Pet Sitting Windsor
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.
Over 179 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.
“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.”
“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.”
“Allison has been very pleasant and professional to work with. She communicates well and always leaves a detailed report on how the visit went. I have a new 5 month old German Shepherd rescue dog (who is still recovering from surgery). She can be a handful at times. It’s been such a relief knowing that she’s in capable hands with Allison. I highly recommend her for dog walking and/or drop in visits.”
“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!!”
“Jen is incredible! She is so calm and takes my two border collies in stride! She walks them, plays with them, feeds them and is always very dependable 💖 I would recommend her to anyone in the Madison area! It’s a sense of relief when I have her booked.”
“Susan and Molly are always fantastic! This most recent time, they cared for my 3 cats for almost a full week. I work from home, so I was nervous about being away for so long. However, each day Susan and Molly sent me pictures and updates, which allowed me to fully enjoy vacation rather than worry that the cats weren't getting enough attention or care. My kitties really love them!”
“Needed a couple drop-ins on short notice so I contacted Hailey and she got back to me right away. We set up a meet and great for that evening and she was right on time. All 3 dogs just loved her at first sight! After they got their attention we went over all the details of food, water, etc. She was on time to appointments and sent pics during visit. Hailey has great communication and I will definitely use her again.”
“Rachael took a ton of amazing pictures of my 3 cats while I was away, and I really appreciated that! It made me feel good to see that they were all doing well. All 3 of my cats seemed to like her too which is awesome!”
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!
“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!”
“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!”
“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.”
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!
About: I have had experience watching dogs since I was 12. My neighbors often have me walk their dogs when they are unable, and about a year ago I started watching my family and friend’s dogs when they are out of town. I currently work part-time and I don’t have school during the summer so I am free most week days. I am also available on various weekends depending on my other job’s schedule. I create a safe environment in client’s homes by ensuring the dog has nothing dangerous within reach. Keeping a clean and safe space helps the both the dog and owner feel more at ease.
The median cost per visit for pet sitting in Windsor is $20
Pet parents share their Rover experiences - Windsor
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! 🩷
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!
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!!
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.
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.
How Rover works
1. Search
Browse profiles of sitters near you who offer pet sitting
2. Meet & Greet
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
Popular requests near you
Select a filter and find qualifying Windsor sitters!Sitters in Windsor average 6 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 July 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 July 2026, there are 1,522 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
- 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.
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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