Pet Sitting in Windsor

Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Top rated Windsor pet 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: Della H.
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Della H.
from
$15
per visit
5.0 out of 5 stars
6 reviews
1 repeat client
3 years of experience
Windsor, WI, 53598

Della did a fantastic job of taking care of our cat, spending time with him and looking after his needs. She was reliable and a great communicator.

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Virginia F.
Sitter Profile Image: Heather S.
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Heather S.
Star Sitter
from
$23
per visit
5.0 out of 5 stars
30 reviews
4 repeat clients
25 years of experience
Windsor, WI, 53598

We couldn't have asked for a better sitter for our two cats Mochi & Frankie! Heather truly went above and beyond, giving us total peace of mind while we were away. She didn't just handle the basics, Heather took the time to really bond with our cats, sent the best photo updates, and even got my shy Covid kitty to play and come out. It’s clear Heather genuinely loves animals. We’ll definitely be booking again!" We appreciated all the updates and photos.

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Jullie B.
Sitter Profile Image: Allison A.
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Allison A.
from
$10
per visit
5.0 out of 5 stars
129 reviews
31 repeat clients
25 years of experience
DeForest, WI, 53532

Allison was so great with our dogs. Very routine oriented which provides consistency and a schedule that makes them comfortable. Will definitely use her again!

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Jessica C.
Sitter Profile Image: Taryn E.
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Taryn E.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
26 reviews
13 repeat clients
4 years of experience
Windsor, WI, 53598

Taryn was excellent. It was our first time using Rover for drop-in visits. Our cats loved Taryn and she took great care of them. She was a great communicator and went above and beyond. We will definitely use Rover again because of our wonderful experience with Taryn.

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Missy M.
Sitter Profile Image: Tiana B.
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Tiana B.
from
$20
per visit
5.0 out of 5 stars
30 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: Jen D.
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Jen D.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
275 reviews
62 repeat clients
15 years of experience
Berkley Oaks, Madison, WI, 53704

Jen was excellent! She was always on time and provided us detailed feedback. We enjoyed the numerous photos she took! Jen went the extra mile to get to get to know our dog:) She is kind, compassionate, and trustworthy! We would definitely book her again!

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Jody T.
Sitter Profile Image: Katelyn C.
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Katelyn C.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
39 reviews
12 repeat clients
10 years of experience
Sun Prairie, WI, 53590

Katelyn took great care of my cat and made sure she got lots of playtime and attention. She was also able to be flexible when our travel plans changed last minute.

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Hannah P.
Sitter Profile Image: Autumn H.
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Autumn H.
from
$18
per visit
5.0 out of 5 stars
17 reviews
7 repeat clients
10 years of experience
Sun Prairie, WI, 53590

Autumn did a great job with our 2 cats and even got our shy tuxedo to play and ask for chin scratches.

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Tim C.
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

Susan and Molly are wonderful! We love all of the photos they send of our kitties playing with them. We will definitely continue having Susan and Molly as our pet sitters. They even took care of our tortoise while we were away. :)

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Kari E.
Sitter Profile Image: Karen C.
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Karen C.
from
$15
per visit
5.0 out of 5 stars
4 reviews
1 repeat client
35 years of experience
Windsor, WI, 53598

Karen was fantastic with our cats! Treated them wonderfully and sent the best update pictures. Will for sure be looking into her again next time!

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Samantha D.
Sitter Profile Image: Milan R.
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Milan R.
from
$15
per visit
10 years of experience
DeForest, WI, 53532

About: Hi! My name is Milan, and I am a dependable, caring, and responsible pet lover. I have experience caring for dogs, cats, and other pets for family, friends, and neighbors. I am comfortable feeding, walking, playing with pets, administering basic care, and following specific instructions to keep your pet happy and safe. As a CNA, I am detail-oriented, trustworthy, and used to providing compassionate care. I understand how important pets are to their families and will treat your pets like my own while you’re away. I have a very flexible schedule and am available most days, including weekdays, evenings, weekends, and holidays. Pet care fits easily into my daily routine, allowing me to provide plenty of attention, playtime, walks, feeding, and companionship. I am happy to accommodate different schedules and can often accept last-minute bookings when needed. Your pet’s safety, comfort, and happiness are my top priorities. I carefully follow all instructions regarding feeding, medications, exercise, and routines. I provide regular updates and photos so you can feel confident while you’re away. Whether caring for pets in your home or during walks and drop-in visits, I will treat your pet like family and ensure they receive loving, reliable care at all times.

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: Darshani L.
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Darshani L.
from
$13
per visit
10 years of experience
Windsor, WI, 53598

About: I’ve grown with big dogs my whole life and I have my fair share of personal experience with smaller ones as well. Additionally, I worked at Paradise Paws (doggy daycare) as a dog handler for about a year. I am very familiar with all the different breeds and personality types, even puppies! I have a very flexible schedule. I do online school and don’t have another job, so I have lots of opportunity during the day to hang out with your dogs! I will care for your dogs depending on your environment and the rules you have set for me. I will respect your environment and that of the dog, while ensuring they receive lots of fun and attention!

Sitter Profile Image: Michel P.
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Michel P.
from
$23
per visit
5.0 out of 5 stars
79 reviews
31 repeat clients
30 years of experience
Sun Prairie, WI, 53590

Michel is the best! She takes such good care of our kitties and sends the best photos. We have booked her multiple times and will continue to do so. 1000 percent recommend!

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Anna H.
Sitter Profile Image: Hailey M.
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Hailey M.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
19 reviews
4 repeat clients
10 years of experience
Madison, WI, 53704

Hailey was amazing with my two cats! From the photos she shared, I could tell that they were completely happy and comfortable with her. She sent detailed reports and lots of photos, which gave me peace of mind that the kitties were doing well while I was away. Thank you, Hailey!

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Erma D.
Sitter Profile Image: Toni S.
Verified Background Check
Toni S.
from
$12
per visit
4.9 out of 5 stars
55 reviews
23 repeat clients
30 years of experience
DeForest, WI, 53532

Toni went above and beyond! Not only did she take superior care of our little cavapoo, Bailey, she brought our garbage cans in from the curb and offered to check in on Bailey one more time if we were running late. Excellent care and service!!

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Amy K.
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: Alyssa T.
Verified Enhanced Background Check
Alyssa T.
from
$20
per visit
5.0 out of 5 stars
80 reviews
19 repeat clients
10 years of experience
Sun prairie, WI, 53590

Alyssa watched our three pups for two days with four visits and did an outstanding job! Highly recommend her!!

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Michael P.
Sitter Profile Image: Samantha S.
Verified Enhanced Background Check
Samantha S.
Star Sitter
from
$13
per visit
5.0 out of 5 stars
46 reviews
18 repeat clients
25 years of experience
Madison, WI, 53704

Samantha has been so wonderful with my Australian Shepard. She gives amazing updates and always sends multiple picture updates! She is a great and compassionate sitter, Jonee and I appreciate her!

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Tiffanni S.
Sitter Profile Image: Ben G.
Verified Enhanced Background Check
Ben G.
from
$25
per visit
5.0 out of 5 stars
12 reviews
2 repeat clients
35 years of experience
Windsor, WI, 53598

Ben was great with our two dogs - very responsible and friendly and Alvin and Stella enjoyed their walks with him!

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Carol P.
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Over 68
pet parents in Windsor have booked pet sitting

Windsor pet parents share their Rover experiences

1 / 1
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

Kelsey did a fantastic job caring for our cat while we were out of town. We will definitely rebook in the future!

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

Heather did an amazing job. Normally when we return from a trip it takes a day for our fur babies to 'accept' that we are back and 'forgive' us our trespasses. Not this time! They were like 'Oh, you're back. Cool. Where's Heather? Can I get a scratch?" She takes the time to play with them and earnestly cares about them. Her reports are thorough and emotive. She also has taken beautiful photos. We have already saved many and plan on creating an album. Heather, thank you! We can't thank you enough. Jennifer and Aaron

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Aaron H.
Drop-In Visits
5.0 out of 5 stars

Awnna took great care of our cats! She administered meds to one of our cats that required 2 visits per day. She fed and played with them and made sure water bowls were filled and litter boxes scooped. Awnna did a wonderful job and we would definitely have her take care of our kitties again!

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Deborah E.
Drop-In Visits
5.0 out of 5 stars

Taryn does a great job of caring for George while we’re away. As long as she’s available, we’ll welcome her back anytime!

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

This was a very long time for us to be away. We have now only used Brandy to take care of our very precious Nemo. He is so special and we love him and worry a lot about leaving him. It was very hard as this time we would be out of the country. But he was in such good hands with Brandy that we did not worry at all. He likes her and was interacting and playful which was a worry as he tends to like his space but requires a lot of attention from his own people. And he can get lonely. We are grateful and thankful and all the things that we have Brandy. She better plan on being around until the end of time!!

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Julie M.
Drop-In Visits
5.0 out of 5 stars

We've used Karen twice to check in twice a day on our two cats, and she has been wonderful both times. Very professional, very good with the boys (one who wants all the attention and one who wants none ever). Kept us updated and well informed, we will absolutely be using her again. This last time was a pretty last minute booking and she was able to work with us.

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Samantha D.
Drop-In Visits
5.0 out of 5 stars

Kirstyn is fantastic; our boys love her and she takes great care of them. Communication with her is easy. She sends pictures and details of each check-in.

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Missy M.
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
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Find pet care near you

How Rover works

  1. 1. Search

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

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your pets 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 pet 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 pet 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.

Sitters in Windsor average 8
repeat pet sitting clients

Pet Sitting FAQs

Frequently asked questions about Rover

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

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

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

As of Jun 2026, there are 322 pet sitters in Windsor. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass a background check for you and your pet’s safety.

Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, 85% of Windsor pet sitters respond in under an hour.

Pet sitters with repeat customers have an average of 8 repeat clients. Experience can vary from pet sitter to pet 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 pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:

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

There are 322 pet sitters in Windsor on Rover, so you’re sure to find the perfect match for your pet! We understand that each pet is unique and may require specific instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, all pet sitters on Rover have been background checked and screened for you and your pet’s safety.

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

Note: If your pet 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 pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.