Pet Boarding Winchester
Find a loving Winchester pet sitter to watch your cat or dog overnight at your sitter’s home.
Over 650 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.
“Yogi enjoyed his stay. I like that there are options. Dogs can stay in the house. But if they are more comfortable outside, she has a deck with access to a fenced in grass area. Good communication. No problems.”
“Pamela was a pleasure to book with. She is responsive when I reached out with questions, gave regular updates, and gave our pup extra love and playtime with other pup/kitty friends. Will definitely be booking again!”
“I cannot thank Michelle and her family enough for watching Bella multiple times! Michelle is great with sending pictures, and keeping me updated as to how she is doing, Of course Bella loves to cuddle with the entire family as well. I would give more than 5 stars if I could!”
“My dogs Huey & Edward had a great time with Alicia & her boys. So happy to have found a great rover near me that I can trust with my dogs! She gave them great exercise & so much love.”
About: Ive taken care of and owned dogs for 20+yrs. I have alot of love to give an will love yours like they are my own. I am currently off for summer break and am available all days and hours. I live alone with my furbaby Koda,and I love all animals! I have a year old chocolate lab who loves new friends. I have a fenced in back yard and I have a crate if needed.
“We are so glad we found Lee and Cheryl! Our pup loves going to their house, we get great pictures and communication and I know he’s well cared for and happy while we’re away.”
“Ruth was so awesome and sweet! I could have not asked for a better person to watch my pup! My Dully was so happy and I got a bunch of photos of him having so much fun. Definitely recommend and will be going back to her every time☺️”
“Gabby is awesome! She took such loving care of our dog, offering updates and adorable photos throughout the stay. Came back to a happy and well-cared-for pet. Highly recommend Gabby!”
“Lauren provided excellent care for Bryce. She regularly sent photos and videos of him throughout his stay with her. Her yard is large and fenced in so plenty of space for your pup to zoom around. High recommend her for your dog sitting needs!”
“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!!”
“Chris is an amazing sitter and has a wonderful family. He took Jett on walking trails, fed him, and played with him. In addition, he sent pics throughout the stay. I could tell my doggy really enjoyed his time with Chris. I will be using him again in the future.”
“Amazing! I can’t say enough about how well she took care of our girls. I have already rebooked for our next trip. Not only does she treat the girls as family but she also works with training. We have a young pup so training has been out top priority. Highly recommended❤️❤️❤️”
“We had an awesome experience with Agnesa. She truly demonstrated to be a professional and knowledgeable dog sitter/trainer. We felt extremely comfortable leaving our 7 month old 60 pound labrador puppy under her care for the weekend. Agnesa kept us informed every day with multiple updates including pictures, videos, and observations about how our beloved puppy was doing during his stay. Our puppy is a high energy labrador and she managed to take great care of him while keeping him engaged in training sessions during his stay. She made sure our puppy and her dogs got along together and even took them on walks. We are completely grateful of her work and would definitely consider boarding our dog with her again. Highly recommended!”
“Laura was so great with Teddy! He loved playing with Gin!!! You can tell she really cares, and we felt totally comfortable leaving him with her. Selfishly, I almost don’t want to tell people how awesome she is 😉 We’d definitely book with her again if she’ll have him!”
“I HIGHLY recommend Tavin!!!! She is so sweet and I can tell she really loves animals and cares for them. I LOVED and appreciated all the adorable updates on how my fur baby was while I was away. I will definitely reach out to her when I need a puppy sitter from now on!!!”
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
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 Boarding - Winchester
Frequently asked questions about Rover
The average cost for Pet Boarding in Winchester on Rover is $38.85 per night (as of August 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 343 sitters on Rover for Pet Boarding in Winchester. About 88% 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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