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

Taryn was kind and very patient with my older, unsure little dog. Everyday Taryn took her time to get to know him. She was friendly and gentle allowing him to get used to her visits.

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

Allison is fantastic! She had issues with our garage door (our fault-not gets!) and she problem solved and told us right away her plan of action. Allison is trustworthy, punctual and professional!

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Mindy H.
Sitter Profile Image: Awnna H.
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Awnna H.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
50 reviews
18 repeat clients
11 years of experience
DeForest, WI, 53532

Awnna was a great sitter, would recommend to anyone and would book again in the future! Thank you so much for taking good care of our dog and making him feel loved while we were away!

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Ashley G.
Sitter Profile Image: Jen D.
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Jen D.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
226 reviews
49 repeat clients
15 years of experience
Berkley Oaks, Madison, WI, 53704

10/10 absolutely so grateful to know our cats were in such good hands when we went out of town for the first time since moving to a new city! I told Jen not to hold back on pictures and she delivered 🤣👌 she is a great photographer!! All jokes aside, we will always book her when she's available! Thanks for taking such good care of our babies!

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Clarissa H.
Sitter Profile Image: Heather S.
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Heather S.
from
$23
per visit
5.0 out of 5 stars
17 reviews
1 repeat client
25 years of experience
Windsor, WI, 53598

About: I've been caring for animals for as long as I can remember. I connect with each animal and get to know what is normal behavior and what isn't so I can quickly identify if anything seems off. You can rest easy knowing you'll be immediately informed if anything seems concerning. And, I'll also provide updates with each visit, including pictures. I am an excellent communicator and very detail-oriented. I ask lots of questions during meet-and-greets to ensure there is no disruption in your pet's usual care and routine. I work from home and have a very flexible work schedule, so I can make frequent visits almost any day of the week. If your pet has health concerns (meds, needs to be fed at specific times, etc) or needs a specific schedule, I can accommodate for that the vast majority of the time. I will always communicate any schedule conflicts before finalizing a booking. Safety and trust are always my top priorities. I approach animals I'm just getting to know on their terms so they can feel safe and secure. I am always sure to leave things in your home exactly how you want them, including cleaning up after myself or any pet messes I find.

Sitter Profile Image: Alissa A.
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Alissa A.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
26 reviews
4 repeat clients
25 years of experience
Windsor, WI, 53598

very experienced and good at relating to our somewhat complicated dog. Gave us a peace of mind that our dog was in good hands.

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Steve L.
Sitter Profile Image: Susan & Molly S.
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Susan & Molly S.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
65 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: Toni S.
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Toni S.
from
$12
per visit
4.9 out of 5 stars
53 reviews
21 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: Katelyn C.
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Katelyn C.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
28 reviews
8 repeat clients
10 years of experience
Sun Prairie, WI, 53590

Katie was very punctual and responsive! She was so kind to my cat, followed all instructions, and my cat looked forward to her visits filled with lots of petting! I would recommend her and have her provide care in the future!

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Lindsey T.
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 helped me take care of my cat when I was indisposed and I am so grateful. I would have had a really hard time with the litter box without her coming in to take care of that. Very friendly and experienced. Highly recommend.

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Lisa H.
Sitter Profile Image: Maria & Bryan P.
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Maria & Bryan P.
from
$15
per visit
5.0 out of 5 stars
3 reviews
1 repeat client
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: Rebecca B.
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Rebecca B.
from
$30
per visit
5.0 out of 5 stars
29 reviews
4 repeat clients
20 years of experience
Deforest, WI, 53532

About: We’ve both grown up with dogs and around a variety of animals. I also had a cat as a young person and cared for cats of roommates. I’ve house-sat and pet-sat from Europe to Florida and back to Wisconsin. No kids, no other pets, we’d love to love & spoil your boo while you’re away. I work full time, typically Mon-Fri 7ish to 4ish. I’m typically home weekends. There is some flexibility with my schedule if I know in advance. I have the potential for half days or additional work from home if your pet needs more frequent attention. We have a fenced in yard with plenty of room for them to roam (supervised). We’re cuddle friendly so pets are allowed on the furniture & bed, but we’ll work with you to maintain their habits and training. They can be left free, crated, or contained to a particular room as needed. Any other questions just ask!

Sitter Profile Image: Meghan B.
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Meghan B.
from
$16
per visit
6 years of experience
DeForest, WI, 53532

About: I was raised around all kinds of dogs and have cared for many pets over the years. Friends, neighbors, and family often rely on me to walk, feed, and watch their dogs. I’m comfortable with different breeds, personalities, and routines, and I always make sure pets feel safe, loved, and well taken care of. I currently have a very open and flexible schedule, so I’m able to provide plenty of time and attention to your pets. I can accommodate weekday or weekend visits and will work around your routine to make sure your pets get consistent care. I care for pets in clients’ homes, which helps them stay comfortable in their familiar environment. I’m gentle, patient, and attentive, and I always follow your instructions closely—whether that’s feeding routines, walks, or medication. Your pet’s safety and comfort are my top priorities.

Sitter Profile Image: Elizabeth K.
Verified Enhanced Background Check
Elizabeth K.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
26 reviews
7 repeat clients
30 years of experience
Brentwood Village, Madison, WI, 53704

Great job with our pup Lottie, follow directions great and spent some quality one on one time with our pup! Recommend!

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Dan T.
Sitter Profile Image: Karen C.
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Karen C.
from
$15
per visit
5.0 out of 5 stars
3 reviews
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: Samantha S.
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Samantha S.
Star Sitter
from
$13
per visit
5.0 out of 5 stars
30 reviews
12 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: 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: Brenda S.
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Brenda S.
from
$20
per visit
4.8 out of 5 stars
28 reviews
8 repeat clients
9 years of experience
Westport, WI, 53597

Brenda took great care of my recently adopted feline, Atticus, when I was suddenly called out of town. I found her punctuality and dependability assuring, and her approach to providing care to a skittish kitty in alignment with mine; when I arrived home, Atticus was in great shape, physically and emotionally. Absolutely recommend her with enthusiasm.

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Amber A.
Sitter Profile Image: Ben G.
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Ben G.
from
$21
per visit
5.0 out of 5 stars
11 reviews
1 repeat client
35 years of experience
Sun Prairie, WI, 53590

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.
Sitter Profile Image: Autumn H.
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Autumn H.
from
$18
per visit
5.0 out of 5 stars
14 reviews
6 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.
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Over 65
pet parents in Windsor have booked pet sitting

Windsor pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Awnna has cared for our cats while we were on 2 separate vacations and she’s done a great job communicating and sending photos. She is promptly responsive to my messages and I can tell my cats love her. She has done a great job!

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Brenda A.
Drop-In Visits
5.0 out of 5 stars

Brandy was fantastic! During the meet and greet, she was very thorough and asked great questions. During her visits, she took great pics of the boys and made sure they got all their meds. Will definitely hire her again!

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

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.
Drop-In Visits
5.0 out of 5 stars

Taryn was wonderful with our kitties! She took the time to come over and meet them and us in advance and make sure she understood what they needed and communicated wonderfully throughout the visit. They were happy campers when we came home after our first visit away. We would definitely use Taryn again.

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Lesley C.
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

Kelsey was great! We left town for a week to visit my parents, and only needed someone to check in on our cats a couple days. Kelsey took great care of our cats, and sent us some pictures too. She also brought in our packages which was appreciated so much! She's great at communication, and overall just so kind. Thanks Kelsey!

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Jackie O.
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

As always, Susan and Molly were fast to respond, reliable, and took great care of our cats. Thank you!

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Heather S.
Drop-In Visits
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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 7
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 Mar 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 Mar 2026, there are 323 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, 84% of Windsor pet sitters respond in under an hour.

Pet sitters in Windsor have an average of 15 years of experience. Pet sitters with repeat customers have an average of 7 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 323 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.