Pet Boarding Winchester
Find a loving Winchester pet sitter to watch your cat or dog overnight at your sitter’s home.
Over 654 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.
“As always I was able to enjoy my time away knowing that Sampson was in the best care. Ashley even took the most adorable Christmas pictures and had them printed out for me upon my return.”
“Christina was wonderful in taking care of Lilo. She attended well to her needs and gave her extra treats in spoiling her. She communicated well and gave me updates of Lilo on a daily basis and throughout the day.”
“Leah was just fantastic! I had a situation arise that precipitated the need to find someplace for my two boys a.s.a.p. and I am so thankful she was available. She treated them like her own, and they got along well with her two little fur babies too. They must've had a LOT of fun pn her beautiful property because they basically slept for the next 24 hours. So happy to have found Leah and it's great that she is so close too.”
About: I enjoy taking loving care of animals! I’m loving, kind, patient and passionate about their happiness. I’m an avid runner/walker 🏃♀️ and enjoy being outside with animals. I’ve had for dogs for about 15 years and cats all my life. I’ll take wonderful care of your pets of any age and I’m willing to work with puppies and kittens as well as older dogs and cats with special needs & everyone in between.🦮🐕🦺🐾🐈🐈⬛ Pets are my passion! I’m a full time pet sitter so I have time and flexibility for pet checks, feedings, playtime, snuggles as well as short and long distance walks! I can even pick up your pet’s food, treats, toys & meds!🦮🚶🏼♀️☀️🌳🏡 I’m dedicated, responsible and reliable and will carefully follow all your instructions to provide excellent and loving care for your pet(s) as if they were my own. I live in Berryville so I’m close by and available when you can’t be home.🏡 A portion of my income is donated to The Clarke County Animal Shelter.🐈🐕🦺 By giving your pets the care, affection, attention and exercise they need, I love what I do, and I do what I love.❤️
“Poppy loves Heidi and you can tell that Heidi loves her! Not only does Heidi give excellent care but she is flexible when we need to adjust our schedule! I cannot recommend Heidi highly enough!!”
About: I have pet been pet sitting for the last 5 years. Friends and family. I am good with all types of dogs. I can adapt to whatever the dog needs. I currently work Full time. I can talk care of the animals in the morning and after 4pm. I work Saturday morning not very often. On weekends I can check on animals 3 to 4 times as needed I do have a nice backyard with privacy. We have a tether attached to a deck. Lots of running / laying on a deck room. Inside my house is clean and pet friendly
“I had no worries while my pup was with Emily. She was super responsive and sent a bunch of pictures; it was reassuring knowing my fur baby was cared for so well while I was on vacation. She checked all my boxes, and I would use her again for sure!”
“Addie had a great visit with Sheila and Timothy for the 5 days we were traveling. This was our first time boarding her here as we recently moved into the area. Great communication and flexibility with our schedule that included cold and snowy conditions along with airline schedules. Thanks!”
About: I am a dependable and compassionate pet caregiver with hands-on experience caring for dogs and other household pets. I understand that every animal has its own personality and needs, so I take the time to build trust while providing attentive, personalized care. My experience includes feeding, walking, administering medications when needed, cleaning up after pets, providing companionship, and maintaining consistent routines to help them feel comfortable and secure. I am proud of my commitment to treating every pet like family. I pay close attention to behavior, energy levels, and overall well-being so I can quickly notice any changes that may need attention. I communicate regularly with pet owners, provide updates and photos, and always strive to give them peace of mind while they’re away. I am patient, reliable, and genuinely enjoy spending time with animals. Whether caring for energetic puppies, senior pets, or shy animals that need extra patience, I provide loving, responsible care that keeps pets happy, healthy, and safe. I work from home with generous breaks. While my schedule is 9-5, I wake early to go on walks in my neighborhood, and my work day includes 1.5 hours of breaks. After work is much like “before work”. A pet would work perfectly in this schedule I have a 3 story townhome and garage! I recently installed a fence! I will keep the pet entertained with fetch, and other stimulating games and puzzles
The median cost per night for pet boarding in Winchester is $50
Pet parents share their Rover experiences - Winchester
Kristina, her husband, and their dog Gorgi were amazing hosts to our sweet girl, Winnie. They made her feel right at home. She was taken on walks many times a day, got extra snuggle time and we received many photos throughout the time of her stay. Kristina was so kind to fill us in on how Winnie was adjusting as it was her first time in their home. It put our minds at ease knowing that she was so loved and cared for. We look forward to more play dates and stays in the future.
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.
Nicky and Bruce took our pups in and made them a part of their family. We were able to leave the dogs with them and not worry one single moment while we were gone. Nicky sent lots of pictures and videos and updates. The dogs enjoyed their "vacation" as much as we did! 😊
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.
How to book pet boarding
1. Search
Browse profiles of sitters near you who offer pet boarding.
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit.
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform.
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 of Pet Boarding in Winchester on Rover is $39 per night as of October 2026. Most bookings cost between $30 and $56 per night. sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
There are 330 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 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 , which provides up to 25,000 in eligible veterinary care reimbursement.
A Meet & Greet is a casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.
Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first .
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 .
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.
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, means our team will work with you to find a suitable replacement as quickly as possible.
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