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. Sarah W.

“Took very good care of my dogs, one of which has separation anxiety and had only ever been left with family prior. If you need a caring and professional sitter, she will not disappoint. Very highly recommend.”


2. Shelby B.

“Shelby was awesome! She was available on a short notice and sent pictures and updates all throughout my dogs stay. Will definitely be using her again!”


3. Andrew C.

“Andy did a great job helping Nate feel at home. Nate got snacks he likes and outside breaks that were on his schedule. Andy sent a lot of updates with pictures. Besides the cute pictures, Andy sent me a picture that showed Nate feeling relaxed. Frankly, I was glad Nate still wanted to come home! Andy understands dogs, has an appreciation for the variety of normal dog behavior, and really does love dogs. His daughter also really loves dogs. Although I found Andy through Rover, a mutual friend confirmed that he’s a dog lover and would trust him with her dogs. Knowing that we had mutual friends was literally an answer to prayer. I would definitely trust this family with Nate again.”




4. Erin S.

“Erin and her husband were amazing!! They took excellent care of our dog, Nash, while we were traveling. He got numerous walks while staying with them and came home ready to nap (which is always nice when we are also coming back from traveling)! Would highly recommend and Nash absolutely cannot wait to stay with his new friends again!”


5. Voss L.

“Voss did a great job with my dog!! She was happy when I picked her up and not stressed at all! You can tell Voss loves animals and takes pride in taking good care of them. Will definitely use Voss again!”


6. Kath & Jordan R.

“Kath and Jordan were excellent! Max felt right at home with them. They sent pictures daily and the communication was stellar. Highly recommend!”


7. Amy H.

“Our Bibi had the best time with Amy and Murray. We received lots of updates and photos. Amy treated Bibi like one of her own and we will definitely re-book with her, the next time we travel. If I could leave SIX STARS, I would.”


8. Sarah R.

“sarah was just fabulous with 🐶🥰. she was loving, attentive, followed our guidelines, reported often with photos and personable in addition. we highly recommend her and will certainly request her in the future. thks sarah.”


9. Jordan L.

“Jordan is Fiona’s best sitter so far. She is very communicative and sends lots of cute photos and updates, I didn't even have to ask. I enjoyed my trip to Istanbul knowing Fiona was in safe hands. Also loved seeing Fiona around her family and other dogs. ❤️”


10. Kristin F.

“Thank you Kristin and family. I didn’t worry about Asher and Luna while in your care, and that is a blessing! They must have had fun because they are zonked out!”


11. Elena S.

“Elena is amazing. This isn’t the first time she has cared for our babies and they love her. She is great with them and sends pictures all the time to keep us updated while we are away. We will definitely use her again when we travel.”


12. Madison A.

“Madison was amazing!!! Ranger is a very energetic pup and he had the best time with her and her dogs. She worked with all my requests and sent tons of pictures. I would give 10 stars if I could!!! I will definitely recommend her.”


13. Jennifer B.


“Jennifer is so thorough, and she and her dog have provided a delightful environment for Lulu to play, rest and enjoy herself! Lulu highly recommends her! (Told me so herself!)”


14. Micki O.

“I was a little worried about how Buckeye would do because he does not socialize a lot. He was a little nervous at 1st but quickly got to know the other dogs and had so much fun!! Micki was great and sent me pictures of how he was settling in on the 1st day when I was really worrying about him. She is extremely comfortable around animals and I am so glad to know there's a great place to take Buckeye whenever I need to leave town!”


15. Sarah G.
“What a great sitter! They took my dog while we were in Brazil for two weeks. She sent photos and our dog seemed so happy. She even schedule and took her to a groomer since she need it so bad and I didn’t have the time to take her. Lovely experience. Book with her!”


16. Brian C.
“Communication and understanding and ability to accommodate on the fly was outstanding. Nova came back to me happy and relaxed. Would definitely recommend Brian to anyone and will definitely rebook.”


17. Cheyenne C.

“Can't rave enough about this Rover. Pups are always so well taken care of! Truly their home away from home with the added benefit of furry buddies to play with. Cheyenne is super flexible willing to work with your needs, communicates promptly, and handles all aspects of the pups. Highly recommend.”


18. Amber W.
“Amber was a great sitter for our dog Lola, and we would definitely choose her again! Throughout our week-long vacation, we enjoyed getting pictures and updates of Lola having fun with Amber's other dogs. Loved that they have a fenced yard and are home a lot. Also, when our plane was canceled and we had to extend our booking by a whole day, Amber was super sweet and accommodating. Definitely recommend her to watch your pup!”


19. Jennifer G.

“Jennifer was very nice and kept me updated on Tito the whole time I was away. Very nice home and Tito was wore out the day I picked him up! Can’t wait for Tito to visit her again!”


20. Ebony H.

“Our girl Amelia had a great time with Ebony are her furbaby! We got pics and updates on how was doing as it was her first time staying with anyone!”
How Rover works
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
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 dog sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
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 $35 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, 187 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, 96% of Winchester dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Winchester have an average of 16 years of experience. Dog 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 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 187 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, 100% offer medication administration, and 92% 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.
