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Top rated Windsor house sitters
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Ryan and Shannon took great care of both my dogs. They were very responsible and kept me posted on everything while I was away. House looked as perfect as I left it, too! Many thanks to you both. Looking forward to having you sit again when I’m away.”
About: I've been lucky enough to have a dog in my life since I was 8 years old, and now I'm 20! My dog is 13 years old, and caring for her has taught me so much about patience and responsibility. She takes multiple medications, so I'm very comfortable with medication schedules and making sure pets receive the care they need on time. I've also looked after other pets for family and friends like my friend's 3 cats, Rocky, Pepper and Sage, during school breaks, and the cutest dog in the world, Abby. These experiences helped me become confident caring for pets with different personalities, routines, and needs!! I truly love spending time with animals, cuddling, playing, keeping them company, or just making sure they stay active and happy. I'm an outdoorsy person who enjoys hiking and walking, so I'd be happy to take your dog on walks and adventures if needed. I'm reliable, attentive, and comfortable with feeding and following special instructions to ensure your pet feels safe, loved, and well cared for! I’m planning to have an internship, so I’ll be working full days but will be able to periodically check in on your animals!! I love to play and spend time with them, and you can trust they’re in great hands! My puppy is 13 years old, and is on many medications, has specific feeding times and diet, but she still loves to play and go on walks! I’m super organized and take very good care of her.

“Emma took excellent care of our two dogs while we away. She followed all instructions and was very responsive both before and during our trip. We came home to two happy pups! I would definitely book Emma again the next time we need an overnight sitter.”

“Kelly was a great communicator. Our dogs loved getting to know her. She was responsible with giving one of our dogs medication and following our routine. We wil be using her again for dog sitting needs.”

“It was our first time using Rita and she was amazing with our energetic pup! She treated her like her own and kept us updated with texts and pics the whole time. We came home to a happy, tired dog and couldn’t ask for more!”

“Ruth was amazing! She stayed at our house for 5 days and took such great care of our Charlie boy. She even came during her lunch breaks to take him out. She was honestly the best ! And she sent me pictures everyday which helped me be less anxious. Highly recommend and will be a repeat client 🩷”

“Mirella did a great job with our dog and cat! She was careful to follow their routines and to keep up with frequent walks and clearing some ice/snow from our walk! Highly recommend”

“Sharyn went 1000% above and beyond for our Jace ! She was patient, kind, understanding and empathetic with our scarred little pup. I was very nervous leaving him at home while we went on vacation but Sharyn eased my mind and treated jace with an overwhelming amount of care. I cant say enough amazing things about her !”

“Boryana is an extremely professional and reliable pet sitter. She has excellent communication skills, is very attentive to details, and did an outstanding job taking care of my cats. I felt completely at ease knowing they were in such good hands. I would highly recommend her to anyone looking for high-quality pet sitting services!”


“This was our second time using Karren -- this time we had her stay with our pup in our home for 2 nights. Karren was very caring with our dog during thunderstorms and also was very helpful with making sure our home was secure during it. We appreciate her partnership!”

“Giana was such a great help to us when we had an impromptu over night trip. She was very communicative and sent so many pictures of our Shiloh! I would absolutely recommend booking with her and I can guarantee your pet will be happy too!”

About: I have 6 pets at home- 3 dogs and 3 cats. This can be a lot of work, especially considering some of them need more attention than others. This includes a deaf dog, a senior cat with health issues, and other animals that have special needs that need to be met every single day. Caring for animals truly requires a lot of time, patience, and kindness. These are qualities I know I possess and can provide to your animals! Currently, I have a lot of time on my hands. I work a part time job in the afternoon and evenings, and can come pet sit almost any time throughout the week. Though I will be a full time student again in the fall, I still have more than enough opportunities and time for your pets! Having experience in pet sitting I always leave my clients home knowing I did exactly what they asked from me. Whether you need your dogs poop bag in a specific trash bin, or you want me to make sure all your doors are locked before you leave- I will make sure to have it done. I know leaving your pets with someone you don’t know can be a little stressful, so I want to take away from that stress as much as possible. If you have me as a pet sitter, know you can trust me with your fur babies and I will always be leaving your house with every single one of their (and your) needs met.
“Ryan was great! She stayed with our "pups" (as she cutely called them) for almost a week. Right from the start she sent texts, photos, and a sense that all was under control. Meeting her before the stay both her experience as a student working towards going to vet school and as a horse owner sealed the deal. We'd happily use her again.”

“Alexis was a great sitter for our two big pups! She spent a lot of time with them and sent daily photos! She followed all the feeding and sleeping instructions and we came back to a clean house! She even left treats and cupcakes for us to give the pups on our return!”

About: I’m a responsible local college student offering dog walking, drop-ins, and basic pet care. I’m newer to Rover, but I’m reliable, patient, and careful about following each owner’s instructions. I’m available every day on a flexible summer schedule for dog walking, drop-ins, and basic pet care. I’ll keep my availability updated and am happy to discuss your pet’s routine ahead of time to make sure I can provide reliable, consistent care. I take safety and trust seriously and will follow each owner’s instructions carefully. During walks, drop-ins, or stays, I’ll make sure pets have fresh water, proper leash or harness use, potty breaks, and a calm environment. I’m happy to send updates and photos so owners know their pets are doing well.
“Ashley took excellent care of my greyhound and cat! My dog is older and has some special care requirements (supplements, diapers, anxiety) and Ashley had no issues managing it.”

“Vee was very attentive to our cat, Chaos. She took the time to come meet us before her stay, and she followed all of our instructions to the letter, especially for his medication. She kept us updated with information and pictures, and clearly enjoyed taking care of Chaos. We hope to have Vee cat sit for us again!”

Windsor pet parents share their Rover experiences
Elizabeth was amazing right from the meet and greet! We knew Storm was in great hands from the start. We didn’t have to worry about her once while we were away, and that peace of mind was priceless. Elizabeth kept us updated and took great care of Storm. We’ve already booked her for our next trip and highly recommend her to anyone looking for a reliable and caring pet sitter!

Ryan and Shannon took care of our senior dog for a week in our home. They were highly professional and loving companions for her, taking her for walks and handling her medication skillfully. They kept in touch with us on a regular schedule. We recommend them highly. Great to have them both with her.
Sarah was great! She did everything I asked her to in regards to taking care of my pups. She even watered my flowers and got my mail. The house was in great shape when we got home and the dogs were fine and happy. Sarah said she enjoyed the dogs company and would miss them which warmed my heart. We will use her again.

How Rover works

1. Search
Read verified reviews and choose a house sitter who’s a great match for you and your pets
2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
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 house sitting in Windsor is $60
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 house 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 3 repeat house sitting clients
House Sitting FAQs
Frequently asked questions about Rover
House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Windsor on Rover as of Jun 2026 was about $60 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.
As of Jun 2026, there are 1,522 house sitters in Windsor. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.
Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 84% of Windsor house sitters respond in under an hour.
House sitters in Windsor have an average of 15 years of experience. House sitters with repeat customers have an average of 3 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Windsor.
Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Windsor house sitters are great for:
- Dogs who’d prefer to stay on their home turf
- Cats and caged pets
- Pet parents on a tight schedule
- Keeping an eye on your home and plants while you’re away
Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house 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 house 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 house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.



