Pet Boarding Winchester
Find a loving Winchester pet sitter to watch your cat or dog overnight at your sitter’s home.
Over 387 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.
“Desirae was very responsive and accommodating. She sent daily messages and pictures of our dog. We appreciate Desirae’s support and excellent service. We’ll definitely book her again.”
“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.”
About: I have 3 dogs in my family and assist taking care of them on the daily. They are a mixture of breeds and big and small. I have also been dog sitting for various breeds and sizes for an extended amount of time! In addition to our three dogs, there is also a bunny in the family that I assist in caretaking for! I will be completing my Masters in Occupational Therapy this year and am in my last year of school at Ithaca College. I have a pretty flexible schedule during the week and open on most weekends. Looking for some puppy love and to help out when I can! I have a fenced in yard at home that we let my three dogs out in. We have three dogs with vastly different personalities so have ample experience in reading personalities and knowing boundaries for different types and how to step in and correct. Also with having a rabbit, I am experienced with different animal relationships and how they can interact.
About: I love dogs and can't wait to take care of your furry friend! I have a large home, plenty of room for your dog to stretch out. I have a yellow lab/golden retriever mix who is very friendly. I have a fenced yard (about half an acre) and another 9 acres of unfenced area. I work from home during the week, so will have plenty of time for walks, play-time, etc. I am good with all ages/sizes. I will ensure your dog is comfortable and safe, and has plenty of attention! I work from home so am always around to care for your pets! Will have plenty of potty breaks and play time. If I have to step out I can crate your pet or not, whichever you prefer. I have a fenced in yard I work from home so am always around to care for your pets! Will have plenty of potty breaks and play time. If I have to step out I can crate your pet or not, whichever you prefer.
“Lily had the best time during her stay with Marsha and Geary! They welcomed her like family, were attentive to her needs, and provided lots of love and play. We were grateful for daily updates with photos. It was evident at pick up how comfortable she was in their home. We will definitely book again in future!”
“This was our first time using Rover and it was a great experience. Emily is amazing. After meeting her, I knew immediately our Ray was in good hands. We loved the daily updates and pictures.”
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.❤️
“Kim was incredibly kind, honest, and genuinely interested in making sure our two dogs were happy during their stay. Our dogs have specific needs and one is over 100lbs. Kim’s home was perfect and safe for them. She has a fully fenced yard and they also had free-roam of her lovely, clean home. We live over an hour away, but Kim is more than worth the drive. I literally cannot say enough wonderful things about how well our dogs were cared for. She is the best of the best!”
“Tinnley was very accommodating to take care of our two pups. They enjoyed being there and had a great time with the our pups. I highly recommend Tinnley for your pet caring needs!”
About: I have been a vet assistant for 8 years, I now stay at home with my 1 year daughter and 4 dogs. We have chickens and a horse as well. We are big animal lovers of any kind. I'm a stay at home mom, I'm open all day and can come to your house or the pet can come to mine. We are very open to any schedule. We have a 6 foot private fence, and we have 4 dogs that are friendly with anyone and everyone. We also go to the dog park for more exercise with them as weather depends.
“Oliver seemed to have a good time with Pam and her family and their canine holiday guests. We were glad to receive photos of Oliver enjoying the Christmas tree and cuddling on the couch, along with periodic updates on his activities. Pam responded promptly to our initial query and to subsequent texts, and she even followed-up after we brought Oliver home. She seems to love dogs!”
About: I’m very caring and attentive to all animals and I am here to look after and play with them when you are unavailable. I have plenty of experience watching dogs, cats, and even reptiles on several different occasions for a few years now and I will never get tired of meeting new ones! I have a passionate love for animals and believe they deserve the best care possible. I’ve been looking for a job and came to the conclusion this is the best for me. Getting paid to care and tend to animals and even just hanging and chilling with them doesn’t even seem like a job to me but more like a fun time. As of right now, I have all the time in the world to look after pets and be their friend. Contact me whenever you need me! :) I live in a safe and friendly neighborhood. I do not have a fence but and perfectly fine taking dogs out on the leash for the bathroom or just for a walk. If you have any special requests or advice when you need me to look after them I am all ears and waiting for the details.
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 15 repeat pet boarding clients
FAQs for Pet Boarding - Winchester
Frequently asked questions about Rover
The average cost of Pet Boarding in Winchester is $37 per night as of November 2026. Most bookings cost between $28 and $56 per night. On Rover, 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 328 sitters on Rover for Pet Boarding in Winchester. About 90% 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 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 Meet & Greet.
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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