Pet Boarding Winchester
Find a loving Winchester pet sitter to watch your cat or dog overnight at your sitter’s home.
Over 626 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.
“This is our second time using Erin. We rearranged our schedule a bit to accommodate her because I was more comfortable using her again than other sitters. I am nervous about leaving my little Lucy with someone because she is pretty used to being home with someone all day. With Erin, she or another family member is home with the dog most if not all the time. She also sends lots of pics and updates which is such a comfort when you are stressed about leaving your dog. My pup seemed vey content and got lots of attention! Would not hesitate to book Erin again!”
“Whitney was incredible good with my little one. She took care of him very well when I was sick. And Tokyo had a great time with her dog Feather. She sent me lots of pictures and lmk all the time of how was my dog, and I appreciate that very much. Thank you Whitney!!!”
“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!”
“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.”
“Lauren was absolutely amazing with our pup!! I couldn't recommend her more!! She is SO kind and caring. I could tell from the moment we had a meet and greet with her and her pups. She provided us daily updates on our pup and treats your pets just as she does her own. I was so relieved to find someone that I can trust our beloved furbaby with from now on. I was kind of upset that my pup wasn't more excited to come home, but that's just a reflection of the good time she had on her little vacay!! 🤣 Highly recommend Lauren for all your fur baby care!!”
“This was the best rover experience I’ve had. We felt completely comfortable leaving our dog with Lauren and her sweet family. We received pics of Mia having the time of her life. So caring in her updates and we loved knowing that Mia was getting plenty of outdoor time, love, and attention!! Thank you so much !!!”
“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!”
“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.”
About: I care for every pet as if they were my own, making sure they always feel safe, comfortable and loved. I spend quality time playing with them, giving plenty of attention, affection, and reassurance. Daily walks are a favorite part of my routine, allowing pets to stay active, happy, and relaxed. I also gently reinforce basic training and good manners to provide consistency and positive structure. My goal is to create a calm, loving environment where pets feel at home and owners feel complete peace of mind. Also a very great pet chef if needed. Available for house sitting or dog walking on weekends from Friday afternoon through Monday afternoon. Perfect for worry free weekend getaways! So plan your weekend trip and leave you fur babies with me! I have a fenced in backyard and two dogs of my own that would loved to keep your dogs company! My dogs love playing with balls and taking naps (dog crates if needed).
“They took wonderful care of our dog! They took her on field trips and adventures. They provided pictures and videos and were completely accommodating to our schedule and our dogs needs. Sammy had the best time and came home happy, healthy and tired! We felt completely at ease with them and their dog. Beautiful property for the dog to spend a weekend and we will happily use them again. Wonderful care of our dog without a worry! Thank you!”
“Tetiana did a great job communicating with me and providing prompt updates regarding my dog’s stay with her. I felt she provided a comfortable environment and appreciated her doing a meet and greet before I confirmed the stay. Would definitely be comfortable with my dog staying with her again.”
About: Hi! I’m Hope, a lifelong dog lover and experienced pet sitter offering in home dog boarding in a calm, family setting. I’m a stay at home mom to my two year old, so your dog will have constant supervision, attention, and care throughout the day. Our home is peaceful, loving, and ideal for dogs who enjoy being part of a family environment. We’re lucky to have a beautiful setup for pups: a fenced front yard/garden for safe outdoor time, plus an acre of land and nearby dog friendly trails for walks, sniffing, and exploring. Whether your dog loves playtime or prefers a slower pace, I tailor care to their needs and routine. Because I have a young child, I do require that all dogs are comfortable around children. Your dog will be treated like one of our own with plenty of love, structure, and attention so they feel safe, relaxed, and at home while you’re away. I’d love to meet you and your pup! Pet care naturally fits into my daily routine since I’m a stay-at-home mom and home throughout the day. Your dog will be part of our everyday rhythm—morning outdoor time, walks, play, rest, and evening wind-down. Because I’m home most of the time, I’m able to provide consistent supervision, attention, and care without long gaps. Throughout the week, I keep a steady routine while also adjusting to each dog’s needs, energy level, and schedule. My goal is to create a calm, predictable environment where your dog feels comfortable and cared for like part of the family. I send lots of updates and pictures and follow all care instructions carefully! I want you to feel comfortable with your pet in my care!
“Autumn was outstanding with Annie and kept me well informed with pictures and videos. Autumn has been a great communicator throughout the process and really made Annie feel at home.”
The median cost per night for pet boarding in Winchester is $50
Pet parents share their Rover experiences - Winchester
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.
How Rover works
1. Search
Browse profiles of sitters near you who offer pet boarding2. Meet & Greet
Schedule a free in-person Meet & Greet to find the perfect fit3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
Popular requests near you
Select a filter and find qualifying Winchester sitters!Sitters in Winchester average 14 repeat pet boarding clients
FAQs for Dog Boarding - Winchester
Frequently asked questions about Rover
The average cost for Pet Boarding in Winchester on Rover is $38.85 per night (as of June 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 331 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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