Dog Boarding in Winchester
Find a loving dog sitter to watch your dog overnight at your sitter's home.
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Top rated Winchester dog boarders
“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.”
“I definitely wanna give a HUGE SHOUT OUT to Dina, she has been super amazing. The moment I think about my Dog, I am already getting a text that she is doing exceptionally well. I was so nervous to drop off my puppy to a stranger. But Dina has made me and my wife worry free. I definitely recommend her, and I will 100 percent use her again for future pet sitting. Also the pictures she has sent me of my puppy every single day, has been nothing but amazing to see that my dog is doing so well. Thank you so so so much. I will recommend her to anyone.”
“Gloria was amazing with my Riley! I contacted her super last minute due to an emergency and she was very willing to accommodate our needs- she even gave him a bath! I cannot recommend her enough. We’ll be booking again with Gloria!”
“When we needed a sitter last minute on vacation Emily came to the rescue and was one of the best dog sitters we have ever had. Emily sent pictures through the day, followed all our care instructions and loved our baby like we do.”
“Natasha was a good communicator and sent pictures of our girl while we were away! She took our golden on walks and played with her. She also was a huge help to us by picking up and dropping off our golden when we had early/late flight times. She was a huge help and we felt great about leaving our Honey girl with Natasha!”
“Andrew is the best sitter for senior pups. I travel a lot for work and i know Marlo is well taken care of when Andrew watches him. Cosmo is an amazing pup friend to Marlo.”
“Megan takes such good care of Sophie! Sophie is on more meds now that she’s older and Megan is so good about asking any questions and keeping up with the medication chart. We were unable to fly home after the Caribbean air space was shut down and Megan kept Sophie even longer until we returned. We appreciated it so much. We will definitely book with Megan again!”
“Erin was fantastic! She sent pictures and updated me and it was obvious Dudley was having a great time. My flight was delayed and she was completely understanding and happy to keep Dudley a few extra hours. I definitely plan to re-book with Erin! Highly recommended.”
“I am so thankful to have found Melody. My dog, Opal, took to her right away, and she LOVES being over there for daycare and overnight stays. The times are super flexible, and I’m thankful to have someone that loves my dog as much as I do! I get pictures and videos on how Opal is doing throughout the day. Definitely the best dog sitter in Lex!”
“Addie is fantastic!! We met her twice before we left town just to be sure things were all set— and our dog loves her. We were flexible about where she stayed with our dog- her house or ours- because we were gone for 16 days. She did everything she could to make sure we were comfortable with her. She sent pictures, responded quickly to texts, and Levi’s know how everything was going. Additionally, Addie is a genuinely nice person who is driven in her work as a dancer. We were very impressed with her. We are looking forward to many more trips, knowing our dog is safe and well loved in our absence.”
“We went out of town for a week leaving our one year old Bulldog with Nef. He came to meet our dog and even accommodated transportation. My dog is very picky on who she likes however it was love from first sight. This was the first time we had to board our dog and now we have our go to person for life. Thanks Nef for the outstanding service!”
“Eggbert had a great time! I could tell by his behavior and poop he was well cared for. I did get pictures and updates which was much appreciated. Will book again ❤️🎶”
“This was my fourth time taking Duncan to Kath & Jordan and as always, they took great care of him! He always looks so happy in the pictures they send me :)”
“Jennifer has taken care of our Labradoodle since moving here to Lexington 2 years ago. We have been very happy because our dog is happy when he stays with her and happy when he comes home. This trip we ran into travel delays because of the storms last night here in Kentucky. Jennifer was so accommodating with our travel delays. Thank you Jennifer for taken good care of our dog.”
“Kelsey was awesome with my Great Dane zeke. He usually has a rough time at boarders when he’s in a crate and won’t eat,drink etc. Kelsey went above and beyond to make sure my big guy was taken care of and comfortable. He went on walks,car rides and even had a heated mattress cover on him.he is worn out.i would use her again and advise anyone to use her. She will go above and beyond to make sure your pets are comfortable.”
“Amazing experience! I was very nervous about leaving him but Cheyenne, her family, and her dogs were amazing and Koda had so so much fun! We will definitely be sending him again!”
“Our puppy had a wonderful time staying with Ana and her dog, Mia. Ana was an excellent sitter very accommodating, communicative, and easy to work with. We felt completely at ease and would happily book with her again.”
Over 107 pet parents in Winchester have booked dog boarding
Winchester dog parents share their Rover experiences
Amazing, adaptive, accommodating, and so thoughtful! Vanessa asked great questions, really cared about our Duke’s preferences and routines, and gave us many helpful tips and insights. She has more experience than us with dogs, so I learned a lot in our short time together. I’ll definitely use her again as long as I can make the trip to her. Love!
Popular requests near you
Select a filter and find qualifying Winchester sitters!How Rover works
1. Search
Read verified reviews by dog parents like you and choose a boarder who’s a great match for you and your dogs
2. Meet & Greet
Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs 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 dog boarding in Winchester is $37
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 boarding sitter has to cancel, we’ll work with you to find a new dog boarding sitter.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Sitters in Winchester average 9 repeat dog boarding clients
Dog Boarding FAQs
Frequently asked questions about Rover
As of Jun 2026, the median cost of dog boarding in Winchester is $37 per night, including service fees. Boarding your dog for one week typically costs $259. Sitters on Rover set their own rates based on their qualifications, your dog's needs, and their space's amenities. As a result, most Winchester dog boarding rates can be found as low as $20 to as high as $38 per night.
As of Jun 2026, 199 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, 95% of Winchester dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Winchester have an average of 14 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 199 dog boarding sitters in Winchester on Rover, so you’re sure to find the perfect match for your dog! In Winchester, 95% of sitters offer daily exercise, 95% offer medication administration, and 95% 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.
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