House Sitting in Winchester
Find a loving house sitter to watch over your pets and your home.

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Loving house sitters in your neighborhood
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1. Amanda T.

“Amanda is the best! She sent updates daily and I really think Otis would have been happy if I would have stayed away longer! She really knows how to love on him while I’m gone giving me one less thing to worry about!”


2. Alicia R.

“Alicia was fantastic with our dogs. We are always nervous to leave them because one of our dogs is reactive, but Alicia put our minds at ease so we could enjoy our trip. She took great care of our home and communicated with us during our time away. We will always check with her anytime we need a sitter.”


3. Amber B.

“Amber was absolutely wonderful with our two dogs!! She kept us very updated with pictures and messages and even checked in with us on a potential medical issue. They both need oral medication and she was comfortable with that and made sure they had what they needed. We loved having her take care of our pups and felt confident they were safe and happy with her! We’d recommend her to any other families that need someone to love and care for their pets while they’re away!”




4. Angela D.

“Natural animal person! Saved us on short notice. Flexible & understanding!”


5. Bekka D.

“Bekka was so helpful by taking on our pet sitting needs when we were under a tight deadline. She came early to take time to get to know the pets and was snuggling with them in no time. We highly recommend her.”


6. Tessa W.
“Tessa is absolutely wonderful with any kind of animal, I have a dog myself, and she has helped take care of him when I went out of town and made sure I knew he was in the best hands! She also works with animals, and has amazing reviews! I know if you gave Tessa the opportunity, you absolutely would not regret it. She will prove to the company how dedicated, thoughtful, talented, loving and amazing she is!”


7. Courtlin C.

“Courtlin took excellent care of my pups and was adaptable every time I had an unexpected change through the week. Highly recommend her!”


8. Jordan M.
“Jordan was so sweet and took such good care of our babies AND our house. We are so impressed by her and will definitely be using her in the future.”


9. Payton L.

“Payton did an amazing job with our two dogs! She was reliable and communicative. We came home to a clean house and happy pups. We will definitely book her again!”


10. Hayley & Alaina D.

“Hayley is amazing!! My dog is usually a little shy at first with people but he went right up to her and was so comfortable around her. She sent pictures of him while I was gone and gave updates! She is one of the best dog sitters I have used and will definitely use her again!!”


11. Kathryn F.

“Kat was Lexi’s sitter for a week. Everything went great. I had no concerns leaving Lexi with Kat & Lexi can be challenging! She also took care of my house. Peace of mind.”


12. Dina J.

“This was my fourth time using Dina and will not be my last! She's so great with my pets. They clearly LOVE her, even the cats come out of hiding when she shows up. I'm so grateful to have found such a great pet sitter!”


13. Hannah C.
“Hannah has done dog sitting work for me several times in the past. She is absolutely amazing with my dog. Every time I return home, Minnie (my morkie) has been bathed and is happy. Hannah is very responsible and always is on time and keeps me informed of anything I need to know. She is very pleasant and smart and will go far in whatever she chooses to do.”


14. Kristen G.

“Very friendly and responsible. My dogs loved her! She sent lots of photos and updates to reassure me while I was gone. Highly recommend!”


15. Megan D.
“Megan is an absolutely phenomenal human being, caregiver, and animal champion. I've worked personally with Megan through an animal rescue agency where she provided endless love and care for various fosters that came through her home, on top of being the best pet momma to her own crew of animals. Megan was always watchful of her fosters to meet their needs and provide optimal care while in her home, including being diligent about any potential medical or behavioral needs. Megan is well-versed in animal care and has an absolute heart of gold. She's invaluable to the animal word and will provide top-notch care to any animal she encounters. You can't find better!”


16. Chay H.

“Chay stayed with my cat while I was away for a few nights and took amazing care of her. She went above and beyond and even left a cute treat for my cat!! Will definitely rebook with her in the future!”


17. Christan M.

“Both our girls took to her immediately and that is unusual! Trusting your home and fur babies to someone is a leap of faith and I feel like we found an exceptional person to rely on for both.”


18. Samantha D.

“First time having Samantha watch my fur babies. I was on a trip for 5 days and she stayed in my home. She was great! Sent pics, kept me up to date on any issues and the house was spotless when I returned. Highly recommend, but just not during the days I’ll need her:)”




19. Lindsey B.

“It was last minute and she took awesome care of our girl!”


20. Sara W.
“Sara is absolutely amazing with my dog Fizzie! She will love your pets as if they were her own! She is kind hearted and hard working, and I cannot recommend her more for your pet needs!”
How Rover works
1. Search
Read verified reviews and choose a house sitter who’s a great match for you and your pets2. 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 away3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
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.
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 Winchester on Rover as of Mar 2025 was about $40 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 Mar 2025, there are 386 house sitters in Winchester. 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, 91% of Winchester house sitters respond in under an hour.
House sitters in Winchester have an average of 14 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 Winchester.
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. Winchester 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.
