Pet Boarding in Winchester
Find a loving Winchester pet sitter to watch your cat or dog overnight at your sitter’s home.

Every sitter passes an enhanced background check. Learn about RoverProtect
Top rated Winchester pet boarders
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“I was in a pinch and needed someone reliable to keep Wiilow. I didn't want to leave her at a kennel or dog boarding facility because she would spend most of the time in a crate. Linda was the answer. She had a great place with huge backyard. Her home was equipped just right. Linda updated me with pictures via dogvacay throughout the day to assure me Willow was ok. Willow loved it! I would highly recommend her services.”

“Carrie was a life saver. Our original sitter cancelled on us at the last minute and Carrie took Ranger with no problem. He had the BEST time playing with all the other dogs and I know he was loved on. Ranger became ill while in her care (NO fault of anything at her house—just a fluke) and Carrie communicated with us and took great care of Ranger, maybe even spoiled him ;-). We would send Ranger to her again in a heartbeat. Very much recommend!!”

“Heather was great! Kept me informed on how my dog Cody was doing and sent pics of him with her dogs. Cody seemed to love her Lab. Lots of room to run in her fenced in back yard. Will definitely use her again!”

“We have been using Audrey a couple of times, and my dog feels at home when he is with her. She sent me photos and an update on how he is doing. I recommend her 100 percent.”

“Lauren was absolutely amazing with our pup!! I couldn't recommend her more!! She is SO kind and caring. I could tell from the moment we had a meet and greet with her and her pups. She provided us daily updates on our pup and treats your pets just as she does her own. I was so relieved to find someone that I can trust our beloved furbaby with from now on. I was kind of upset that my pup wasn't more excited to come home, but that's just a reflection of the good time she had on her little vacay!! 🤣 Highly recommend Lauren for all your fur baby care!!”

“We’re so grateful for the love and care our pups received. It meant everything knowing they were not just safe, but truly happy while we were away. The sweetest part was how much our doggies adored her kids you could tell they were having the best time together. We came home to a couple of relaxed, happy dogs, and that says it all. They will be going back forever now!”

About: I care for every pet as if they were my own, making sure they always feel safe, comfortable and loved. I spend quality time playing with them, giving plenty of attention, affection, and reassurance. Daily walks are a favorite part of my routine, allowing pets to stay active, happy, and relaxed. I also gently reinforce basic training and good manners to provide consistency and positive structure. My goal is to create a calm, loving environment where pets feel at home and owners feel complete peace of mind. Also a very great pet chef if needed. Available for house sitting or dog walking on weekends from Friday afternoon through Monday afternoon. Perfect for worry free weekend getaways! So plan your weekend trip and leave you fur babies with me! I have a fenced in backyard and two dogs of my own that would loved to keep your dogs company! My dogs love playing with balls and taking naps (dog crates if needed).

“Leaving our dog with Kristen was the best boarding experience she'd ever had! We don't often take a vacation without our dog, but the handful of times we had in the past, she was traumatized when I picked her up. She isn't crate trained and hates the little kennels at the vet and other commercial boarding facilities. Kristen's farm was like a vacation for her while we were on vacation! She loved the big open yards, having the run of the house, and being around the other dogs. Kristen is a warm, caring, responsible animal lover. It was like our old girl went to stay with a favorite aunt for a week! When I picked her up, she was dirty and tired and happy. ? Such a wonderful experience! We will always board with Kristen, as long as she can take us”

“Tetiana did a lovely job looking after our dog, Charlie. Thank you for the photos and updates while we were gone! We'll definitely have Charlie stay with Tetiana again! Thank you!”

“We had such a great experience with this dog boarding home! We felt completely at ease the entire time he was there. We loved getting regular updates with pictures, videos, and texts throughout the week — it made such a difference seeing how happy and well cared for he was. By the end, I was almost worried he wouldn’t want to come home because he was having so much fun! Highly recommend if you’re looking for a loving, attentive place for your pup. 🐾”

About: Animals have been a part of my life since birth, and caring for them comes naturally to me. While I currently have three cats, I’ve spent a lifetime around dogs and understand their needs, behaviors, and personalities. I have a deep compassion for animals and have rescued several over the years. In addition, I’ve been hosting an Airbnb for the past five years, where I’ve regularly cared for and pet sat for my guests’ animals, building trust and hands-on experience with pets of all kinds. Their safety, happiness, and well-being always come first. I treat every pet as if they were my own—providing a safe, loving, and stress-free environment. Your pet will never be just a job to me—they will be treated like family every single time. I work for myself, I have a very flexible schedule and can adjust my time to meet your pet’s needs. This allows me to be available, reliable, and fully present for your pet. Whether it’s daily visits or extra attention while you’re away, I’ll make sure they are cared for, comfortable, and never feel alone. I treat every pet like my own, with safety and comfort always coming first. I live on a private five-acre property with a large, securely fenced-in yard where dogs can safely play and enjoy plenty of space. Inside, pets have a calm, clean environment with cozy spots to relax, along with toys and attention. I always supervise outdoor time and make sure every pet feels safe, comfortable, and truly cared for.
“Abby has watched our dog Rocky several times and has always done a wonderful job! Rocky is a rescue, and a terrier, and she let him take his own time getting to know her and her 2 dobie's (both great). This last time presented some unusual challenges, and Abby went above and beyond to make sure Rocky felt safe with her and that we could continue our vacation. She has always communicated well, and has been fantastic with all of her care. I would highly recommend her for your pet!! I can't say it enough. She's great.”


“Charity is so easy to work with. We travel a lot for sports and never really know when we are going to be back but Charity works with us to figure out what works best for us and her family. And we love the pictures she sends!”

“Jennifer was great and I would definitely recommend her to anyone who wants their dog well taken care of. She provided constant updates, gave him lots of play time, and sent plenty of pictures of him having a blast while I was away. Will definitely be using her again in the future.”

“i’m a repeat client with Anahita. she is very caring and took such a great care for my dog , Leo. we feel confident leaving our pet in her care . highly recommended. thank you Anahita”

Winchester pet parents share their Rover experiences
Karen was absolutely amazing with our dog, Stella. From the moment we dropped her off, we could tell she and her husband truly care about animals. They treated Stella like she was their own and spoiled her with love (and plenty of treats). We really appreciated the daily updates and pictures, it made being away so much easier knowing she was happy and in great hands. Karen also kept us in the loop on how Stella was doing around the other dogs, which we loved. You can genuinely tell just by talking to them how passionate they are about caring for animals. Their experience with rescue groups really shows in the way they handle and love the dogs they watch. We wouldn’t hesitate to trust Karen again and highly recommend her to anyone looking for someone who will treat their pet like family.

Popular requests near you
Select a filter and find qualifying Winchester sitters!How Rover works

1. Search
Read verified reviews by pet parents like you and choose a boarder who’s a great match for you and your pets
2. Meet & Greet
Meet either virtually or in-person with a boarder to discuss the level of care needed for your pets 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 pet boarding sitter has to cancel, we’ll work with you to find a new pet boarding sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
Pet Boarding FAQs
Frequently asked questions about Rover
Typically, pet boarding sitters on Rover respond in under an hour, so you should be matched with the perfect sitter for you and your pet 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 pet boarding sitters to provide loving care from their own home. The background-checked, 5-star sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet boarding is great for:
- Dogs and cats of all ages and abilities, including puppies and kittens
- Pet parents looking for a safe, loving alternative to a kennel or hotel
- Pets who’d love to socialize with their sitter’s pets
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet 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 pet 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 pet boarding service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.









