Dog Boarding in Winchester, WA
Find a loving dog sitter to watch your dog overnight at your sitter's home.
Every sitter passes an enhanced background check. Learn about RoverProtect
Top rated Winchester dog boarders
“Here's a review highlight that covers all the points you mentioned: "Our dog sitter was amazing! They provided regular picture updates, so we always knew our pup was happy and well cared for. Their professionalism shone through in every detail, from punctuality to the thoughtful communication. They treated our dog with such kindness, taking them on exciting hiking trips to local parks and ensuring they got plenty of exercise. They even brought along treats, which our dog absolutely loved! And of course, the cuddles—they made sure our furry friend felt loved and comforted while we were away. We couldn't have asked for a better sitter!"”
“Michaela far exceeded our expectations caring for our pup! Leaving our anxious little guy in anyone’s care is super unnerving for us and Michaela was so warm and welcoming to her. She sent us pictures and updates throughout the day and night and clearly created a safe, secure and truly loving environment for her. I wish all Rover boarders were as amazing as her. I give her my highest recommendation for anyone nervous about leaving their pup in a strangers care. She was the best!”
“I contacted Cassie about watching my pup Ginger while I was at the Gorge Amphitheater for a concert. This was my first time boarding Ginger & was a little worried but Cassie was so sweet & communicative throughout the entire visit I knew Ginger was in good hands! Would definitely recommend Cassie for any future boardings!”
“We couldnt be happier with the care Jordan and Cody provided for our dog!! From the start, communication was clear, friendly, and professional. They made sure to ask about our dogs routines, quirks, and preferences. While we were away, we received regular updates, including photos and little notes about how the day went. It was clear our dog was not only well cared for but genuinely loved. I would 100% recommend Jordan and Cody to anyone looking for a trustworthy, kind, and attentive sitter. We will absolutely be booking again!”
“Zander made sure we felt comfortable leaving our dogs with him and his family. This was a last minute reservation and I couldn't be happier with the care and consideration he took with our pups.”
“Kala took wonderful care of our dog on short notice. Communication was excellent. Her kennels are spacious, even for a 120lb dog. Her family took in our pup like one of their own. Thanks a ton, Kala!”
“Kaelyn was our lifesaver when she agreed to a last minute booking from us. Our dog Charlotte was so very well taken care of by her. We were sent updates and pictures daily and Charlotte looked so happy! Kaelyn kept Charlotte active with walks and plenty of outdoor play time. Thank you welcoming Charlotte into your home and caring for her.”
“Chelsea went over and beyond in caring for my older lab mix Riley. She and her family have her exercise and lots of attention. She came home very relaxed. Thank you Chelsea and Rover”
“A well deserved 5 stars! Lynn took such great care of my dog, providing me with occasional photos and updates. Her response time to texts was excellent. Will definitely be booking with her again!”
“I had such a great experience boarding with Teya and Trish! Honey Bun was clearly well cared for—she got to lounge in a luxurious cat tower, enjoy plenty of treats, and soak up all the love. I especially appreciated the regular photo and video updates. It gave me total peace of mind knowing she was in such good hands!”
“Jeff was excellent, I was able to vacation and relax with ease knowing the pups were safe with Jeff. We were away for two weeks and didn’t have any issues or concerns. I would recommend Jeff to any folks with dogs especially larger breeds. We left our two German Shepherds with Jeff and he provided them with exercise twice daily and paid special attention to our dogs specific needs. 5-stars for Jeff and the services he provided. We will be using him for all future dog stays.”
About: I have 3 dogs and 4 cats, that I trained myself. I love animals, am mature and responsible and have tons of free time to give attention to your pets. My kids are in high school now and no longer need my attention, so I have too much free time on my hands. I’m available all day everyday and can’t wait to play, walk, feed and cuddle your fur babies. I have a fenced in yard, but also take my dogs for walks or to the dog park for exercise, a change of scenery and to socialize them. My cats are indoor/outdoor so they require very little attention these days. I make sure they are fed and have water when needed, and I brush their coats and teeth weekly. I also give lots of cuddles and attention.
“Our regular sitter wasn't available so we decided to give Rover a try. We found Taylor M. and thought she'd be great for Clyde -- and we were right! He spent two nights in her home, we received regular updates with photos, and he was happy as a clam when we picked him up. Although we adore our regular sitter, we would definitely book Taylor again for Clyde to have the chance to play with Taylor and her dogs. You can tell right away she's a kind and patient animal lover.”
About: I have taken care of dogs, cats and birds! I am willing to take care of any other animal, as long as you provide a detailed care list!! Normally, I would take care of pets in the afternoons and on weekends I would be available all day. Currently, I am unable to have pets at my place. In other clients home I care for pets by making sure they’re close to me and or in proximity of the home. I find it it’s important to know where the pets are at all times because it only take 1 minute for them to find or do something terrible!
Loving dog boarding sitters in your neighborhood
Search Results
Jessica D.Star Sitter
“Here's a review highlight that covers all the points you mentioned: "Our dog sitter was amazing! They provided regular picture updates, so we always knew our pup was happy and well cared for. Their professionalism shone through in every detail, from punctuality to the thoughtful communication. They treated our dog with such kindness, taking them on exciting hiking trips to local parks and ensuring they got plenty of exercise. They even brought along treats, which our dog absolutely loved! And of course, the cuddles—they made sure our furry friend felt loved and comforted while we were away. We couldn't have asked for a better sitter!"”
Michaela & Ousta J.Star Sitter
“Michaela far exceeded our expectations caring for our pup! Leaving our anxious little guy in anyone’s care is super unnerving for us and Michaela was so warm and welcoming to her. She sent us pictures and updates throughout the day and night and clearly created a safe, secure and truly loving environment for her. I wish all Rover boarders were as amazing as her. I give her my highest recommendation for anyone nervous about leaving their pup in a strangers care. She was the best!”
Cassie U.
“I contacted Cassie about watching my pup Ginger while I was at the Gorge Amphitheater for a concert. This was my first time boarding Ginger & was a little worried but Cassie was so sweet & communicative throughout the entire visit I knew Ginger was in good hands! Would definitely recommend Cassie for any future boardings!”
Jordan & Cody H.
“We couldnt be happier with the care Jordan and Cody provided for our dog!! From the start, communication was clear, friendly, and professional. They made sure to ask about our dogs routines, quirks, and preferences. While we were away, we received regular updates, including photos and little notes about how the day went. It was clear our dog was not only well cared for but genuinely loved. I would 100% recommend Jordan and Cody to anyone looking for a trustworthy, kind, and attentive sitter. We will absolutely be booking again!”
Zander N.
“Zander made sure we felt comfortable leaving our dogs with him and his family. This was a last minute reservation and I couldn't be happier with the care and consideration he took with our pups.”
Tina C.
“This was the first time taking our 1 year old pup to a sitter. We got pictures to update how our pup was doing and Eos seemed to have a great time! Though a bit spoiled!”
Kala S.
“Kala took wonderful care of our dog on short notice. Communication was excellent. Her kennels are spacious, even for a 120lb dog. Her family took in our pup like one of their own. Thanks a ton, Kala!”
Niki F.
“Niki was great! Bernie had a blast with her dog and came home happy, healthy and went straight to bed haha. Thanks so much for taking care of him 😀”
Kaelyn B.
“Kaelyn was our lifesaver when she agreed to a last minute booking from us. Our dog Charlotte was so very well taken care of by her. We were sent updates and pictures daily and Charlotte looked so happy! Kaelyn kept Charlotte active with walks and plenty of outdoor play time. Thank you welcoming Charlotte into your home and caring for her.”
Chelsea E.
“Chelsea went over and beyond in caring for my older lab mix Riley. She and her family have her exercise and lots of attention. She came home very relaxed. Thank you Chelsea and Rover”
Lynn F.
“A well deserved 5 stars! Lynn took such great care of my dog, providing me with occasional photos and updates. Her response time to texts was excellent. Will definitely be booking with her again!”
TEYA & Trish P.
“I had such a great experience boarding with Teya and Trish! Honey Bun was clearly well cared for—she got to lounge in a luxurious cat tower, enjoy plenty of treats, and soak up all the love. I especially appreciated the regular photo and video updates. It gave me total peace of mind knowing she was in such good hands!”
Amanda W.
“Amanda is awesome!! We felt so comfortable leaving our dog with her and her kids, and she kept us in the loop with photos the whole time. Absolutely recommend!”
Jennifer T.
“Jennifer is awesome. Frequent pictures and videos to let us know our babies were safe and happy. House and yard were dog friendly and so is Jennifer.”
Alana P.
“Piper was well taken care of and really enjoyed staying with Alana and Legend. We will gladly recommend Alana for dog sitting and overnights!”
Jeff B.
“Jeff was excellent, I was able to vacation and relax with ease knowing the pups were safe with Jeff. We were away for two weeks and didn’t have any issues or concerns. I would recommend Jeff to any folks with dogs especially larger breeds. We left our two German Shepherds with Jeff and he provided them with exercise twice daily and paid special attention to our dogs specific needs. 5-stars for Jeff and the services he provided. We will be using him for all future dog stays.”
Margaux E.
“She is a very loving and caring person to both people and her pets, she makes sure they are fed, walked and never alone for too long. They have a big yard so both cats and dogs have room to roam safely.”
Taylor M.
“Our regular sitter wasn't available so we decided to give Rover a try. We found Taylor M. and thought she'd be great for Clyde -- and we were right! He spent two nights in her home, we received regular updates with photos, and he was happy as a clam when we picked him up. Although we adore our regular sitter, we would definitely book Taylor again for Clyde to have the chance to play with Taylor and her dogs. You can tell right away she's a kind and patient animal lover.”
Yoselin H.
About: I have taken care of dogs, cats and birds! I am willing to take care of any other animal, as long as you provide a detailed care list!! Normally, I would take care of pets in the afternoons and on weekends I would be available all day. Currently, I am unable to have pets at my place. In other clients home I care for pets by making sure they’re close to me and or in proximity of the home. I find it it’s important to know where the pets are at all times because it only take 1 minute for them to find or do something terrible!
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 $50
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.
Dog Boarding FAQs
Frequently asked questions about Rover
As of Aug 2025, 9 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.
Typically, dog boarding sitters on Rover respond in under an hour, so you should be matched with the perfect sitter for you and your dog in no time!
Experience can vary widely from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when comparing sitters available 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 9 dog boarding sitters in Winchester on Rover, so you’re sure to find the perfect match for your dog! We understand that each dog is unique and may require specific 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.
Connect anywhere with the Rover app
