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. Ace G.
“Ace is our go to person for our very anxious yet adorable Beagle. Our pup is so well taken care of by Ace. We have no worries when they are on the job!”


2. Brendon P.

“I can not say enough good things about Brendon. We had a request to bring our dog to our wedding which Brendon was gracious enough to do. He made sure to do two visits beforehand to ensure everything went smoothly. He was timely, responsive, and sent updates about our dog. Our dog was well taken care of and in good hands. I would defiantly use him again for house sitting.”


3. Theresa C.

“This a second review and want to acknowledge what lovely care Theresa took of my 2 dogs. They were extremely happy when we came home and I know they were well cared for in our absence.”


4. Julia B.

“Julia sat for my dog for two nights. She was a wonderful communicator (even before her stay) and provided updates throughout with pictures. I have a high energy dog and she made sure he got plenty of walks and play time. I felt at ease being away and knowing that my dog was in good hands. My home was left exactly as it was found. I will be using Julia again and would highly recommend!”


5. Angela W.

“This was our second time trusting Angela with our Shelby and she was amazing. Her daily updates were to comforting and it was clear she totally "gets" Shelby and genuinely cares about her. She was able to stay at the house and not leave Shelby alone for long periods of time which is exactly what Shelby needed. When we got back, she had gone above and beyond and stripped the bed and washed a blanket. Finally, and most importantly, she's just a delight. Her upbeat manner is a joy and added to the fun of getting daily updates. We will definitely hire Angela again.”


6. Hunter F.

“Hunter was really accommodating when we got sick while trying to schedule our meet & greet for a last minute trip. She did great with the dogs & allowed us a stress free weekend away!”


7. Karina S.


“Karina was awesome. The family member who was going to stay with our dog came down with Covid 24 hours before our trip. Karina was responsive, accommodating and took great care of our elderly dog. We highly recommend her!”


8. Marisa M.

“Wish we could give ten stars! Marisa was so attentive to our dog with special needs and looked after everything at the house. This was the first time in three years we were able to go away without worrying. Such a blessing!”


9. Jesse R.
“I can't thank Jesse enough for the amazing care he provided to my dog over the weekend! From the moment I met Jesse, I felt completely at ease knowing my couch hippo would be in great hands. They kept me updated with pictures and messages, which reassured me that my dog was happy and comfortable. Jesse went above and beyond to ensure my dog’s needs were met, from playtime to walks and even a cozy nap on the couch. My dog came home relaxed and content, which is always a sign of a great sitter. I highly recommend him to anyone looking for a trustworthy and caring sitter. I’ll definitely be reaching out again next time!”


10. Felicia G.
About: I’m a pet enthusiast who makes friends with all four legged buddies I come across! I’ve gotten along with every animal I meet and will be not only a dog/cat watcher but a companion while you’re away. I will ensure the best comfort of your pet and treat them as if they’re my own. Want someone who gives your pet undivided attention? I’m your gal! Your pet will never feel alone while with me. I live in a friendly neighborhood where we can go for many walks and my yard is also the perfect size for any games your little friend might enjoy. When your pet is with me it will be a home away from home with for them, guaranteed. I’m currently self employed, owning my own dog cookie business so I have unlimited amounts of time for furry friends everyday to help ease your worries during your work days and vacations! I care for every animal as if they are my own fur baby! I have years of experience in multiple fields of the pet industry. I am certified in pet CPR and first aid so rest assured your pet will be safe with me at all times. I have experience in dog training and grooming as well.


11. Tara N.

“Tara sent beautiful photos of my girl, and it is obvious just how happy she is. Tara is knowledgeable about dog care, and identified a potential ear infection right away, and our vet told me she did all the right things and it cleared up the next day. I completely trust her with the care of my dog and my home and will definitely book with Tara again.”


12. Jonathan H.
About: I grew up with as many as 5 cats and two dogs at a time. I am familiar with caring for most pets including rodents and fish. I work from home so taking a break to walk or feed pets is not an issue. There is even some extra time to give them some attention too! My dog has free roaming permission in the backyard and we also have a cage for large dogs available. For visiting dogs we walk them on a leash since they are not familiar with the area.




13. Cristin B.
About: I enjoy the outdoors and taking a walk. Your dog will have lots of play time, as well as fun, treats, food and water. I just like having a dog around to keep each other company so they are not home alone for long time period, you know getting into mischief we can do that together and have more fun haha. I currently do not have any dogs but will get one when the time is right. I have enjoyed and attended dog shows showing for obedience and agility(Dalmatians). I also attended and passed the canine good citizenship test with my first dog. My second dog was adopted and we did agility and was a lot of fun. A dog is a companion in which you meet other dog friendly people. I'm currently working full time but would have time to care for your fur kid/s before and after work, get mail, water plants, check house. I do not have a fenced yard so would take your fur kids out on a leash at your home or if fenced and you chose for them to be loose at your home.


14. Arianna G.
“Hey my name is Renee I’ve known arianna for multiple years and I can say I trust her with all my heart. She’s very kind and patience and always will to try/ learn new things. Arianna is great with animals of all sizes. I know this from experience since she is one of the few people I trust to watch my fur babies when I’m out of town.”


15. Tyler G.
“Let me start by saying that both my fur family and my human family love when Tyler comes over. We have had him care for our pets on multiple occasions, sometimes just coming for an hour in the afternoon when we are gone all day, sometimes staying in our home for a several days at a time. Our dog is a huge fan of the endless belly rubs, and our cat loves the quiet quality time, on the sofa, next to Tyler. I take comfort in knowing that Tyler reads and follows the instructions I leave, and always asks questions when he's not sure of something. As long as he is around, we know our pets are happy, plants are watered, and home is safe.”


16. Chris D.

“Chris took such good care of our dogs. During our initial meeting, he asked follow up questions so that he clearly understood the feeding routine. He asked other questions that let us know he read the profile ahead of time. His daily updates provided excellent information and great photos. We are so happy for what Chris did. We highly recommend him. We will always check his availability when we are going out of town.”


17. Stacey G.

“Stacey was wonderful! She was so easy to communicate with ahead of watching our dog and was also super self sufficient around our house. There was a bad storm when she was scheduled to watch our dog and we live in a pretty remote area and she had zero complaints. She was fantastic all around!”


18. Katherine C.

“Katherine made us feel at ease leaving our dog for the weekend. She sent lots of pictures and check-ins which we really appreciated, and highly recommend her. After a long weekend we came back to a very happy boy.”


19. Hadley L.
About: Hi, I am 34 and an animal lover. I have a full time job that is a flexible and I love being outside whenever I can be. I have one rescue dog and one rescue cat that get along great and love other animals. This is a side job/passion project for me that I have been doing for years and don’t plan on stopping. I have 5 sometimes 6 dogs I walk each week and would love to add your pup to my schedule. I am also comfortable with cats and other animals as well. I respond quickly and would love to talk about how I can help you out. Thanks! I am currently working from home and am able to make my own schedule. I love filling that time with dog walks and home visits. I am located in New Hartford and love walking around my neighborhood, there is also a great hiking trail within a few miles of my house that I frequent.


20. Danyelle G.

“Danyelle was absolutely superb and loving with my dog Juno and my parents dog Nemo (and very patient with some changes that kept coming up on our end).”
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 Apr 2025 was about $55 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 Apr 2025, there are 438 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, 88% of Winchester house sitters respond in under an hour.
House sitters in Winchester have an average of 16 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.
