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

“We've used Rover sitters many times, and Yick-hong is one of the best! He clearly loves dogs and was great with our four-year old beagle Ruthie. He took her for a variety of walks, gave her doggie puzzles to solve, and snuggled with her on the couch. He sent us photos and videos two or three times a day. Will definitely call on him again to take care of our pooch.”


“Alix was amazing! She looked after Loki and took care of his special needs, she was friendly and caring. Will definitely seek her again when we need dog sitting support again.”

“John took great care of my high energy pup! His communication was excellent throughout the process and he too my dog on long walks. Looking forward to booking with John again soon!”


“Nathaniel was awesome and my dog was so happy with him. He took my dog hiking, swimming and outdoor events. Thanks for being so affordable yet a high quality dog sitter 🙏. He also sent us many pics and updates.”


“Chanel was responsive and responsible and seemed to really enjoy having our pup. She’s very sweet and sends updates and pictures everyday. Our pup seemed to really enjoy her stay and we’d book Chanel again!”


“Thank you so much for watching Harley! I could tell immediately that she felt comfortable/trusted you when I dropped her off and it made such a difference in allowing me to enjoy my trip. She’s already eaten the treat you sent her home with.”


“Jeongeun was amazing! Bruno was so well taken care of for the entire weekend he was with her. She is very caring and communicative. We couldn’t be happier and felt so reassured with Jeongeun! Thanks so much!”


“Michelle took great care of Stella and sent us lots of pictures and updates. It's easy to see how affectionate and caring she is with dogs. Also, when out return flight was delayed, she was flexible about adjusting our pick-up time.”


“Amy took a great care of my dog! He usually gets anxious at new places, but I can tell he was very comfortable and had a lot of fun at Amy's. I appreciate meet and greet before the boarding, and the updates throughout!”



“As always, Seamus and Bon went above and beyond to provide great care for Maybelle! We were away for several weeks and needed Seamus to drop off and pick up Maybelle from another sitter due to schedule conflicts. He handled the communication and transfer seamlessly, which set my mind at ease. Seamus sends great daily updates and I always know that Maybelle is extremely well cared for in his home.”


“Mia and Taowei were the BEST caretakers for our cocker spaniel, Dodger! I left him with them for 4 days. The minute Mia welcomed him into her living room, I could tell that Dodger felt at home. He walked around checking out the space and then immediately settled down. We brought his bed and a favorite animal so he had some familiar objects around him. Taowei played catch with Dodger, his favorite game, multiple times each day in the backyard. They took him for long walks around their neighborhood and let him explore to his heart's content. When he got wet in the rain, they even brushed and dried him off with a small hair dryer (which I am amazed he enjoyed). Dodger got so much love and attention from Mia and Taowei that we know from the pictures and videos they sent that Dodger had a fantastic time. We definitely will contact Mia and Taowei to take care of Dodger the next time we must go away. I can not think of a better and more caring household in which to leave our very special family pet.”


“I had a fantastic experience with Yi for Allie. She provided me regular updates and made sure she felt comfortable and happy while I was away. Allie was well taken care of, and I would definitely recommend them to anyone in need of a reliable sitter.”


“Jackie and her son Dylan were so good to Ruckus! They went for walks and had lots of playtime. I completely trust them and will be using her service from now on. Ruckus was so happy there that when I picked him up the next day he wasn’t even overly excited to see me! That proved to me he was very comfortable and felt loved.”


“JJ and Youfei did an amazing job taking care of my dog for 4 days and paid extra attention since my dog was not feeling well. JJ kept me updated with how my dog was doing and took extra walks and play time. They really treated my dog as their own. I would highly recommend them as sitters!”


“Knowing that Chaos was in such good hands and getting the pics of her on the trail hikes and just relaxing, was a great reassurance. Thanks for keeping me updated and I’m sure we’ll be in touch again!”



“Hannah was amazing. She let us visit twice before the stay so that Happy would be comfortable. Happy stayed over Thanksgiving, but Hannah sent me videos and pictures every day. I recommend her sitting service 100%.”



“Michael was very communicative and friendly. He made us feel comfortable leaving our dog with a sitter for the first time. He sent regular updates including pictures, which we greatly appreciated. Would definitely book with Michael again in the future! Thanks for taking great care of our pup!”

Loving pet boarding sitters in your neighborhood
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Yick-hong L.Star Sitter

“We've used Rover sitters many times, and Yick-hong is one of the best! He clearly loves dogs and was great with our four-year old beagle Ruthie. He took her for a variety of walks, gave her doggie puzzles to solve, and snuggled with her on the couch. He sent us photos and videos two or three times a day. Will definitely call on him again to take care of our pooch.”


Natasha K.


“We had an excellent experience with Natasha. She is attentive, detail-oriented, a great communicator, and clearly very caring. Highly recommend!”


Alix R.

“Alix was amazing! She looked after Loki and took care of his special needs, she was friendly and caring. Will definitely seek her again when we need dog sitting support again.”


John C.Star Sitter

“John took great care of my high energy pup! His communication was excellent throughout the process and he too my dog on long walks. Looking forward to booking with John again soon!”


Nathaniel F.Star Sitter

“Nathaniel was awesome and my dog was so happy with him. He took my dog hiking, swimming and outdoor events. Thanks for being so affordable yet a high quality dog sitter 🙏. He also sent us many pics and updates.”


Chanel K.
Star Sitter


“Chanel was responsive and responsible and seemed to really enjoy having our pup. She’s very sweet and sends updates and pictures everyday. Our pup seemed to really enjoy her stay and we’d book Chanel again!”


Todd V.Star Sitter

“Thank you so much for watching Harley! I could tell immediately that she felt comfortable/trusted you when I dropped her off and it made such a difference in allowing me to enjoy my trip. She’s already eaten the treat you sent her home with.”


Aurora C.Star Sitter

“Aurora was very responsive and excited to take care of Gnocchi! She sent pictures every day and brought the dogs out to the park almost every day as well!”


Jeongeun J.Star Sitter

“Jeongeun was amazing! Bruno was so well taken care of for the entire weekend he was with her. She is very caring and communicative. We couldn’t be happier and felt so reassured with Jeongeun! Thanks so much!”


Michelle C.Star Sitter

“Michelle took great care of Stella and sent us lots of pictures and updates. It's easy to see how affectionate and caring she is with dogs. Also, when out return flight was delayed, she was flexible about adjusting our pick-up time.”


Amy L.Star Sitter

“Amy took a great care of my dog! He usually gets anxious at new places, but I can tell he was very comfortable and had a lot of fun at Amy's. I appreciate meet and greet before the boarding, and the updates throughout!”




Séamus Ó.

“As always, Seamus and Bon went above and beyond to provide great care for Maybelle! We were away for several weeks and needed Seamus to drop off and pick up Maybelle from another sitter due to schedule conflicts. He handled the communication and transfer seamlessly, which set my mind at ease. Seamus sends great daily updates and I always know that Maybelle is extremely well cared for in his home.”


Mia & Taowei H.

“Mia and Taowei were the BEST caretakers for our cocker spaniel, Dodger! I left him with them for 4 days. The minute Mia welcomed him into her living room, I could tell that Dodger felt at home. He walked around checking out the space and then immediately settled down. We brought his bed and a favorite animal so he had some familiar objects around him. Taowei played catch with Dodger, his favorite game, multiple times each day in the backyard. They took him for long walks around their neighborhood and let him explore to his heart's content. When he got wet in the rain, they even brushed and dried him off with a small hair dryer (which I am amazed he enjoyed). Dodger got so much love and attention from Mia and Taowei that we know from the pictures and videos they sent that Dodger had a fantastic time. We definitely will contact Mia and Taowei to take care of Dodger the next time we must go away. I can not think of a better and more caring household in which to leave our very special family pet.”


Yi Z.Star Sitter

“I had a fantastic experience with Yi for Allie. She provided me regular updates and made sure she felt comfortable and happy while I was away. Allie was well taken care of, and I would definitely recommend them to anyone in need of a reliable sitter.”


Rob W.Star Sitter

“Rob was very accommodating for our high maintenance pup. She takes lots of meds and he handled it with aplomb. Hope he available again next time we're out of town!”


Jackie M.

“Jackie and her son Dylan were so good to Ruckus! They went for walks and had lots of playtime. I completely trust them and will be using her service from now on. Ruckus was so happy there that when I picked him up the next day he wasn’t even overly excited to see me! That proved to me he was very comfortable and felt loved.”


JJ & Youfei C.Star Sitter

“JJ and Youfei did an amazing job taking care of my dog for 4 days and paid extra attention since my dog was not feeling well. JJ kept me updated with how my dog was doing and took extra walks and play time. They really treated my dog as their own. I would highly recommend them as sitters!”


Yesika S.

“Knowing that Chaos was in such good hands and getting the pics of her on the trail hikes and just relaxing, was a great reassurance. Thanks for keeping me updated and I’m sure we’ll be in touch again!”




Hannah L.

“Hannah was amazing. She let us visit twice before the stay so that Happy would be comfortable. Happy stayed over Thanksgiving, but Hannah sent me videos and pictures every day. I recommend her sitting service 100%.”




Michael D.Star Sitter

“Michael was very communicative and friendly. He made us feel comfortable leaving our dog with a sitter for the first time. He sent regular updates including pictures, which we greatly appreciated. Would definitely book with Michael again in the future! Thanks for taking great care of our pup!”
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 pets2. Meet & Greet
Meet either virtually or in-person with a boarder to discuss the level of care needed for your 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 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.
Pet Boarding FAQs
Frequently asked questions about Rover
Typically, pet boarding sitters on Rover respond in under an hour, so you should be matched with the perfect sitter for you and your pet in no time!
Experience can vary widely from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when comparing sitters available 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
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.
