House Sitting in Winchester
Find a loving house sitter to watch over your pets and your home.
Every sitter passes an enhanced background check. Learn about RoverProtect
Top rated Winchester house sitters
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Nina D is the best! We haven't been gone away for two weeks in over 25 years. I never could have left my fur covered babies except for knowing that Nina was keeping them safe & taking such good care of them. She is outstanding - I highly recommend her. Thank you Rover for helping me find her! ❤️”
“Hannah was very compassionate and understanding of my anxiety about leaving my precious tiny senior chihuahua in a hotel in Vegas. She FaceTimed me Before and assured me she was in good hands. She sent me pictures throughout her stay with Coco. Took her for a walk my baby was peacefully sleeping when I got back to the hotel after the concert. I highly recommend trusting Hannah to care for your beloved pet!”
“We found Jill spur of the moment. She was so awesome. Our house was more put together than before we left. Mikey was happy and she communicated so well with us. We will ask her to dog sit again soon.”
“Sierra was house sitting our Belgian malinois Ayva. She said right the way that she doesn't have an experience with this type of breed yet. We explained all the details and directions to take while she was here with our dog. It was easy stay with no issues. She sent pictures to us daily to make sure that we know our dog is fine. House was clean as well, which was very important.”
“Megan took care of our special needs Dane for several days and did a fantastic job! With severe separation anxiety, he can be a handful at times, but he seemed to great with her. We would definitely use her again in the future!”
“Yolanda was great. She sent a lot of photos and updates during her stay with my frenchie girls. They are both rescues and have some quirks. Yolanda was very patient and understanding. She not only did a great job aith the girls, but aslo kept my house nice and was respectful of my property. Wpuld 10/10 hire again.”
About: I have taken care of dogs for at least five years. I have had dogs of my own pretty much since the day I was born! With that, means I’ve taken care of dogs from puppies, to old folks! I work part time, I’m off every day at 12 and free after that! For over night care they would only be alone for about 4/5 hours while at work! My front yard is partially fenced with a dog restraint so they can still venture in the grass, my back yard is fully walled in! And if your dogs love water we have a pool!
“Deanna was great! She responded every time we texted her, contacted us when necessary and took very good care of our dogs and our home. It was nice to come home to happy dogs and a clean house after 2 weeks away.”
“We had Kris stay at our home last weekend and watch our pup Dilly. We were extremely impressed with her care for Dilly and thankful that she could be with her overnight. She kept in touch with me over the weekend and had a good stay. We will absolutely be happy to have Kris in our home again and trust her immensely with Dilly. It's great to be able to leave town and have zero worries about our fur baby. Thanks Kris!”
“MeiLing responded to texts, sent pics of our dogs, and we returned home to 2 happy dogs and a clean house. Was friendly and the dogs seemed to really take to her. Would definitely use her again in the future!”
“Grace left our house clean and took good care of our pup. He was super happy for us to be back. She stayed in touch with us, which made it easier to leave him!”
“We just used Nadine for the first time and she was absolutely incredible with Puppy. She was so gentle, patient, and attentive. Easy to tell Puppy felt safe and comfortable with her right away. She even woke up early to match Puppy’s normal morning routine, which meant so much to us. Her communication was great, and it was clear she genuinely cared. Nadine is obviously a true pet lover, and it shows in how she interacts and connects. We would 100% book her again. Highly recommend her to anyone looking for a truly caring, reliable sitter. 💛🐾”
“Absolutely the best! She made my life so much easier for me and my animal family! She sent pictures and updates and was a huge relief when I needed someone last minute. Will definitely use her again!”
“Natalya was FANTASTIC! We are undergoing construction and everything was in disarray and dogs were unsettled. Should not have worried at all because Natalya had it handled. All communications were timely and we got fantastic pictures! So grateful for her and her handling of our 200 pounds of dogs.”
“Shando was amazing with our dogs. We have 2 very enthusiastic French bulldogs and he was able to calm them within moments of their initial meeting. He stayed in our home and took the dogs walking while we were away sending pictures and updates. When we returned home the dogs were so relaxed and happy. It was truly the best experience with a dog sitter we have had to date. We look forward to welcoming Shando back when we leave for another trip.”
“This was a Rebook with Jessica J. I prefer her as my sitter for Zion. She is the best sitter that I've ever had. Jessica follows instructions to the T. She is kind, caring, understanding and knows about dogs and their behaviors, etc. Zion took to her right away and loves playing with her with his toys. She walked him daily and sent us pictures and videos of him. While we were gone, we knew Zion was being well taken care of and thats a good feeling. With much appreciation, Mike & Rita”
“Olivia is so sweet and wonderful. I was able to leave on a work trip without any concerns about my home and pups. Received plenty of photos of happy, healthy guys who probably barely noticed I was gone as they were getting plenty of attention. Will definitely use her for the next trips to come as it's one less thing to worry about. Thanks so much!!”
“Jorie was an excellent and responsible sitter. My dog immediately warmed up to her and she kept me updated on my dog's status while I was away for the day. Will definitely be booking Jorie again!”
“Kelly was fantastic! She stayed at our house for 3 nights and watched our 17 year old siamese kitty Molly while we were out of town for the holidays. Kelly was quick to respond to every message and sent us lots of great photos and videos. Molly was very relaxed when we came home which is a clear sign of a good cat sitter. Highly recommend Kelly for your pets!”
Winchester pet parents share their Rover experiences
Natalya was great housesitting our 2.5 year old Frenchie for 5 days. He does not like new people and is very timid, but she got him to start warming up to her pretty quickly. She sent multiple updates throughout each day with pictures and was responsive. I left directions for her and she followed them. We came home to a happy dog. We will definitely be booking with Natalya again!
Jeter loves spending time with Jessica! She takes such great care and has amazing attention to detail. She ensured that he had a lot of enrichment, providing play, giving him his lick mat & puzzle toy, and taking him for a long walk. We look forward to booking her again!
Stephanie was absolutely incredible, and we couldn’t have asked for a better sitter. We have a multi-pet household with several cats, multiple who require daily medication, and a rabbit, so our daily needs are complicated! Stephanie handled everything flawlessly and went above and beyond in every way. She was extremely reliable, communicative, and thoughtful. She sent daily updates with messages and photos, which gave us so much peace of mind while we were away. It made such a difference being able to fully relax and enjoy our trip knowing our pets were in such capable and caring hands. When we got home, the house looked amazing—all the litter boxes were clean and everything was exactly how we left it. Most importantly, our pets were happy and comfortable, and it genuinely seemed like they bonded with her while we were gone. We felt complete trust and confidence in Stephanie from start to finish. She truly exceeded our expectations, and we would recommend her without hesitation to anyone looking for a dependable, attentive, and compassionate sitter.
We’re so glad we found Jorie! She was responsive and set up a meet and greet for us. Our pup Madden felt comfortable right away. Jorie kept us updated and was in communication our entire trip and sent photos of our pup a couple times each day which we loved!!! We felt at ease and our pup had a great time! We highly recommend! Thank you Jorie!
Yuliya was absolutely amazing! Our 3 pups took to her immediately and loved her. One of our dogs was coming off an eye infection and she was great with keeping up his eye drops regimen. She was by far the best sitter we've had when it comes to sending us regular pics and videos! She took some of the best pics/vids of the dogs that we have. They never pose like that for us...! It was very clear that they dogs were very happy with her and had an absolute blast. She is very communicative and one of the nicest people. My husband and I also became very friendly with her, as did our neighbors. She is very considerate and left our condo clean. The dogs clearly missed her after she left. We would absolutely rebook her for every trip of ours if she's available! Very highly recommended!
Kelly was fantastic! She stayed at our house for 3 nights and watched our 17 year old siamese kitty Molly while we were out of town for the holidays. Kelly was quick to respond to every message and sent us lots of great photos and videos. Molly was very relaxed when we came home which is a clear sign of a good cat sitter. Highly recommend Kelly for your pets!
We left our four dogs for the very first time, and we truly couldn’t have asked for a better sitter. She was absolutely amazing from start to finish- so kind, incredibly sweet, and clearly a true dog lover. She went above and beyond to make sure our pups were comfortable and happy. We got constant updates, photos, and check-ins, which made us feel completely reassured the whole time. It meant the world to know they were in such loving and capable hands. We can’t wait to use her again. Honestly, we couldn’t recommend her more!
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 Winchester is $50
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 Winchester average 4 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 Winchester on Rover as of Jun 2026 was about $50 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 1,621 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, 90% of Winchester house sitters respond in under an hour.
House sitters in Winchester have an average of 17 years of experience. House sitters with repeat customers have an average of 4 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.
Connect anywhere with the Rover app
