Dog Boarding in Winchester
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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 and her family took great care of my Joey when I got a last minute invitation to take a trip. I appreciate that she was available at the last minute when my usual boarding facility was completely booked. She sent me texts everyday and also sent pictures. If I had any questions, she got right back to me. I really appreciated all of that. Thank you, Alexsys!”
“Walter and his family are amazing! We are new pet owners and they let us come over for a meet and greet prior to booking to help calm our nerves. Our puppy was excited to be there with his caring children. He would give us updates with pictures and videos throughout her stay. When our flight was delayed and diverted to another airport, Walter was gracious enough to have her stay one more day. Thank you for taking such great care of our girl! We look forward to working with you and your beautiful family again soon!”
“Josh and Kristen are absolutely awesome. They truly cared about Lulu and took great care of her. They sent me so many pictures, with updates....even videos. They treated Lulu just like she was part of their beautiful family. I am actually utilizing them again later this month. Wonderful, caring people.💪💪❤️❤️”
“Shaghayegh has always been a great sitter for our sweet fur buddy. Always kind, prompt, responsive, and clearly compassionate; we wouldn’t hesitate to recommend her. Many thanks! Beau looks forward to his next visit :)”
“Gabby is amazing! She accommodated our baby super last minute and saved a very important trip for our family. She’s extremely responsive, keeps you updated with plenty of photos and messages, and it’s very obvious that her entire family is full of animal lovers. They spoiled our big rambunctious Cane Corso puppy more than we could have wished for in a sitter. Highly recommend and will definitely use again! Thank you, Gabby and family!”
“Renee and Chris wonderful people and are amazing at what they do. They care for our Chloe like their own. Renee sends us pictures and videos to keep us posted. We have been taking Chloe to them for almost 5 years now.”
“We are so pleased with the care Penny received during her 5 day stay with Linda. It is evident that Linda loves animals and cares for them well.”
“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!”
“Even thought this was his first visit to Michelle, Rusty was very comfortable wth Michelle and her family. He seemed relaxed and happy when we picked him up. I am sure he enjoyed the large fenced back yard.”
“Lori was amazing with our fearful German Shepherd Fiona. this was our first time booking with Lori and she took pictures every day we were gone and gave us updates. It made us feel so much better. When we brought Fiona home she was so much happier than she has been leaving her with other people or a kennel. So grateful for Lori and her husband and we will definitely be using her again.”
“Katherine has the trifecta of dog boarding/watching: her property is amazing, her pack of dogs are charming, and her heart and love of dogs is quite evident. Our beagle, Gates, has stayed twice with Katherine, and he comes home happy and exhausted from playing with her dogs. We don’t worry while we are doing our thing because we know Gates is being cared for and enjoying his time. Thank you, Katherine for being so wonderful for dogs!”
“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!!”
“Jaclyn was great! She had Midnight for 3 nights while we were out of town and from the pictures, it looks like he had a great time getting cuddles from her and her other pups!”
“Haejin was amazing!! I loved how she always sent me pictures and videos and kept me updated! I felt such relief knowing that they were in very good hands.”
“Tamara was great! She was so accommodating at the last minute and my pup really seemed to have had fun while in her care! Would absolutely recommend her!”
“Jessica was wonderful, I’m not sure my poodle missed me at all. She sent me regular updates, pictures and videos. Sometimes he was happily lap sitting. Sometimes she videoed him playing with toys her dog or interacting with her family. I was gone 10 days. I was happy to see him doing so well. He is a picky eater so I had sent cubed up chicken breast to mix with his food. When she ran out she cooked him another, which was going way above what I expected. I would definitely take my dog to Jessica again.”
“Such wonderful animal lovers! I received nightly photos of our dog having the best time on their property. Would recommend them to everyone and will use them again.”
“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!”
“Bella is an amazing Pet Sitter and dog groomer! This is the first time anyone has ever kept my Pom so I was a little nervous. All those nerves were put to reset the moment we met and you assured me my puppy was in good hands. I appreciate all the messages and photos you sent. These are some of the best photos I have of my puppy! I will definitely book you again and recommend you to outer pet owners.”
“Barbara was fantastic! We received daily updates with pictures. Would recommend her wholeheartedly to anyone looking for a sitter. Will definitely use her again.”
Loving dog boarding sitters in your neighborhood
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Alexsys T.Star Sitter
“Alexsys and her family took great care of my Joey when I got a last minute invitation to take a trip. I appreciate that she was available at the last minute when my usual boarding facility was completely booked. She sent me texts everyday and also sent pictures. If I had any questions, she got right back to me. I really appreciated all of that. Thank you, Alexsys!”
Walter G.
Star Sitter
“Walter and his family are amazing! We are new pet owners and they let us come over for a meet and greet prior to booking to help calm our nerves. Our puppy was excited to be there with his caring children. He would give us updates with pictures and videos throughout her stay. When our flight was delayed and diverted to another airport, Walter was gracious enough to have her stay one more day. Thank you for taking such great care of our girl! We look forward to working with you and your beautiful family again soon!”
Joshua & Kristen B.Star Sitter
“Josh and Kristen are absolutely awesome. They truly cared about Lulu and took great care of her. They sent me so many pictures, with updates....even videos. They treated Lulu just like she was part of their beautiful family. I am actually utilizing them again later this month. Wonderful, caring people.💪💪❤️❤️”
Shaghayegh H.Star Sitter
“Shaghayegh has always been a great sitter for our sweet fur buddy. Always kind, prompt, responsive, and clearly compassionate; we wouldn’t hesitate to recommend her. Many thanks! Beau looks forward to his next visit :)”
Gabby T.Star Sitter
“Gabby is amazing! She accommodated our baby super last minute and saved a very important trip for our family. She’s extremely responsive, keeps you updated with plenty of photos and messages, and it’s very obvious that her entire family is full of animal lovers. They spoiled our big rambunctious Cane Corso puppy more than we could have wished for in a sitter. Highly recommend and will definitely use again! Thank you, Gabby and family!”
Renee K.Star Sitter
“Renee and Chris wonderful people and are amazing at what they do. They care for our Chloe like their own. Renee sends us pictures and videos to keep us posted. We have been taking Chloe to them for almost 5 years now.”
Linda E.Star Sitter
“We are so pleased with the care Penny received during her 5 day stay with Linda. It is evident that Linda loves animals and cares for them well.”
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!”
Michelle M.
“Even thought this was his first visit to Michelle, Rusty was very comfortable wth Michelle and her family. He seemed relaxed and happy when we picked him up. I am sure he enjoyed the large fenced back yard.”
Lori V.Star Sitter
“Lori was amazing with our fearful German Shepherd Fiona. this was our first time booking with Lori and she took pictures every day we were gone and gave us updates. It made us feel so much better. When we brought Fiona home she was so much happier than she has been leaving her with other people or a kennel. So grateful for Lori and her husband and we will definitely be using her again.”
Katherine B.Star Sitter
“Katherine has the trifecta of dog boarding/watching: her property is amazing, her pack of dogs are charming, and her heart and love of dogs is quite evident. Our beagle, Gates, has stayed twice with Katherine, and he comes home happy and exhausted from playing with her dogs. We don’t worry while we are doing our thing because we know Gates is being cared for and enjoying his time. Thank you, Katherine for being so wonderful for dogs!”
Zachary T.
“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!!”
Jaclyn S.Star Sitter
“Jaclyn was great! She had Midnight for 3 nights while we were out of town and from the pictures, it looks like he had a great time getting cuddles from her and her other pups!”
Haejin & Herscel L.
“Haejin was amazing!! I loved how she always sent me pictures and videos and kept me updated! I felt such relief knowing that they were in very good hands.”
Tamara G.
“Tamara was great! She was so accommodating at the last minute and my pup really seemed to have had fun while in her care! Would absolutely recommend her!”
Jessica I.Star Sitter
“Jessica was wonderful, I’m not sure my poodle missed me at all. She sent me regular updates, pictures and videos. Sometimes he was happily lap sitting. Sometimes she videoed him playing with toys her dog or interacting with her family. I was gone 10 days. I was happy to see him doing so well. He is a picky eater so I had sent cubed up chicken breast to mix with his food. When she ran out she cooked him another, which was going way above what I expected. I would definitely take my dog to Jessica again.”
Joel & Janelle E.
“Such wonderful animal lovers! I received nightly photos of our dog having the best time on their property. Would recommend them to everyone and will use them again.”
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!”
Yzabella V.
“Bella is an amazing Pet Sitter and dog groomer! This is the first time anyone has ever kept my Pom so I was a little nervous. All those nerves were put to reset the moment we met and you assured me my puppy was in good hands. I appreciate all the messages and photos you sent. These are some of the best photos I have of my puppy! I will definitely book you again and recommend you to outer pet owners.”
Barbara D.Star Sitter
“Barbara was fantastic! We received daily updates with pictures. Would recommend her wholeheartedly to anyone looking for a sitter. Will definitely use her again.”
Over 931 pet parents in Winchester have booked dog boarding
Winchester dog parents share their Rover experiences
Shay always treats my dogs like a part of her family! We appreciate having a dog sitter that we trust!🐶
Alexsys was terrific! She was very attentive, flexible, and sent us pictures and videos of our pup daily. Highly recommend. We will be using her services again!
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!
Kyla was, is, and always will be the BEST. Our dogs and cats have enjoyed the benefits of her conscientious, caring, and cheerful care for three years. As we must now relocate out of the area, we are doubtful that we will be able to find anyone who matches Kyla's level of service to our critters, and to us.
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 $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 13 repeat dog boarding clients
Dog Boarding FAQs
Frequently asked questions about Rover
As of Jul 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 $52 per night.
As of Jul 2025, 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, 92% of Winchester dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Winchester have an average of 19 years of experience. Dog boarding sitters with repeat customers have an average of 13 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, 96% of sitters offer daily exercise, 96% 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.
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