Dog Boarding in Winchester
Find a loving dog sitter to watch your dog overnight at your sitter's home.
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Loving dog sitters in your neighborhood
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1. Oana & Oliver B.
“We had the best experience boarding our dog with Oana and Oliver. They were extremely caring, responsible, and kept us up to date with pictures every day (and the pictures they sent are extremely high quality!). After our meet and greet, we could immediately tell that Oana and Oliver were experts and thorough when it came to boarding. They asked detailed questions including dietary restrictions, how T-Rex prefers to eat/sleep/walk, and how T-Rex interacts with other dogs to make sure that T-Rex would have the best experience at their place. Oana and Oliver's place also has an amazing back yard that T-Rex enjoyed running around. They are also very communicative and we were able to travel with ease knowing that T-Rex was in good hands. We are definitely going to board T-Rex with them again in the future and we'd highly recommend Oana and Oliver to anyone who is looking for someone to trust their dog with.”
2. Yesika S.
“Yesika was an amazing sitter! She’s very communicative about the pet’s happiness and comfortability and she goes the extra mile to make sure they’re comfortable. She took excellent care of my dog Luke and I would love to book her again in the future.”
3. Surendra S.
“Our dog always has a great time here! Surendra is so good with communication and sends many photos and videos during the stay. We are SO grateful for her and her family providing a happy place for our pup!”
4. Betsy C.
“Betsy was a great sitter - very thorough and careful in getting to know my dog’s preferences and letting him see her very nice home and yard! Easy to communicate with and my pup seemed super happy :)”
5. Keunyung P.
“Keunyung and her husband did a fantastic job taking care of my dog Sugar over the holidays. Keunyung is very responsive and meticulous. She takes notes of every time she walks and feeds Sugar and sends me cute photos/videos. She even gave Sugar coconut water when noticing Sugar didn’t drink water. I can easily tell Sugar had a great time there. Would highly recommend Keunyung!”
6. Carol L.
“Wonderful! Carol has boarded my corgi several times now and she's been a pleasure to work with. She always take great care of my dog, she's communicative, flexible, and she's been available whenever I've needed her. Thanks Carol!”
7. Paul M.
“Paul was great, he was very easy to coordinate with (despite our running late to the drop-off). He was very responsive and sent cute photo updates. Thanks, Paul!”
8. Lissette A.
“Lissette was awesome! We've never boarded our dog Maggie before, but Lissette was great! We received pictures all week, and we loved that there were a couple other small dogs for Maggie to play with! I know she had a fun week, since she's been tired ever since we picked her up!”
9. Julia R.
“My cat did not want to come home! Cheddar was in such great hands with Julia - she was incredibly accommodating, administered medicine and sent many pictures. Plus her home is spacious and has many places for cats to hang out. Thank you again, Julia!”
10. Patrick G.
“Patrick was great and super responsive, sending me pictures of Albie throughout the day/ night he stayed with him. He also was thorough in making sure he understood Albie’s needs at the start of his visit, which made it even smoother. Would definitely ask him to watch Albie another time!”
11. Cassie S.
“Cassie and Alex were wonderful with our dog! She recently had radiation treatment so is on several medications. They had no problem giving her the medications twice a day. They also sent updates and pictures everyday!! We were so nervous to leave but felt instantly at ease with Cassie and Alex. This was the second week they took her. Will definitely be using them for all our future pet sitting needs. Highly recommend!!”
12. Hannah L.
“Hannah was amazing! She made a huge effort to keep our very active hound exercised and content. We also appreciated the regular communication while we were away. We absolutely recommend Hannah!”
13. Andy S.
“Andy was great and updated us frequently on how Freya was doing while we were away. I’m sure that Freya is looking forward to another stay in the future.”
14. Arnav J.
“Arnav is a very responsible and loving young man. He sent often photos of our puppy where we can tell that he was really taken care of and very loved. He and his family were always welcoming and stayed in communication with us. Our dog is part of our family and I would definitely rebook with Arnav, I highly recommend him. He will offer safety love and communication! Thanks Arnav ❤️”
15. Luciana R.
“We left our dog Sheila with Luciana and her mother for 1 night and it was a really good experience. We got regular updates and Sheila looked really happy through out her stay. The house is clean and they keep the dogs also clean throughout the stay.”
16. Cheuck L.
“Cheuck was great with Melo. Super friendly and great communication! It’s so nice to be able to travel and know that my pup was happy and well cared for.”
17. Rupendra & Lora S.
“Rupendra and Lora were AMAZING with our furry family member, Cooper! They sent me updates, including pictures and videos, on a regular basis and they were very flexible! I’m so happy that I no longer need to worry about Cooper while we are away!”
18. Adriana P.
“I felt so comfortable because Adriana is on time and took good care of my dog. She took my dog for walks often and provided everything he needed. I think she’s a really nice sitter.”
19. Kristin K.
“This was Romeo's first stay with Kristin, and I felt so lucky to have found her on Rover to watch him. Kristin gives 100% of herself from start to end of a stay for your dog. When meeting her for the first time she really got to know what Romeo's needs were, and assured me that he would be so loved and cared for through his whole stay. While I was away she asked me how I would like to kept in touch (do I like to get photos all the time to be assured he is having fun, or just from time to time so I could have fun on my vacation. This showed that she was not only thinking about Romeo, but also my needs as the owner). Romeo had a wonderful time with her adorable little babies (Waffles and Lucy). Her dogs are not only the cutest little pups, but so well mannered and calm. Romeo had so much fun whether it was walks around the neighborhood, playing with his new playmates, or snuggling in her bed. I recognize outstanding customer service when I see it, she definitely provided that and more. He was all ready when I said was going to pick him up. I even got a great progress report after. I could not have left my baby in better hands. This is assuring to me, as when I am away on a trip, I will know Romeo is having just as much fun. Thank you Kristin for absolutely everything!”
20. Ashley P.
“Ashley took wonderful care of our dog! She knew he needed exercise and took him on lots of long walks and played ball with him frequently. We would happily use her again.”
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1. Search
Read verified reviews by dog parents like you and choose a sitter who’s a great match for you and your dogs2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your dogs while you’re away3. Book & Pay
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Reservation protection
It doesn’t happen often, but if your dog sitter has to cancel, we’ll work with you to find a new sitter.
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Dog Boarding FAQs
Frequently asked questions about Rover
Sitters on Rover are free to set their rates. The median cost to hire a sitter for dog boarding in Winchester on Rover as of Jul 2024 was about $60 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 dog’s needs.
As of Jul 2024, 3,309 sitters provided dog 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, dog boarding sitters joining Rover must pass a background check for you and your dog’s safety.
Rover makes it easy to reach out to multiple sitters about your booking. Typically, 91% of Winchester dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Winchester have an average of 15 years of experience. Dog boarding sitters with repeat customers have an average of 9 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 dog boarding sitters to provide loving care from their own home. The background-checked, 5-star sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog boarding is great for:
- Dogs of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Dogs who’d love to socialize with their sitter’s pets
There are 3,309 dog boarding sitters in Winchester on Rover, so you’re sure to find the perfect match for your dog! In Winchester, 92% of sitters offer daily exercise, 94% offer medication administration, and 87% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog boarding sitter near you. As a reminder, sitters joining Rover must pass a background check for you and your dog’s safety.
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog 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 dog 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 dog boarding service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.