Dog Boarding in Winchester, CA
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
Prices are estimates per night for 1 dog. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Pet resort at Annie’s! Arlo’s favorite place to go. This time was no different only better as Arlo was super excited to get in when I dropped him off. It was a longer stay for Arlo this time, a month long but regular photo and video updates that showed how much fun Arlo was having kept me at ease. Thank you, Annie for taking such nice care of Arlo!”
“Trudy is an amazing sitter. She is very communicative and shows she cares deeply for the pups under her care. We will definitely continue to book with her in the future. Highly recommend!”
“Cannot emphasize enough how great Elsie is! She took such wonderful care of Bruno, and we truly appreciated the updates. The pictures she sent showed how comfortable and happy he was with her. Highly recommend!”
“Sandy and Jonas took great care of our dogs Bella and Raven. It was the first time we have left them with a sitter and we were a little nervous but we got lots of updates, videos and photos and it looked like they were having a great time and not missing us at all. Would 100% recommend.”
“Christina was fantastic! She sent me daily picture and video updates of Bandit. Her response time was excellent and most of all, Bandit was happy. I highly recommend Christina to care for your fur baby.”
“I am absolutely and completely impressed by the kind, genuine care and attention that Edgar and his wife shared with my lil guy Zion. The communication was very clear and consistent, that was so good. We are very grateful for them and recommend them 💯! We hope to be able to have them watch Zion again soon. Truly felt like he was with family. Thank you.”
“Paulena was amazing. Great communication. She understood my scarlets needs and welcomed her in made her feel right at home. Scarlet stay was 5 days She kept me updated with pictures and videos and my baby was just smiling thru the whole visit. I would recommend her 100xs over. We will definitely use her again in the future.”
“My pup had a wonderful stay with Jessica and her family. I will definitely use Jessica in the future when I need a safe, fun place for her to stay. Thank you, Jessica! Jane and Tosh”
“Vincent and Katie did an amazing job caring for my dobie babies . We felt at ease knowing they were in good hands . We really appreciated the updates and pics during there stay.”
“Absolutely one of the best experiences for our dogs. Needs 5 more stars. Michelle is very attentive and caring. She also provided occasional updates on our pups. Highly recommend.”
“Sandra was amazing to work with! She helped us with a very last minute change of plans and took fabulous care of our Patsy. She shared great photos and updates so we knew our baby was happy and safe. We will definitely be booking Sandra again!!”
“Alyx was amazing with Bosa! He had so much fun running around with her dog in her backyard. She even took him out to a doggy agility playground. Definitely would love to have him board over with her again!”
“Serena did a great job taking care of our dogs. She accommodated a meet & greet on short notice, and was flexible with the times to drop them off and pick them up. She updated us throughout the time we were gone with pictures, and she even took them on a hike! Our 8 month old puppy can be high maintenance at times, but Serena handled him without issue. I'd recommend her to anyone.”
“Tammi was so good with our Lucy. She sent updates daily and even brushed her out before she came home. Also, Tammi was very knowledgeable about our dog and provided us some very helpful feedback about caring for our Lucy, as she is a puppy still and we’ve only had her a couple of months. I highly recommend Tammi!”
Loving dog boarding sitters in your neighborhood
Search Results
Prices are estimates per night for 1 dog. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
Ramey K.
“Ramey has taken care of my little Sheepadoodle a couple of times now and she’s been absolutely amazing. We hope to have Ramey take care of her again in the future!! 🥰”
Annie S.
“Pet resort at Annie’s! Arlo’s favorite place to go. This time was no different only better as Arlo was super excited to get in when I dropped him off. It was a longer stay for Arlo this time, a month long but regular photo and video updates that showed how much fun Arlo was having kept me at ease. Thank you, Annie for taking such nice care of Arlo!”
Nora & David O.
“Nora went above and beyond for us! We felt so comfortable leaving our dog with Nora and her family. She was so accommodating and would recommend her to anyone”
Stephanie R.
“Stephanie was wonderful. Ford had the best time with her and the other pups. Made traveling a lot easier knowing how happy and well cared for he was. 10/10!”
Trudy G.
“Trudy is an amazing sitter. She is very communicative and shows she cares deeply for the pups under her care. We will definitely continue to book with her in the future. Highly recommend!”
Elsie R.
“Cannot emphasize enough how great Elsie is! She took such wonderful care of Bruno, and we truly appreciated the updates. The pictures she sent showed how comfortable and happy he was with her. Highly recommend!”
Sandy & Jonas W.
“Sandy and Jonas took great care of our dogs Bella and Raven. It was the first time we have left them with a sitter and we were a little nervous but we got lots of updates, videos and photos and it looked like they were having a great time and not missing us at all. Would 100% recommend.”
Christina E.
“Christina was fantastic! She sent me daily picture and video updates of Bandit. Her response time was excellent and most of all, Bandit was happy. I highly recommend Christina to care for your fur baby.”
Frank & Saleha B.
“Took great care of our Bella. Got regular updates and photos while we were away that were reassuring. Thank you for taking great care of our fur baby”
Edgar M.
“I am absolutely and completely impressed by the kind, genuine care and attention that Edgar and his wife shared with my lil guy Zion. The communication was very clear and consistent, that was so good. We are very grateful for them and recommend them 💯! We hope to be able to have them watch Zion again soon. Truly felt like he was with family. Thank you.”
Paulena G.
“Paulena was amazing. Great communication. She understood my scarlets needs and welcomed her in made her feel right at home. Scarlet stay was 5 days She kept me updated with pictures and videos and my baby was just smiling thru the whole visit. I would recommend her 100xs over. We will definitely use her again in the future.”
Jessica M.
“My pup had a wonderful stay with Jessica and her family. I will definitely use Jessica in the future when I need a safe, fun place for her to stay. Thank you, Jessica! Jane and Tosh”
Vincent N.
“Vincent and Katie did an amazing job caring for my dobie babies . We felt at ease knowing they were in good hands . We really appreciated the updates and pics during there stay.”
Michelle H.
“Absolutely one of the best experiences for our dogs. Needs 5 more stars. Michelle is very attentive and caring. She also provided occasional updates on our pups. Highly recommend.”
Sandra B.
“Sandra was amazing to work with! She helped us with a very last minute change of plans and took fabulous care of our Patsy. She shared great photos and updates so we knew our baby was happy and safe. We will definitely be booking Sandra again!!”
Alyx M.
“Alyx was amazing with Bosa! He had so much fun running around with her dog in her backyard. She even took him out to a doggy agility playground. Definitely would love to have him board over with her again!”
Jessica A.
“Jessica was amazing! She went above and beyond and even cane to pick our pup up and drop him off! Jessica stayed in contact and sent pics and videos. Highly recommend!”
Serena D.
“Serena did a great job taking care of our dogs. She accommodated a meet & greet on short notice, and was flexible with the times to drop them off and pick them up. She updated us throughout the time we were gone with pictures, and she even took them on a hike! Our 8 month old puppy can be high maintenance at times, but Serena handled him without issue. I'd recommend her to anyone.”
Breeanna A.
“Breeana was great and very happy with the care and communication!”
Tammi (Shigtastic) B.
“Tammi was so good with our Lucy. She sent updates daily and even brushed her out before she came home. Also, Tammi was very knowledgeable about our dog and provided us some very helpful feedback about caring for our Lucy, as she is a puppy still and we’ve only had her a couple of months. I highly recommend Tammi!”
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!
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, the median cost of dog boarding in Winchester is $50 per night, including service fees. Boarding your dog for one week typically costs $350. 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 $27 to as high as $55 per night.
As of Aug 2025, 779 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 17 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 779 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, 97% 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.
Connect anywhere with the Rover app
