Aubrey S.
from
$18
per visit
5.0 out of 5 stars
3 reviews
2 repeat clients
10 years of experience
Cottage Grove, WI, 53527

About: As a 19-year-old sitter, I offer compassionate senior pet care and puppy training experience, ensuring patience, energy, and dedication to keep your pets happy and healthy. Pet care is a joyful part of my daily routine, giving me purpose, structure, and happiness. I love making time for walks, play, and cuddles! I care for pets by following their feeding and exercise routines, providing fresh water, administering medication if needed, offering lots of love, and keeping their environment clean and safe.

Sitter Profile Image: Kristina G.
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Kristina G.
from
$14
per visit
5.0 out of 5 stars
3 reviews
1 repeat client
5 years of experience
Marquette, Madison, WI, 53704

Kristina did a great job watching our cats (and fish), despite the myriad health conditions among the 3 of them. They were all well-cared for and everything was tidy when we came home.

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James W.
Sitter Profile Image: Mary T.
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Mary T.
from
$20
per visit
5.0 out of 5 stars
9 reviews
1 repeat client
4 years of experience
Marquette, Madison, WI, 53703

Mary did an excellent job cat sitting. My cat loves her. She was on time all the time and sent pictures and updates with every visit. She was able to work with my changing schedule and made the process a great experience. Mary is my go-to cat sitter now. Highly recommended!

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John D.
Sitter Profile Image: Michelle F.
Verified Enhanced Background Check
Michelle F.
from
$13
per visit
5.0 out of 5 stars
1 review
10 years of experience
High Crossing, Madison, WI, 53718

About: I am a dog owner looking to spend my free time helping you take care of your loved one! I am kind, gentle, and patient. I also able to adapt to whatever your pet needs. My dog had back surgery years ago, so I have experience with using a harness to assist with walking as well. I'm available anytime during the week or on weekends! Boarding could be an option if you require it, and I would be able to stay overnight if needed. I love going for walks and playing. I live near a small, quiet dog park. I can also come play in your home if that's better, or provide your pet a person to be with if they get lonely.

Sitter Profile Image: Talia W.
Verified Enhanced Background Check
Talia W.
from
$25
per visit
11 years of experience
Madison, WI, 53718

About: I have had cats for more than half of my life and dog-sat for around the same amount of time. I used to dog sit two huskies all the time, had a dog of my own for a short time, and have experience dog sitting for labs as well! I have even taken care of a bearded dragon and snake on multiple occasions. Rover does not list animals other than cats and dogs directly but I am happy to arrange care for another animal as well, including exotic animals, for a fee that can be discussed. I am volunteering at the humane society and am very involved in caring for animals as much as I have time for. I am excited and ready to care for any and all pets that need it and will stick to specific details given. I won't hesitate to ask questions about the care of your pets when I have them to make sure your pet gets the utmost care and love while you're away or busy, and id yoy have plants that need watering, say the word and I'll do that too! I am currently full time in senior year of high-school and volunteering for two hours a week on the weekends, but I graduate in a month and will have all the time in the world to pet sit! I follow every instruction for food, water, walk, and treats and ask questions if I am unsure of something. I tend to stay longer than needed for check in visits just to give pets some company if I have the time. Unless pets are not very social, they will get all kinds of attention, and if they have any anxiety or behavioral differences I will be very careful and act however is best for them. I am very sure to be on time for visits and will be very specific to follow instructions for walking or being taken outside.

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Over 100
pet parents in Windsor have booked dog sitting

Windsor dog parents share their Rover experiences

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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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How Rover works

  1. 1. Search

    Read verified reviews by dog parents like you and choose a sitter who’s a great match for you and your dogs
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your dogs while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

The median cost per night for dog sitting in Windsor is $20

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 dog sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

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

Sitters in Windsor average 6
repeat dog sitting clients

Dog Sitting FAQs

Frequently asked questions about Rover

Dog sitters on Rover are free to set their rates. The median cost to hire a dog sitter in Windsor on Rover as of Jun 2026 was about $20 per night, after factoring in Rover’s service fees. A dog sitter’s rate may also change as you customize your booking to fit your and your dog’s needs.

If you’re searching for a Windsor dog sitter for the first time, visit the dog sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a dog sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 1,471 dog sitters in Windsor. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog sitter near you. As a reminder, dog sitters joining Rover must pass a background check for you and your dog’s safety.

Rover makes it easy to reach out to multiple dog sitters about your booking. Typically, 88% of Windsor dog sitters respond in under an hour.

Dog sitters in Windsor have an average of 16 years of experience. Dog sitters with repeat customers have an average of 6 repeat clients. Experience can vary from dog sitter to dog sitter, but you can view reviews, years of experience, and number of repeat clients when you compare pet sitters in Windsor.

Rover makes it easy to find Windsor dog sitters to provide loving care from their own home. The background-checked, 5-star dog sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog sitting is great for:

  • Dogs of all ages and abilities, including puppies
  • Dog parents looking for a safe, loving alternative to a kennel
  • Dogs who’d love to socialize with their dog sitter’s pets

There are 1,471 dog sitters in Windsor on Rover, so you’re sure to find the perfect match for your dog! In Windsor, 94% of dog sitters offer daily exercise, 96% offer medication administration, and 91% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog sitter near you. As a reminder, dog sitters joining Rover must pass background checks for you and your dog’s safety.

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your dog sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your dog is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your dog sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your dog sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog sitter’s cancellation policy.