Pet Boarding Winchester
Find a loving Winchester pet sitter to watch your cat or dog overnight at your sitter’s home.
Over 649 pet parents in Winchester have booked pet boarding
Winchester, Find top rated pet boarding
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Chris and his family are always excellent. We love leaving our baby boy with them; they feel like family. It's another home for him to enjoy and snuggle in. We are grateful to Chris, Rob, Carla, and their new social kid, Milo, for making it such a wonderful place for our baby Boy to spend time and have fun. Thank you all for the warmth and care!”
“We are SO SO happy we found Kristen! We had a one night trial and our pup couldn’t have been happier. We then had her go back for a whole week while we were on vacation. It was wonderful because Kristen checked in when we asked for it, which was nice since we were on vacation. She was quick to respond and sent us some fun photos of our doggie having the time of her life. It is such a relief to feel like you can really trust the person taking care of your dog while you are away. We could tell she was happy to be there and Diddums will definitely be returning! :) THANK YOU!”
“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!”
“If you're ever looking for a place for your fur kids to stay while you go out of town, I highly recommend Laura. I have 2 neurotic cats; 1 has CH that does not like getting confined in crates/small place and the other is spicy/moody. The stay was short with a (somewhat) unusual request, but Laura took them all in stride and went the extra mile to look after Sam and Cloud. Definitely one of my best rover experience and would not hesitate to ask her again in the future.”
“Lauren, impressively on short notice, took my pup in for boarding and was remarkable with his care! I highly encourage anyone seeking pet assistance to consider Lauren for services & I plan to seek her services the next time my pup needs boarding.”
“Jessica was wonderful, I’m not sure my poodle missed me at all. She sent me regular updates, pictures and videos. Sometimes he was happily lap sitting. Sometimes she videoed him playing with toys her dog or interacting with her family. I was gone 10 days. I was happy to see him doing so well. He is a picky eater so I had sent cubed up chicken breast to mix with his food. When she ran out she cooked him another, which was going way above what I expected. I would definitely take my dog to Jessica again.”
“Super friendly couple that took great care of our Dicey, sending us updates and pictures to brighten our day while traveling. I highly recommend them for your pet sitting needs.”
“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.”
“Sarah was wonderful with Murphy and Mazi. She kept me updated with pictures, handled their medications carefully, and clearly treated them like part of the family. I really appreciated how flexible and accommodating she was with my schedule, including extending their stay by an extra day when my plans changed. I would absolutely trust Sarah with them again.”
About: I’ve been in the general field of caretaking for about 6 to 7 years. I was a full time nanny to a family of 7 children and 3 dogs for a few years before I married, and before that, I had multiple families for whom I watched their little ones, including the family dog/dogs. I also did some exclusive pet sitting apart from my previously mentioned work experience. I managed both kids and pets at once. I’ve gotten to know a variety of dog breeds. Growing up, we always had dogs. We’ve had a labradoodle, a few small mixed breeds, and a bernedoodle. Our bernedoodle, Rocco, I trained myself. He is the gentlest dog I’ve ever met and so smart. I taught fun tricks but also some useful ones like how to ring bells to indicate he needed to potty. I have loved being around dogs and having them in my life. We don’t currently have a dog since my two kids are young, so we can’t afford our own pup right now, although we certainly will get one in the future. That’s why I’m so excited to be able to provide other people’s dogs a warm and welcoming home away from home where they will be loved on and feel at ease. I’m a full time stay at home mom, so I’m almost always home. Apart from grocery shopping, minor errands, church on Sundays, or the rare trip to families, we are home all the time. Dogs that stay with us will have pretty much constant companionship and attention. We will be available for drop offs everyday except most of Sunday. Sunday evenings will be open though. Dogs that love a family environment will thrive here. We are usually up for the day around 7:00 am. My son loves dogs and will happily have a full conversation with them. He has grown up around many dogs because my mom has dogs and is a seasoned rover sitter herself. My husband works in the evenings so dogs will probably stay up and hang out with me as we unwind. We have a fenced in backyard so I can sit on our deck and let the dogs run, play, and potty easily and frequently. We live on a very quiet and friendly Cul-de-sac in the mountains of West Virginia, near Winchester. Dogs that come here will have a peaceful stay and have a lot of fun!
“Lauren was great with our dog Maggie! We left our our dog (7lbs) with Lauren for 7 days while we were traveling. Lauren was responsive with communication and was good about sending pictures of Maggie. Our sweet pup can be anxious and doesn’t do well in new environments but Lauren had a very sweet demeanor and nice home and I think Maggie became quite comfortable there. I would definitely leave our fur baby with her again!”
About: I provide a clean, cozy, and loving home where pets can feel safe, comfortable, and part of the family. Our fully fenced backyard offers plenty of space for supervised play, exercise, and fresh air, while the indoors is a calm, comfortable environment with lots of attention and affection. We also have two friendly, well-socialized dogs who enjoy the company of other pets and help create a welcoming atmosphere. Whether your pet loves to play, explore, or simply relax, they’ll receive personalized care, plenty of love, and the attention they deserve throughout their stay. I’m a full time stay in home mom, who will be home most of the time to provide potty breaks and will be able to be close to pets. I have a fenced back yard. And all areas of my home are gated. Your dog will be kept in a comfortable free space. I can provide a more personal crate if required.
“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!”
“THE BEST! Michelle and her son are the SWEETEST. So easy to talk to and very communicative. We are so happy we found Michelle . Unfortunately, our previous sitter can no longer watch dogs. So we have tried to find a sitter that matches her love and treated our girl like her own. Our doggo was even so sad when she got home. I'm sure she missed Michelle and her sweet son. She had such a great time being spoiled and playing all day.”
“We have had our dog now for a second time and we couldn’t be happier!!! Our dog has so much fun with her and enjoys a lot his stay with Michelle. She also constantly sent me updates with lots of pictures and videos! It was really a great experience booking with her so I highly recommend Michelle!”
“Alicia and her boys made my pups so comfortable, I wasn't sure they'd want to come home with me after the five day stay! She shared pictures and updates that warmed my heart and put my mind at ease for their first-ever stay away from home. I will definitely rebook with her in the future and highly, highly recommend her to others.”
“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.”
“Jordan was amazing. In her profile she mentions last-minute options & that saved our last minute trip. I'm new to Rover & expected people's availability was accurate but over a dozen people provided bad info. She accepted hours before we dropped our dog with her. She was kind & brought my dog on errands & Starbucks for a pup cup.😂 Her location is super convenient driving from Arlington to 81 on 66. She has a few children that loved playing with Opal. She didn't introduce her dog with ours which is fine. Would definitely reach out again if we go that way.”
The median cost per night for pet boarding in Winchester is $50
Pet parents share their Rover experiences - Winchester
Linda has been dog sitting me for quite awhile. I have had nothing but good experiences with her. She treats our dogs like they are her own. They get lots of attention and tummy rubs and are allowed on the furniture and in the bed at night, just like home. We have used Rover for a long time and of all the dog sitter we have had over the years Linda is our favorite!!
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.
Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.
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 sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
Meet local sitters who will treat your pets like family
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Popular requests for pet boarding - Winchester
Select a filter and find qualifying sitters offering pet boarding.Sitters in Winchester average 14 repeat pet boarding clients
FAQs for Pet Boarding - Winchester
Frequently asked questions about Rover
The average cost for Pet Boarding in Winchester on Rover is $38.85 per night (as of September 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Pet Boarding easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Pet Boarding. For more information on service fees, click here .
There are 334 sitters on Rover for Pet Boarding in Winchester. About 89% of Winchester sitters can respond to requests in under 60 minutes. Whether you’re planning ahead for holidays, need last-minute care, or need same-day coverage for an urgent trip, you can message multiple sitters at once to find available care.
Once you find the right match, you can arrange a Meet & Greet to ensure they are a perfect fit for your pet’s personality before confirming.
If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.
The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.
The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.
All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.
A Meet & Greet is a short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.
Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.
Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .
While each sitter sets their own vaccine requirements, staying up-to-date on your dog’s vaccines is the best way to be "boarding ready". Vaccinations help create a safe environment for all pets under a sitter’s care.
Many sitters in VA ask that dogs be up to date on core vaccines like the Canine Parvovirus, Canine Distemper, Canine Adenovirus, Bordetella, and Rabies. Cats may be required to have Feline Viral Rhinotracheitis and Rabies up to date.
By discussing your pet's health history early, you’re adding a layer of confidence for you and your sitter before the booking begins.
Emergency support is available by phone or email in English 24/7. When an incident occurs, we recommend that sitters contact our Trust & Safety team immediately so that they can connect your sitter with a board-certified veterinarian or offer other resources to help.
If a sitter needs to cancel at the last minute, Rover’s reservation protection means our team will work with you to find a suitable replacement as quickly as possible.
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