Dog Boarding in Winchester, CA
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 for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“I was very satisfied with the care my dog, Bandit, received with Frank, Saleha, and their 2 sons. They kept me updated with pictures and videos while I was on vacation. I couldn't have asked for a better boarding for my dog. I would use them again and highly recommend them if you need someone to watch you furry friend.”
“So incredibly grateful for Delaney and her family for taking such good care of our Coco, I know she had the best time and was so happy to be around her new doggy friends. I appreciate all the little updates throughout the week and also appreciate the little paw print and picture they sent home! 😊 I know Coco is going to miss everyone, until the next time 🧡”
“Stephanie is THE BEST. Ford is excited to staycation with her and always comes home happy and exhausted from the attention and love he gets from her. The hardest part about leaving home is Ford but knowing he is well taken care of makes having to travel at times leave. Thank you so very much for another sleep over (this was a week) and taking such great care of my boy.”
“Melissa is great! 11+/10 and I highly recommend her. She is bubbly and super friendly and we can tell that our pup will be in great hands. She communicated with us well and send daily video and photo updates. She treated and cared for Stella like her own. She was able to pick her up and dropped her off for us which made it even more amazing coz she helped us with that aspect of transportation. I will definitely contact you again Malissa. You just gained us and we thank you very much. U are beyond when u actually came back to make sure Stella gets her bed back that same night. So thoughtlful…”
“Jessica was absolutely amazing! She communicated with us every step of the way and made us feel so at ease by sending pictures and videos of our fur baby. She was incredibly accommodating to our needs and very attentive. Stella clearly felt right at home and definitely made a new friend—we can’t wait to visit Jessica again soon! Highly recommend! 🐾💛”
“We left our dog for six days and it seemed like we were still there with all of the pictures Rachelle sent everyday ! She has a nice big yard and lots of room elsewhere for the dogs to play. You can tell she is a very caring person and thank goodness we found her for our future trips!”
“I can’t thank Jessica enough for always accepting my request to watch my baby at such a short noticed. She’s such a great sitter. I can trust that she’ll keep me posted with pictures and videos of how much fun my baby is having. I know that my baby is in good hands with Jessica.”
“Chanelle did a great job with our two doggie’ long term stay. She shared photo updates regularly. She has a safe home with a lot of covered outdoor space for the dogs to run around and play. Will book her again for sure!”
“Paulena was an amazing sitter for our dog. We received regular communication and felt comfortable that our dog was being taken care of. I highly recommend and would use her services again in the future”
“Abigial is the best sitter i could have imagined! She was super responsive and caring with my dog and i could tell my dog had a great time with her. I will definitely be rebooking with her and i definitely recommend her!”
“Trudy is awesome!! So thankful for her and for opening her wonderful home to our pup! He was treated like their own! Nothing better than knowing your pup is comfortable in someone else’s home while you’re away! I highly recommend her and appreciate her hospitality! We will definitely be using her again and again!! :)”
“Maverique is young and very large. She loves people and other dogs, but is also excitable when entering a new situation. Breanna handled her very well and I am very pleased with her services.”
“Serena is great! She was quick to respond to the request and was great with communication all throughout. I’m a helicopter a mom and get anxious leaving Cappuccino with a sitter, but I felt very at ease with Serena and was able to enjoy my vacation knowing that Cappuccino was being well taken care of. Serena was attentive to his needs, making sure he ate because he likes to go on a hunger strike when I’m away, and kept me well updated. Kevin, her dog, is super sweet and well behaved, I think Cappuccino enjoyed meeting him and spending time with him. Definitely would trust her with my baby again.”
“Our Monty had a wonderful time with Heather, Jesse and their kids. He had so much love from them and was so happy to be with them. They always sent me updates and pictures daily and we truly appreciate it. Monty missed them so much after we picked him up. Will definitely use Heather and Jesse again.”
“Thee best dog care givers ever! Our Oso loves his stays with Melissa and Richard. Detailed updates and photos keep me from missing him while knowing he’s in great hands. Thank you guys again!”
“I could not be happier or say enough good things about Savannah. She is just awesome and if you are able to get your dog booked with her. You are in good hands! Not only did my standard poodle play like a fun, crazy dog the whole time, but he is still asking to go out, to see if his friends are still there! LOL. She did a wonderful job and I cannot think of a better sitter! She has exceeded all of my expectations and more. She has a great vibe and my Luke Skywalker loved her!”
“Audrey, was exactly the person I wanted to take care of my pooch while I was out of town. She is responsive, responsible, easy going, and a solid communicator. Her dog played great with ours and he seemed happy when I got there to pick him up. In short, she’s somebody that I will look forward to leaving my dog with again the future.”
“Megan was amazing with my baby Branch! This was the first time leaving my fur baby with someone else while I went on vacation so I was very nervous. However, I was able to be relaxed and comfortable during my vacation with having Megan. Megan was so good to Branch and he warmed up to her in no time which put me at peace. Megan was very communicative and sent constant updates and pictures of Branch. Branch absolutely loved Megan! I will most definitely be booking with Megan again!”
“Sandra is truly the perfect pet sitter. Chloe and Spencer received so much love, attention, and care while I was away. I appreciated the frequent updates and photos, which gave me complete peace of mind. Both of my fur babies ate well every single day—something any pet owner knows isn’t always the case when boarding—so I knew immediately they were comfortable and happy. I wouldn’t hesitate to book with Sandra again and again. She’s amazing, and I’m so grateful for the care she provided. I will definitely book with Sandra again—highly recommend her to anyone looking for a caring and reliable sitter.”
“Kim was amazing. The kids had a great time. She was very delightful and an overall amazing person. I look forward to requesting her for boarding in the future. Thank you, Kim,.”
Over 1,592 pet parents in Winchester have booked dog boarding
Winchester dog parents share their Rover experiences
Diane was the best pet sitter I've ever hired. She listens, asks great questions, and communicates daily when requested. She treats the pets as if they are her own. The home was amazing and her dog Duke was a great playmate for my two dogs. I highly recommend booking with her!
Tammi’s the best! We have a Malinois that we needed help with. Our girl, Nymeria, can be a handful as a high energy, high drive pup. It’s pretty tough to find someone who understands her and we feel we got lucky finding Tammi. She did some training with her and helped us address behavioral issues. She communicates very well with us and is happy to answer any questions. We’ve definitely noticed the progress in Nymeria when it comes to jumping on people, waiting for direction, and how to behave/play with other dogs. She also loves playing with Tammis pup Ollie and usually comes home very tired. We’re definitely going to continue to book with Tammi.
We had a wonderful experience with Alexsis as our dog sitter! Molly and Lucy stayed with her and were treated like part of the family. Alexsis was extremely communicative and sent us daily updates with adorable pictures, which gave us such peace of mind while we were away. It’s clear she and her family truly care for the dogs they watch. We will absolutely be rebooking with her in the future!
Popular requests near you
Select a filter and find qualifying Winchester sitters!How Rover works
1. Search
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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
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The median cost per night for dog boarding in Winchester is $50
Why Choose Rover?
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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 Mar 2026, 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 Mar 2026, 840 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 840 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, 97% offer medication administration, and 96% 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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