Pet Boarding in Winchester
Find a loving Winchester pet sitter to watch your cat or dog overnight at your sitter’s home.
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Top rated Winchester pet boarders
Prices are estimates per night for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“March took great care of my dog, Hatley!! He took him for walks on wooded trails and sent picture updates. Hatley looked very comfortable and happy at his house. Thanks, March!”
“I can’t say enough amazing things about Likun—she is truly the BEST dog sitter we’ve ever had! From the moment Chewy arrived, he was showered with so much love, attention, and care. 🐾💛 She spent tons of time playing with him and made sure he was always happy and engaged. Her large backyard was an absolute dream—plenty of space for Chewy to run around, explore, and have the time of his life! It honestly felt like a mini vacation for him. What really stood out was the 1-on-1 attention she gave him. You can tell she genuinely cares about the dogs she looks after, and Chewy absolutely adored her. I picked him up relaxed, happy, and clearly very well cared for. If you’re looking for someone trustworthy, attentive, and full of love for your pup, Likun is it. We will definitely be booking with her again—Chewy can’t wait to go back!”
“Michelle was fantastic! We were lucky she was available to take care of our dog for an extended weekend. Tito came back home a happy pup! We would happily book again.”
“Carol is fantastic! Our pup stayed with her for February vacation week and had a blast. She was very quick and kind with her communications — and sent pictures and videos throughout our vacation. Our flight was delayed, and she was very accommodating about adding an extra night for us. Will definitely book again if she’ll have us!”
“I am very happy for the service provided by Yulia. My malti-poo dog has been given very good care by Yulia and her very nice/friendly family. I will request Julia for dog care service in next time again. Thanks Yulia!”
“Jonathan is an exceptional dog-sitter, our pet was very well cared for, exercised, and received lots of affection and attention. Jonathan was also very accommodating when we needed to extend our stay by a day at the last minute. Would recommend and will certainly book with again!”
“Elizabeth and Neil, along with their dogs Beam and Percy, gave our dog such a fun weekend! They sent frequent pictures and videos so I could see what he was up to. Highly recommend!”
“Chanel was wonderful! She not only took our little guy on short notice but she was also very flexible with drop-off and pick-up times. She sent updates and pictures of him. He seemed very happy and content. Highly recommend her!”
“Hunter had a great overnight stay with John. John took him on several walks and made sure he was fed and comfortable. Our dog sometimes gets anxious and John knew how to calm him. John gave us regular updates and photos. We appreciated the reporting for Hunter's very first overnight with him. TY John!”
“This was my first time using Rover.com and Marilyn could not have been a better choice for my little rescue dog. Right from the first introduction my dog took to her right away. Marilyn is very knowledgeable about pet care, and she is very welcoming and easy to talk to. She clearly loves animals and has a great setup in her home. I would not hesitate to leave my dog with Marilyn again. Thank you for the great service!”
“My dog had an excellent time with Kaisi. Kaisi sent lots of pictures of her dog and mine at the dog park, walking in fresh pond, looking so relaxed and happy. Thanks Kaisi!”
“Rebeca and her husband were great! They sent lots of pictures and updates throughout Walter's stay. He looked very happy and tired from all the walks and play time. We will absolutely use them again. Thanks!”
“We can't thank Lori G. enough for taking care of our precious pups while we were on vacation! Lori provided frequent updates including multiple pictures and videos which made us feel connected to our pups while away! She kept our pups active by bringing them on walks and played with them inside and outside her home in her fenced in back yard! Lori G. is a wonderful person with a special love for dogs, and quite evident that our pups were more than well cared for!!! We most certainly will have Lori G. take care of our pups again!!! Thank you so much Lori G. (:-)”
About: My husband and I have been around dogs our whole lives and truly enjoy caring for them together. We have our own adult Labrador, whom we adopted when she was about one year old, so we understand how important it is to create a calm, attentive environment for a dog when their owners are away. Over the years, we’ve also cared for dogs for friends and family, and we always focus on making them feel safe, comfortable, and settled in a home setting. We provide a low-stress, relaxed environment and pay close attention to each dog’s personality and energy level — some enjoy playing, while others prefer to rest and stay close to people, and we’re happy to adjust accordingly. One of us is home most of the time, so dogs are rarely left alone and always have company and attention throughout the day. Our goal is to make them feel as comfortable and secure as possible while you’re away. I work from home, so dogs are rarely left alone and always have company throughout the day. Most of the time, both my husband and I are home, which allows us to give dogs plenty of attention and care. We’re flexible and adjust the day depending on each dog’s needs and energy level. Dogs in our home are always supervised, and we pay close attention to their behavior, comfort, and interactions. We introduce new environments calmly and give dogs time to settle in at their own pace. We follow each dog’s routine closely, including feeding, walks, and any specific instructions, and we avoid sudden changes that could cause stress.
“Arnav did a great job. Buck had a hot spot arise right before my travel. He came home after my trip with significant healing accomplished. He went to his stay a bit anxious, not quite himself, and when I picked him up from Arnav, he was at ease. Arnav communicated regularly and well. He sent pictures. He asked questions. We discussed how to treat Bucks hot spot, and made some decisions together from a distance that worked well. Highly recommend Arnav for your dog.”
“"It's as if she never left!" - Our dog Bella has stayed with Rob several times, and was delighted to be back. Rob and his family take great care of her (walks, feeding, treats, loving) and make her feel a part of both the people and dog families!”
Winchester pet parents share their Rover experiences
Ari and Sara are fantastic sitters, and I highly recommend them! They have watched Pipa several times and she is always so excited to go back to their house and see them. She gets along great with their dog, Bond, and always comes home happy and relaxed. Ari and Sara are incredibly responsive, flexible, and genuinely caring. It gives me great peace of mind knowing Pipa is in such good hands with them when I have to go away.
JJ and Youfei are the best! They take such good care of our corgi Chewy, sending so many pictures and videos and taking her on walks everyday. We can rest assured knowing that Chewy is well taken care of, and is having a great time with them and Nano. They are our favorite sitters and we always look forward to Chewy’s stays with them!
I had a great experience. Bok was excellent at communicating and sending photos and updates, and took excellent care of my dog Gatsby. Bok was very punctual and at the same time accommodating when my flight was delayed. My dog was clearly happy to to stay with Bok and his loving family, I could tell it from all the photos, and I felt that Gatsby liked it so much that he was even a bit reluctant to leave😅 I will be happy to use Bok’s services again. Totally recommend it!
Left Reggie while we were overseas and was 100% confident that he was in good hands and having a good time. He's can be kind of hesitant, but Belinda was in tune with him and very aware of how he and the other dogs interacted with one another, and she genuinely seems to really like having the pups around. Her house is a great setup, with a fenced in yard and lots of space indoors for multiple dogs to be there at the same time. Will absolutely leave Reg with her again!
Heather took great care of my goldendoodle (Riva) for a weekend. Heather was very communicative and shared pictures and updates throughout the stay, and it was comforting to see Riva looking so relaxed and at home. She seemed to fit right into Heather's family! I would definitely recommend Heather to others.
Booking with Noila was a great experience. She took amazing care of our two cats, kept us updated with cute photos every day, and was highly communicative. It’s such a relief to know your pets are in good, capable hands. We will definitely be reaching out to her again for future needs!
Aysegul and her husband took amazing care of our cat, Momo. She had a wonderful time and actually relaxed, played, and ate - all things that are very unusual for her when we travel. Aysegul shared several updates and adorable photos of Momo throughout the day, which really put us at ease and made it so much easier knowing she was doing well. We highly recommend them!
This was my second time leaving Brody with Cheuck and Michael. They were fantstic as always, took incredibly good care of Brody, sent me photo and video updates, and even gave us a goodie bag of pet treats to take home with us when I went to pick Brody up. I always feel very reassured leaving Brody with them - I know he'll be well looked after and happy. Definitely recommend these guys!
Ann was a wonderful sitter for Maisy. We had a complex situation because our dog had some health concerns arise right before her stay but Ann was very reassuring and gave Maisy lots of loving care and support. She is clearly very experienced and had some good insight and resources to offer more generally about our aging dog's situation. Thanks Ann!
Popular requests near you
Select a filter and find qualifying Winchester sitters!How Rover works
1. Search
Read verified reviews by pet parents like you and choose a boarder who’s a great match for you and your pets
2. Meet & Greet
Meet either virtually or in-person with a boarder to discuss the level of care needed for your 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 pet boarding in Winchester is $63
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 pet boarding sitter has to cancel, we’ll work with you to find a new pet boarding sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
Sitters in Winchester average 10 repeat pet boarding clients
Pet Boarding FAQs
Frequently asked questions about Rover
Sitters on Rover are free to set their rates. The median cost to hire a sitter for pet boarding in Winchester on Rover as of Jun 2026 was about $63 per night, after factoring in Rover’s service fees. A sitter’s rate may also change as you customize your booking to fit your and your pet’s needs.
As of Jun 2026, 4,174 sitters provided pet boarding in Winchester. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, pet boarding sitters joining Rover must pass a background check for you and your pet’s safety.
Rover makes it easy to reach out to multiple sitters about your booking. Typically, 91% of Winchester pet boarding sitters respond in under an hour.
Sitters who provide pet boarding in Winchester have an average of 16 years of experience. Pet boarding sitters with repeat customers have an average of 10 repeat clients. Experience can vary from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when you compare sitters in Winchester.
Rover makes it easy to find Winchester pet boarding sitters to provide loving care from their own home. The background-checked, 5-star sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet boarding is great for:
- Dogs and cats of all ages and abilities, including puppies and kittens
- Pet parents looking for a safe, loving alternative to a kennel or hotel
- Pets who’d love to socialize with their sitter’s pets
There are 4,174 pet boarding sitters in Winchester on Rover, so you’re sure to find the perfect match for your pet! In Winchester, 91% of sitters offer daily exercise, 95% offer medication administration, and 88% have experience with senior pets and pets with special needs. We know each pet is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet boarding sitter near you. As a reminder, sitters joining Rover must pass a background check for you and your pet’s safety.
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet boarding sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your 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 pet boarding 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 pet boarding service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.
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