Pet Sitting 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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Over 186
pet parents in Windsor have booked pet sitting

Windsor, Find top rated pet 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: Jen D.
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Jen D.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
336 reviews
74 repeat clients
15 years of experience
Berkley Oaks, Madison, WI, 53704

Another great visit from Jen. Love having her come over and take care of my dogs because I know they’re gonna be well careful while I’m gone.

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Julie M.
Sitter Profile Image: Heather S.
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Heather S.
Star Sitter
from
$23
per visit
5.0 out of 5 stars
41 reviews
7 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: Karen C.
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Karen C.
from
$15
per visit
5.0 out of 5 stars
6 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: Tonisha A.
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Tonisha A.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
56 reviews
14 repeat clients
30 years of experience
Sun Prairie, WI, 53590

Tonisha took great care of our kitties while we were on vacation! We really appreciated the photos and videos she sent every day. We would love to have her sit for us again in the future!

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Kristin R.
Sitter Profile Image: Mira D.
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Mira D.
from
$17
per visit
5.0 out of 5 stars
4 reviews
2 repeat clients
10 years of experience
Waunakee, WI, 53597

Great sitter - will book again!

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John G.
Sitter Profile Image: Anna S.
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Anna S.
from
$19
per visit
5.0 out of 5 stars
5 reviews
2 repeat clients
16 years of experience
Sun Prairie, WI, 53590

Anna was wonderful with our girl, who warmed up to her very quickly. She was friendly and efficient; basically a joy to work with. I'd give her more stars if I could.

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Jennifer N.
Sitter Profile Image: Darshani L.
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Darshani L.
from
$13
per visit
1 repeat client
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: Taryn E.
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Taryn E.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
29 reviews
13 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: Hailey M.
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Hailey M.
Star Sitter
from
$23
per visit
5.0 out of 5 stars
37 reviews
7 repeat clients
10 years of experience
Madison, WI, 53704

Hailey was so great! Took such great care of my cat while I was away, couldn’t ask for better help. Very responsive and flexible with schedule that needed changing a few times. She sent pictures every drop-in and kept me updated! Definitely recommend Hailey to watch after your pets also.

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Trevor S.
Sitter Profile Image: Emily L.
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Emily L.
from
$20
per visit
5.0 out of 5 stars
27 reviews
10 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: 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: Jackie G.
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Jackie G.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
66 reviews
18 repeat clients
20 years of experience
Madison, WI, 53718

Jackie is awesome! She did an amazing job taking care of our girl while we were away and then some! She is friendly, communicative, flexible and considerate. We would love to have her back again and happily recommend her to others!

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Alicia W.
Sitter Profile Image: Allison B.
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Allison B.
from
$20
per visit
5.0 out of 5 stars
7 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: TAYLOR P.
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TAYLOR P.
Star Sitter
from
$24
per visit
5.0 out of 5 stars
42 reviews
15 repeat clients
15 years of experience
Madison, WI, 53704

Taylor did a great job checking in on my kitty while we were away. She did exactly what I asked of her and felt my cat and home were in good hands.

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

Michel is awesome! She takes great care of my kitties and they love her. I feel really comfortable going out of town knowing that she will be taking care of my pets. She sends me such great photos of them also. Would highly recommend Michel!

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Anna H.
Sitter Profile Image: Mary W.
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Mary W.
from
$14
per visit
5.0 out of 5 stars
9 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: Katelyn R.
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Katelyn R.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
48 reviews
16 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: Toni S.
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Toni S.
Star Sitter
from
$12
per visit
4.9 out of 5 stars
56 reviews
24 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: 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: Donovan S.
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Donovan S.
from
$13
per visit
18 years of experience
Sun Prairie, WI, 53590

About: I've had dogs every year of my life. Moved around the country with them, and taken care of them like family since before I could walk. I've taken care of all ages. I'm currently working part time to help put me through college, so I have plenty of time most days to come in and take care of your dogs. I know how to make sure your dogs is safe and taken care of, and will follow any instructions about how you specifically want things done. Everyone does things differently, and I want to try and keep their habits as similar to normal as possible.

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The median cost per visit for pet sitting in Windsor is $20

Pet parents share their Rover experiences - Windsor

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5.0 out of 5 stars

Brandy is fantastic. We've worked with her multiple times, and she is always a accommodating and a great communicator. She took our booking rather last minute this time, and it's such a relief knowing our fur babies are in great hands. Thank you, Brandy!

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

Heather is absolutely amazing! She was so through during our meet and greet. She was fantastic with our fur babies, gave amazing updates while we were away. We got so many photos of them. She really helped to put our anxiety at easy of leaving our senior cats for a week. I would highly recommend Heather to anyone, she is a fantastic pet sitter.

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Kiara Z.
Drop-In Visits
5.0 out of 5 stars

Taryn did a great job with my 4 cats. She was punctual, attentive, and friendly with them. I would definitely rebook again.

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Joleen W.
Drop-In Visits
5.0 out of 5 stars

Karen did a excellent job caring for my cats! She followed all requests in a timely fashion. We arrived home to happy cats.

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Mary Jo W.
Drop-In Visits
5.0 out of 5 stars

Della did great with my cat all week and was willing to jump right in with short notice. I enjoyed the daily updates and her helpful nature.

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Bryant V.
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

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

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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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 pets like family

  1. 1. Search

    Browse profiles of sitters near you who offer pet 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

Popular requests for pet sitting - Windsor

Select a filter and find qualifying sitters offering pet sitting.

Sitters in Windsor average 7
repeat pet sitting clients

FAQs for Drop-In Visits - Windsor

Frequently asked questions about Rover

The average cost for Pet Sitting in Windsor on Rover is $21.09 per visit (as of September 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Pet 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 Pet Sitting. For more information on service fees, click here .

As of September 2026, there are 1,460 sitters on Rover offering Pet 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.

If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.

The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.

Many pet parents provide a spare key or arrange a lockbox. You can also exchange keys during the Meet & Greet and show your walker how to use digital fobs or personalized codes. It helps to arrange access to your home, from spare keys to concierge introductions, before pet care begins.

If you live in an apartment or condo, don’t forget to discuss details like buzzer access, codes, or elevator etiquette. These details can help a pet sitter feel more comfortable going in and out of your building.

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.

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
  • 96% can help with giving oral medications or injections
  • 95% 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.

A Meet & Greet is a short introductory meeting between you, your pet, 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.

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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