Dog Boarding in Winchester

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

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
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1. Nichole

Loving Family w/ Large Fenced Yard

Winchester, VA, 22602

Dog Boarding, Doggy Day Care

"What an amazing experience it was. Our dog was loved and taken care of as if he belonged to her. Beautiful family that gave lots of love. Can’t say enough ab... (more)"

Confirmed availability
Christmas and New Year
2. Angela

Home full-time - play time everyday

Winchester, VA, 22601

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

"Angela was great, she keeps you updated and the house was nice and clean. Communication went well and it was easy going. Recommend and will use her for futur... (more)"

3. Anders

Stay home dad on 8+ acres of fun

Clear Brook, VA, 22624

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

"This was our first time leaving our dog with Anders. Anders was very kind and attentive. Our dog seemed very happy running around his big yard and playing wi... (more)"

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4. Linda

Dogs love coming to Auntie Linda's

Winchester, VA, 22602

Dog Boarding, Drop-In Visits, Doggy Day Care

"I am extremely happy with Linda and my experience with her as my dog sitter. It was obvious that she is a dog lover, I felt like my puppy was in very safe ... (more)"

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5. Meghan

Holbrook Hound Hotel!

Stephens city, VA, 22655

Dog Boarding, Drop-In Visits, Dog Walking

"Duke loved his stay with Meghan. He got to play a lot, go on walks, and had a nice fenced in yard to run around and play in. He was worn out when we got him ... (more)"

6. Conrad

Dogs are a man's best friend

Winchester, VA, 22602

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

"Conrad was quick to stay in touch throughout the stay/ask questions for my puppy's first sitting, and she loved his care. Great job and definitely recommend! (more)"

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7. Bridget

Home Full Time, Huge animal lover!

Winchester, VA, 22602

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

"Nana had a great time with Bridget. She has a new four-legged friend now and new two-legged friends for walks, pets, treats and all the good stuff she expect... (more)"

8. Brittany

SAHM with lots of cuddles to give!

Winchester, VA, 22602

Dog Boarding, Doggy Day Care

"Brittany was great! She was so good with Sebastian. I will definitely being him back to her (more)"

Confirmed availability
Christmas and New Year
9. Danielle

Love dogs, walks and playing catch

Winchester, VA, 22602

Dog Boarding, House Sitting, Doggy Day Care, Dog Walking

"Danielle took excellent care of my furr-baby over the long weekend that we were out of town. She kept in touch daily and sent pictures of walks and play time... (more)"

10. Jillian

Avid dog lover

Winchester, VA, 22602

Dog Boarding, Drop-In Visits, Dog Walking

"Jillian is absolutely great with our pets! She's loving, patient, and understanding, even with our pomeranian who had high anxiety. Would highly recommend he... (more)"

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11. Amelia

The best dog sitter ever!!

Winchester, VA, 22801

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

About: I love to play with dogs, take them on walks, and cuddle with them! I have been caring for dogs since I was 8 and I love nothing more than being wi... (more)

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12. Holly

Can work from home when sitting

Winchester, VA, 22601

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

About: I have had dogs to take care of my whole life and there’s no better pet! My dog, Annie, is a husky and is very friendly. She is four years old and ... (more)

Confirmed availability
Christmas and New Year
13. Jessica

I’ll run with your dog!

Winchester, VA, 22601

Dog Boarding, Drop-In Visits, Dog Walking

About: Hi! I have a passion for animals. I love spending time with dogs of all breeds and sizes. I will treat your dog like my own! I love to hike, run an... (more)

Confirmed availability
This weekend
14. Brianna

Flexible, active and dog-educated!

Winchester, VA, 22601

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

"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)"

15. Rich

End of Summer Blowout Rate!! $20!!

Winchester, VA, 22602

Dog Boarding, Doggy Day Care

"Rich is my neighbor. I am a Rover provider. When I was a Foster Mom two dogs, he adopted one. I've never seen a more loving or devoted pet-owner. On many occ... (more)"

16. Tawanda

Ms. Tawanda

Winchester, VA, 22601

Dog Boarding, Drop-In Visits, Dog Walking

About: As an animal lover I am seeking a position to utilize my genuine love for a member of your family. With the concern for their health, happiness, an... (more)

Confirmed availability
Christmas and New Year
17. Deborah

Doggy Slumber Party!?

winchester, VA, 22601

Dog Boarding

"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)"

18. Christopher

I love dogs and so do my kids..

Winchester, VA, 22601

Dog Boarding, House Sitting, Doggy Day Care, Dog Walking

About: I'm dependable responsible and caring. All i ark is that owners be sure to make sure their pet has food and blankets or dog bedding to sleep on. I ... (more)

19. Amber

Animal lover!

Winchester, VA, 22602

Dog Boarding, Drop-In Visits, Dog Walking

"Amber is amazing! She watched my seven month old lab mix at her home while I was gone for six days. She sent me daily updates and pictures and treated him li... (more)"

20. Madison

College student that loves Dogs

Winchester, VA, 22601

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

About: Will go for long walks and shower your dog with love and attention. I live by a park as well as a dog park so I can take them there. I also have f... (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.

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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.

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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.