Dog Boarding in Winchester

Find a loving dog sitter to watch your dog overnight at your sitter's home.

1. Linda

Dogs love coming to Kamp Kelley

Winchester, VA, 22602

Dog Boarding

11 repeat clients

"Linda is an outstanding dog sitter! She has a way with your pets that no one else does! Our one dog who is very reserved and not affectionate with us, sat o... (more)"

2. Linda

I'll love your fur baby for you!!

Bunker Hill, WV, 25413

Dog Boarding

6 repeat clients

"Linda was a wonderful host for our dog Daisy. She sent us updates and a picture every day. We were a little worried about Daisy because she has some separati... (more)"

3. Kimi

I love the company of dogs

Berryville, VA, 22611

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

16 repeat clients

"Kimi was great with our two Holden's. Communication with her before and during was on point. She sent lots of pictures and let us know how the dogs were doin... (more)"

4. Megann and Ross

We Love Your Pets Like Our Own!

Winchester, VA, 22601

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

60 repeat clients

"Ross and Megann are wonderful and love taking care of animals! I feel so comfortable leaving my yorkie with them. My dog loves staying there! I'm so thankful... (more)"

5. Nichole

Homeschool family large fenced yard

Winchester, VA, 22602

Dog Boarding, Doggy Day Care

About: I have grown up with dogs always in the house from big Golden Retrievers to toy Pomeranians, even 4 different dogs at one time! Puppies were our li... (more)

6. Brianna

Flexible, active and dog-educated!

Winchester, VA, 22601

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

6 repeat clients

"Brianna did a wonderful job with or dog, Miller! She was very flexible on drop off and pick up times, and worked to accommodate our schedule. She also did a ... (more)"

7. Katherine

Camp for your buddy! Fenced Yard

Berryville, VA, 22611

Dog Boarding, Doggy Day Care

"Absolutely wonderful!! Katherine is very thorough and sent more than sufficient photos of Tank. I will use her for all my dog sitting requirements. (more)"

8. Elise

Certified Trained Fluff Magnet

Winchester, VA, 22601

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care

33 repeat clients

"Great experience! Annelise and her husband were very attentive to Daisy's needs. She does not do well boarding and needed a little more attention to feel... (more)"

9. Jessica

Pet friendly home w/ fenced in yard

Winchester, VA, 22601

Dog Boarding, House Sitting, Drop-In Visits

"Jess has watched my dog several times and she always does a great job! I have a timid dog, but he is excited to go to her house because she is so welcoming ... (more)"

Available this weekend
10. Rachel

5 Acre fenced yard- Home 4 days/wk

Berryville, VA, 22611

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

About: A walk a day keeps the vet away! It is an honor to be considered by you to play/walk with your furry best friend. I have always enjoyed getting to ... (more)

11. Barbara

I WFH so lots of play and snuggles

Berryville, VA, 22611

Dog Boarding, Doggy Day Care

3 repeat clients

"Barbara did an amazing job watching our yorkiepoo he came home a happy dog. I really appreciate that she was availabile to receive him on such short notice. ... (more)"

12. Terry

Must love dogs caretaker

Clear Brook, VA, 22624

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

"Terry's Pet Sitting is without question a wonderful resource! Her personal attention to each and every pet is exquisite! We used to take our pets to the kenn... (more)"

Confirmed President's Day Availability
13. Christa

Certified Vet Tech/CPR

WINCHESTER, VA, 22603

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

5 repeat clients

"Christa is an excellent sitter and I felt very comfortable leaving my dog with her. I got frequent updates and it was obvious that Daisy had a great time wi... (more)"

14. Elizabeth

Flexible schedule, fenced yard!

Winchester, VA, 22601

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: Animal lover living in Winchester City in a quiet neighborhood. I have a large fully fenced yard and a giant park in my backyard. My children (3,5 ... (more)

15. Krista

Stay-home mom - large fenced yard

Berryville, VA, 22611

Dog Boarding, Doggy Day Care

2 repeat clients

"Where to begin! My original sitter bailed on right before we had to leave. Krista was so flexible and accomodating and so responsive. She does have a puppy w... (more)"

16. Penny

I'm Home All Day With Your Dog

Cross Junction, VA, 22625

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

"Perfect dog sitting environment. Penny and family accepted Benny as their own. Thanks so much for loving our dog!!!! Professional and very responsive in comm... (more)"

17. Amber

Let me love your pups!

Winchester, VA, 22601

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

8 repeat clients

"Amber was amazing and flexible. Our puppy was well cared for. We will definitely use her again. (more)"

18. Heidi

Trusting and Caring Pet Sitter

Stephens City, VA, 22655

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Heidi was wonderful with Artemis. She kept in constant contact and updated me on how she was doing which was super wonderful. She has a fenced in back yard s... (more)"

19. Deborah

Doggy Slumber Party!?

winchester, VA, 22601

Dog Boarding, House Sitting

1 repeat client

"Deb was very helpful watching Calvin on such short notice on top of it being a holiday! She sent me pictures of Calvin along with updates of how he was getti... (more)"

20. Amber

Animal lover!

Winchester, VA, 22602

Dog Boarding, Drop-In Visits, Dog Walking

"Amber did a great job, very highly recommended (more)"


Rover.com is the simple, savvy way to find and book Winchester pet boarding. It's easy to find the perfect dog sitter - many sitters on Rover have a long history of dog sitting, and 95% of reviewed stays have received a perfect five-star rating. When you book dog boarding on Rover, your dog will enjoy a loving staycation in their sitter's home. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Every dog sitter in Winchester, VA has the option to complete a background check. Stays are booked on Rover every minute of every day, and more than 92% of the population lives within a short drive of one of our dog kennel alternatives. When you book [city name] dog boarding on Rover, your dog gets the loving care they deserve, and you get peace of mind.

Looking for an on-demand solution to your dog boarding needs when you're short on time? Then you'll love the Rover dog boarding app. The Rover app features hundreds of highly-rated, trustworthy dog sitters, and you can scroll through the options or simply re-hire your regular dog boarder in no time. Your dog sitter can share real-time photo updates via the Rover dog boarding app, and with the app's cashless payment feature you'll be able to compensate your dog sitter quickly and safely, with no need for cash, checks or tips.

The price of dog boarding in Winchester, VA might not be as much as you thought. Whatever your price range, you'll find a dog sitter on Rover for almost any budget. Interested in finding out what the typical Rover dog sitter expects as a dog boarding fee? Visit our average dog boarding rates report to see the general fees before checking out an individual dog sitter's hourly rates.

Are you a dog lover who wants to know more about how to turn your passion into profit? There's lots of opportunity to earn money with dog boarding in Middletown, NY. If you're not sure where to start, visit our page about how to become a dog sitter. We're always happy to include new dog sitters in our dog boarding service listings, and the simple application process means you can start your own dog boarding business in no time. We also take the hassle out when it comes to paperwork, because all our Rover dog sitters have access to helpful benefits including premium pet insurance and cashless payment feature, so you don't have to worry about getting paid on time. Why not apply today?

In other words, when you use Rover to find Winchester dog boarding services, your pet is given the best in loving care and hands-on attention, and you don't need to miss out on that just because life got in the way.