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

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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.


“Major had another great time, seems he even met some new doggie pack friends 😀 love how much space he has to run around, always comes back tired, which is a great thing.”


“Jaclyn had all of her ducks in a row. My first time sitting with her and she answered all of my questions and asked really good questions of her own. I was comfortable that she has planned how to safely and comfortably keep new dogs at her house. Even if they’re of the nervous type like mine. She also kept me updated daily with messages and photos which we really appreciated. Thank you, Jaclyn, for taking such great care of Bini.”



“Chris, what an exceptional job. When I first met Chris, it was very obvious he was just excited to hangout with my pup. Dropping her off was simple and gave me a lot of confidence for Indys Stay. Chris sent me pictures during the entire 6 days he cared for Indy. Picking her up, they had already been out on a nice walk and it was obvious because she was very tired. I plan on using Chris again and would recommend anyone to entrust Chris with their Animal.”



“We couldn't be any happier with the care Juicy received from Charity. She was incredibly sweet, kind, and responsive, making us feel at ease leaving our furchild in her hands as we traveled. Juicy was treated like one of her own, and we appreciated how accommodating she was throughout the entire process. The pictures and videos were also a nice touch. Five stars without a doubt!”


“I was looking for a place to board Sake that was a mid-point between my home to Bryce Mountain to go skiing. I found Maki who was on the way to the slopes. She was very accommodating when I forgot the dry food (Mom Brain), but luckily I brought enough wet food for Sake's meals. I appreciate they were very patient with Sake trying to sleep in her crate at night while I am attempting to crate train her. I was worried she might be howling most of the night, but surprisingly, Sake ended up napping inside her crate after we got home today. This is a new behavior for Sake which I am so happy to see!!!! This is a good sign that she is dreaming of all the fun walks and attention she got from Maki and her family. She shared photos and informed me on all of her walks, her desire to chase a squirrel, and when she peed, pooped, finished her meals, got several belly rubs and chilled at the house. I highly recommend you go to Maki whenever you need boarding. She is conveniently located on the way to the slopes. Upon pick up, her son was kind to carry the crate out to my car and place it in my trunk. I noticed that Sake's belongings were neatly folded, cleaned and organized inside the overnight bag. Sake will definitely return when I need to go back to the mountains for the weekend or day when I am not able to bring her with me. Thank you for taking good care of her. When I see Sake sleeping well after her visit from boarding, that is a positive sign that she had an awesome time with the family.”


“We left our two dogs with Mallary for over a week. She took good care of them and sent pictures everyday. Thanks to her, we were able to enjoy our vacation knowing that the dogs were in good hands. The dogs were happy and healthy when we picked them up. They weren't in any hurry to leave and kept looking for Mallary's dogs, their new friends. It was so sweet. Thank you, Mallary! We will be back!”


“Abby did a wonderful job watching our dog! We had a meet and greet the week prior that went great, her two dogs are sweet and playful and got along with ours well! I’m not sure our dog wanted to come home she was so happy there!!”


“Audrey is amazing!!! She took great care of my two dogs while me and my family were out of the country for 9days. She is very knowledgeable and passionate about them. I recommend her and will contact her again in the next time we need her. Thanks Audrey! ?”


“Lots of TLC and a safe environment are top priorities when we select a dog sitter for our golden doodle. Sarah and her family all gave so much care and kindness to our pup. Frequent walks on her quiet street and a daily trip to the dog park provided exercise and fun stimulation. Sarah communicates promptly and thoroughly. She truly cares about my dog’s safety and wellbeing. We have booked a 2 week stay with Sarah this summer. We are very comfortable doing this knowing our dog is in such good hands.”


“Delightful person to leave our dog with, and we definitely hope to board him with her again in the future. We enjoyed the pictures and updates, and it seems like he had a great time. She even give him a bath when he got dirty!”


“Anthony was a wonderful host for our dog Robby. He watched him for 10 days and provided updates over that time. When we returned, we could see that Robby was content and clean. Anthony's mother mended his dog bed while we were gone - very sweet.”


“This was Dexter's second stay with Linda. As soon as we got to the house he ran into the backyard and never looked back. It was great knowing that Dexter was in a loving home and had the opportunity to play with lots of dogs while we were away. Thanks Linda!”


“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!”



“This is the second time we’ve used Ingrid to watch our Winnie. We are SO glad to have found her! She is so wonderful with Winnie, and treats her like she’s her own. Every time we pick Winnie up from her house, she’s happy & seems like she’s had a great time. Ingrid sends pictures of Winnie while we’re away, and is very responsive. We would 100% recommend her, and plan to use her the next time we need a sitter.”


About: I love the joy that dogs add to life and I’m thankful to have the experience in raising and loving on so many! Loving your pet as if it were my own would be priority. I know it can be stressful in finding good help that you can count on so that would be my promise to you. Message me for more details or questions! After recently losing my own dog, I realize a majority of my daily routine involved and was centered around his care. I miss the responsibility and adventures! I would care for your pet in the same way you care for them to reduce stress in environmental change. Love and attention would be what your pet experiences under my care.

About: I have experience aid medical and grooming any breeds. I do have so many patients for any pets. I always come up new ways to make sure they enjoy their fun games I work part time on weekdays so I am available certain holidays and weekends. If you have any questions or certain about your baby feel free left me a messages I have fenced yard and there is grooming room if your pet decides to get smelly even dirty coat. One my siblings does own 6 dogs if you choose to play date :)
Loving pet boarding sitters in your neighborhood
Search Results
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.




Kristen K.Star Sitter

“Major had another great time, seems he even met some new doggie pack friends 😀 love how much space he has to run around, always comes back tired, which is a great thing.”


Jaclyn S.
Star Sitter


“Jaclyn had all of her ducks in a row. My first time sitting with her and she answered all of my questions and asked really good questions of her own. I was comfortable that she has planned how to safely and comfortably keep new dogs at her house. Even if they’re of the nervous type like mine. She also kept me updated daily with messages and photos which we really appreciated. Thank you, Jaclyn, for taking such great care of Bini.”




Chris A.


“Chris, what an exceptional job. When I first met Chris, it was very obvious he was just excited to hangout with my pup. Dropping her off was simple and gave me a lot of confidence for Indys Stay. Chris sent me pictures during the entire 6 days he cared for Indy. Picking her up, they had already been out on a nice walk and it was obvious because she was very tired. I plan on using Chris again and would recommend anyone to entrust Chris with their Animal.”




Charity M.Star Sitter

“We couldn't be any happier with the care Juicy received from Charity. She was incredibly sweet, kind, and responsive, making us feel at ease leaving our furchild in her hands as we traveled. Juicy was treated like one of her own, and we appreciated how accommodating she was throughout the entire process. The pictures and videos were also a nice touch. Five stars without a doubt!”


Erin G.Star Sitter

“Great family! They gave me daily updates on Ranger and how he was doing. When I picked him up he seemed like he was having so much fun he didn’t want to leave!”


Maki M.Star Sitter

“I was looking for a place to board Sake that was a mid-point between my home to Bryce Mountain to go skiing. I found Maki who was on the way to the slopes. She was very accommodating when I forgot the dry food (Mom Brain), but luckily I brought enough wet food for Sake's meals. I appreciate they were very patient with Sake trying to sleep in her crate at night while I am attempting to crate train her. I was worried she might be howling most of the night, but surprisingly, Sake ended up napping inside her crate after we got home today. This is a new behavior for Sake which I am so happy to see!!!! This is a good sign that she is dreaming of all the fun walks and attention she got from Maki and her family. She shared photos and informed me on all of her walks, her desire to chase a squirrel, and when she peed, pooped, finished her meals, got several belly rubs and chilled at the house. I highly recommend you go to Maki whenever you need boarding. She is conveniently located on the way to the slopes. Upon pick up, her son was kind to carry the crate out to my car and place it in my trunk. I noticed that Sake's belongings were neatly folded, cleaned and organized inside the overnight bag. Sake will definitely return when I need to go back to the mountains for the weekend or day when I am not able to bring her with me. Thank you for taking good care of her. When I see Sake sleeping well after her visit from boarding, that is a positive sign that she had an awesome time with the family.”


Mallary P.

“We left our two dogs with Mallary for over a week. She took good care of them and sent pictures everyday. Thanks to her, we were able to enjoy our vacation knowing that the dogs were in good hands. The dogs were happy and healthy when we picked them up. They weren't in any hurry to leave and kept looking for Mallary's dogs, their new friends. It was so sweet. Thank you, Mallary! We will be back!”


khalida m.

“Khalida and her husband were very nice and took great care of Manolo. They took pictures and gave me daily updates. Thanks again for taking great care of Manolo!”


Abby R.

“Abby did a wonderful job watching our dog! We had a meet and greet the week prior that went great, her two dogs are sweet and playful and got along with ours well! I’m not sure our dog wanted to come home she was so happy there!!”


Audrey R.


“Audrey is amazing!!! She took great care of my two dogs while me and my family were out of the country for 9days. She is very knowledgeable and passionate about them. I recommend her and will contact her again in the next time we need her. Thanks Audrey! ?”


Carol D.

“Took awesome care of my dog. Would absolutely use again”


Briana J.

“Brianna was very attentive communicating with us and gave Apollo all the attention he loves. I will be using her services again :)”


Sarah J.Star Sitter

“Lots of TLC and a safe environment are top priorities when we select a dog sitter for our golden doodle. Sarah and her family all gave so much care and kindness to our pup. Frequent walks on her quiet street and a daily trip to the dog park provided exercise and fun stimulation. Sarah communicates promptly and thoroughly. She truly cares about my dog’s safety and wellbeing. We have booked a 2 week stay with Sarah this summer. We are very comfortable doing this knowing our dog is in such good hands.”


Sonja W.


“Delightful person to leave our dog with, and we definitely hope to board him with her again in the future. We enjoyed the pictures and updates, and it seems like he had a great time. She even give him a bath when he got dirty!”


Anthony B.

“Anthony was a wonderful host for our dog Robby. He watched him for 10 days and provided updates over that time. When we returned, we could see that Robby was content and clean. Anthony's mother mended his dog bed while we were gone - very sweet.”


Linda S.


“This was Dexter's second stay with Linda. As soon as we got to the house he ran into the backyard and never looked back. It was great knowing that Dexter was in a loving home and had the opportunity to play with lots of dogs while we were away. Thanks Linda!”


Allison B.

“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!”




Ingrid H.

“This is the second time we’ve used Ingrid to watch our Winnie. We are SO glad to have found her! She is so wonderful with Winnie, and treats her like she’s her own. Every time we pick Winnie up from her house, she’s happy & seems like she’s had a great time. Ingrid sends pictures of Winnie while we’re away, and is very responsive. We would 100% recommend her, and plan to use her the next time we need a sitter.”


Joanna S.
About: I love the joy that dogs add to life and I’m thankful to have the experience in raising and loving on so many! Loving your pet as if it were my own would be priority. I know it can be stressful in finding good help that you can count on so that would be my promise to you. Message me for more details or questions! After recently losing my own dog, I realize a majority of my daily routine involved and was centered around his care. I miss the responsibility and adventures! I would care for your pet in the same way you care for them to reduce stress in environmental change. Love and attention would be what your pet experiences under my care.


Marlene C.
About: I have experience aid medical and grooming any breeds. I do have so many patients for any pets. I always come up new ways to make sure they enjoy their fun games I work part time on weekdays so I am available certain holidays and weekends. If you have any questions or certain about your baby feel free left me a messages I have fenced yard and there is grooming room if your pet decides to get smelly even dirty coat. One my siblings does own 6 dogs if you choose to play date :)
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 pets2. Meet & Greet
Meet either virtually or in-person with a boarder to discuss the level of care needed for your pets while you’re away3. 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.
