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
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

“Alexsys was amazing!!!! She was always so quick to respond and always sent an update each day on how my pup was doing. Sent videos and pictures of all the fun he was having and made it so easy for us to enjoy our trip without worrying about how he was doing. When my kids expressed how much they missed him she even sent extra pictures so they could see how much fun he was having. I would definitely recommend Alexsys and will definitely be using her again :)”



“Tamara was so sweet, thoughtful, and helpful with our anxious pup. She picked him up, took fantastic care of him, sent plenty of updates during our time away, and brought him home happy and relaxed. She was super accommodating, too, when we needed to change our timing for pickup. We can’t wait to have Tamara watch our little guy again! It’s so nice to find a reliable, kind, easygoing person to watch our dog when needed. Tamara is absolutely awesome!!!”


“Henry had such a wonderful time with Linda and really enjoyed his time there. Linda was so nice to send us updates throughout the day and pictures. We are so happy to have Linda so close to where we moved and I know Henry is too!”


“Joshua and Kristen are always awesome. They take such good care of my dog as if she were one of theirs. I love the continual photos and updates they provide. I always feel so good/comfortable when they watch Lulu!!”


“We cannot recommend Jaclyn enough! She has always been an amazing caregiver for our pup, treating him like part of her family with love, attention, and plenty of playtime. But what truly sets her apart is her incredible kindness and flexibility. When our flight was unexpectedly canceled at the last minute, Jaclyn didn’t hesitate to extend our pup’s stay for a few extra days, giving us one less thing to stress about. It's rare to find someone so reliable, caring, and genuinely dedicated to both pets and their owners. Our pup always comes back happy, well-cared-for, and loved. If you’re looking for the best, Jaclyn is it! Thank you, Jaclyn! You’re a lifesaver! 🐶❤️”


“Anahita was great. She met with me ahead of time (conveniently over video) and went over details to make sure my Bruno would be a good fit for her and her smaller dogs. She is experienced and understanding. We needed a bit of flexibility on the drop-off and pickup because of our road trip and she was very accommodating. Thanks Anahita!”


“Walter and his family continue to take amazing care of our puppy. When leaving today, she whimpered - that’s a sign of a happy girl! We are so happy to have found this loving family. Thank you again for all that you do to make Harper feel right at home. We look forward to working with you again soon!”


“Janelle & Joel are absolutely fantastic! This was my first time using Rover, and I am so glad I chose them. They sent pics of my pup having the time of his life! Nothing better than having the peace of mind when leaving your fur baby for a weekend! Thanks you two! Will gladly be a returning client!”


“We always feel reassured that our pup is taken care of and they’re happy to have her. Daisy is treated like the princess she is. I highly recommend their family to watch your beloved pets.”


“Gabby is awesome! She took such loving care of our dog, offering updates and adorable photos throughout the stay. Came back to a happy and well-cared-for pet. Highly recommend Gabby!”


“She was great with my 2 huskies. My husband and I received pictures daily. She asked questions with any concerns she had while they stayed with her. We will definitely use her again and refer her to anyone we know who needs a furry baby sitter. Absolutely loved the updates and pictures. Thank you for taking such good care of them”


“Kalley is an amazing sitter. She took awesome pictures and updated me daily on how my baby was doing. Thank you so much Kalley. We’ll be booking with again soon!”



“It was made apparent how experienced she is. She watched our 4 month old puppy for the weekend, and by the photos and videos she sent he was VERY happy!! Responds quickly and great communication! We definitely plan to use her again the future :)”


“Bella did a phenomenal job watching Luna. We were in need of new overnight boarding arrangements and we hit the jackpot finding her. We organized a meet and greet before our pup stayed with her so Luna was very comfortable coming back to stay for the weekend. We received many videos and pictures updates during her stay.. putting our hearts and minds at ease while we enjoyed our trip our of town. I highly recommend her and we will be rebooking in the near future! Thank you for caring for Luna like your own family!”


“We left our dog with Jessica for the weekend. She took great care of her & updated us with pics & videos . We will be booking with her again & highly recommend her !”


“Haejin and Herscel were amazing with my elderly dog and made me feel so much more comfortable while being away from him. The provided detailed updates and you can tell they really care. Highly recommend!”


“I had to leave on a business and Lisette was able to look after my cat Ogden. Communication was quick and simple, and Lisette was very accommodating . I have no problem recommending this sitter.”

Loving dog boarding sitters in your neighborhood
Search Results
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.


Alexsys T.Star Sitter

“Alexsys was amazing!!!! She was always so quick to respond and always sent an update each day on how my pup was doing. Sent videos and pictures of all the fun he was having and made it so easy for us to enjoy our trip without worrying about how he was doing. When my kids expressed how much they missed him she even sent extra pictures so they could see how much fun he was having. I would definitely recommend Alexsys and will definitely be using her again :)”




Tamara G.

“Tamara was so sweet, thoughtful, and helpful with our anxious pup. She picked him up, took fantastic care of him, sent plenty of updates during our time away, and brought him home happy and relaxed. She was super accommodating, too, when we needed to change our timing for pickup. We can’t wait to have Tamara watch our little guy again! It’s so nice to find a reliable, kind, easygoing person to watch our dog when needed. Tamara is absolutely awesome!!!”


Linda E.
Star Sitter


“Henry had such a wonderful time with Linda and really enjoyed his time there. Linda was so nice to send us updates throughout the day and pictures. We are so happy to have Linda so close to where we moved and I know Henry is too!”


Joshua & Kristen B.Star Sitter

“Joshua and Kristen are always awesome. They take such good care of my dog as if she were one of theirs. I love the continual photos and updates they provide. I always feel so good/comfortable when they watch Lulu!!”


Jaclyn S.
Star Sitter


“We cannot recommend Jaclyn enough! She has always been an amazing caregiver for our pup, treating him like part of her family with love, attention, and plenty of playtime. But what truly sets her apart is her incredible kindness and flexibility. When our flight was unexpectedly canceled at the last minute, Jaclyn didn’t hesitate to extend our pup’s stay for a few extra days, giving us one less thing to stress about. It's rare to find someone so reliable, caring, and genuinely dedicated to both pets and their owners. Our pup always comes back happy, well-cared-for, and loved. If you’re looking for the best, Jaclyn is it! Thank you, Jaclyn! You’re a lifesaver! 🐶❤️”


Anahita T.Star Sitter

“Anahita was great. She met with me ahead of time (conveniently over video) and went over details to make sure my Bruno would be a good fit for her and her smaller dogs. She is experienced and understanding. We needed a bit of flexibility on the drop-off and pickup because of our road trip and she was very accommodating. Thanks Anahita!”


Walter G.
Star Sitter


“Walter and his family continue to take amazing care of our puppy. When leaving today, she whimpered - that’s a sign of a happy girl! We are so happy to have found this loving family. Thank you again for all that you do to make Harper feel right at home. We look forward to working with you again soon!”


Joel & Janelle E.Star Sitter

“Janelle & Joel are absolutely fantastic! This was my first time using Rover, and I am so glad I chose them. They sent pics of my pup having the time of his life! Nothing better than having the peace of mind when leaving your fur baby for a weekend! Thanks you two! Will gladly be a returning client!”


Barbara D.


“I absolutely made the right choice when booking her. She was great with nug and sent a picture about every day. She and her family loved and spoiled nug”


Michelle M.Star Sitter

“We always feel reassured that our pup is taken care of and they’re happy to have her. Daisy is treated like the princess she is. I highly recommend their family to watch your beloved pets.”


Gabby T.Star Sitter

“Gabby is awesome! She took such loving care of our dog, offering updates and adorable photos throughout the stay. Came back to a happy and well-cared-for pet. Highly recommend Gabby!”


Shaghayegh H.
Star Sitter


“She was great with my 2 huskies. My husband and I received pictures daily. She asked questions with any concerns she had while they stayed with her. We will definitely use her again and refer her to anyone we know who needs a furry baby sitter. Absolutely loved the updates and pictures. Thank you for taking such good care of them”


Kalley B.Star Sitter

“Kalley is an amazing sitter. She took awesome pictures and updated me daily on how my baby was doing. Thank you so much Kalley. We’ll be booking with again soon!”




Katherine B.Star Sitter

“It was made apparent how experienced she is. She watched our 4 month old puppy for the weekend, and by the photos and videos she sent he was VERY happy!! Responds quickly and great communication! We definitely plan to use her again the future :)”


Yzabella V.

“Bella did a phenomenal job watching Luna. We were in need of new overnight boarding arrangements and we hit the jackpot finding her. We organized a meet and greet before our pup stayed with her so Luna was very comfortable coming back to stay for the weekend. We received many videos and pictures updates during her stay.. putting our hearts and minds at ease while we enjoyed our trip our of town. I highly recommend her and we will be rebooking in the near future! Thank you for caring for Luna like your own family!”


Jessica I.Star Sitter

“We left our dog with Jessica for the weekend. She took great care of her & updated us with pics & videos . We will be booking with her again & highly recommend her !”


Haejin & Herscel L.

“Haejin and Herscel were amazing with my elderly dog and made me feel so much more comfortable while being away from him. The provided detailed updates and you can tell they really care. Highly recommend!”


Zachary T.Star Sitter

“Zachary did an amazing job watching my two dogs. He checked in with me everyday and sent photos as well. I really appreciate him taking great care of them!!”


Lisette R.

“I had to leave on a business and Lisette was able to look after my cat Ogden. Communication was quick and simple, and Lisette was very accommodating . I have no problem recommending this sitter.”


Katie R.

“Katie was an absolute angel for our pups during their stay with her. She stayed on top of their health and wellbeing and kept us well informed. Would 100% use again!”
Over 940 pet parents in Winchester have booked dog boarding
Winchester dog parents share their Rover experiences
I was so nervous to leave our little fur baby with someone other than family but Nyla immediately bonded with Allison and her beautiful family! I could tell she would feel comfortable being there and that was most important. During our time away, Allison sent pictures and she was very communicative in person and afterward. This was Nyla’s first time being around kids and Allison said she was great around them. We would definitely book her again or even drop Nyla off for doggy daycare so she can become more comfortable with Allison and her family for future drop offs. When we picked her up she seemed just as happy than when she did her meet and greet!

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 dogs2. Meet & Greet
Meet either virtually or in-person with a boarder 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!
The median cost per night for dog boarding in Winchester is $45
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 14 repeat dog boarding clients
Dog Boarding FAQs
Frequently asked questions about Rover
As of Aug 2025, the median cost of dog boarding in Winchester is $45 per night, including service fees. Boarding your dog for one week typically costs $315. 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 $26 to as high as $53 per night.
As of Aug 2025, 206 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, 90% of Winchester dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Winchester have an average of 21 years of experience. Dog boarding sitters with repeat customers have an average of 14 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 206 dog boarding sitters in Winchester on Rover, so you’re sure to find the perfect match for your dog! In Winchester, 96% of sitters offer daily exercise, 96% offer medication administration, and 93% 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.
