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. Jeannette Verified Background Check

Home full time

Lexington, KY, 40509

Dog Boarding, Drop-In Visits, Doggy Day Care

"My dogs were happy and well taken care of. One of our dogs has high anxiety and isn't a fan of strangers but was able to relax with jeannette. (more)"

2. Megan Verified Background Check

All dogs welcome!

Winchester, KY, 40391

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

"Megan did an excellent job watching our four month old puppy! She made sure he was well taken care of with food, walks, training regiments, and plenty of pla... (more)"

3. Heather Verified Background CheckRover 101

Join the wolf pack!

Lexington, KY, 40516

Dog Boarding

"Heather and her family were great with my boys. I received photos daily and she was very accommodating with my busy schedule. We will definitely be using Hea... (more)"

Confirmed availability
Labor Day
4. John Verified Background CheckRover 101

Arf Bark n Bed Hamburg

Lexington, KY, 40509

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

"John was amazing with my dog. He treated her like family and sent me pictures and updates every day! His dog, Pixie, was so sweet and got along really well w... (more)"

5. Hagan Verified Background Check

I will treat you pet as my family

Winchester, KY, 40391

Dog Boarding, Drop-In Visits

About: I have taken care of boxers and pit bulls my whole life, I will treat your animal(s) as my own and make sure all there needs are taken care of, I h... (more)

6. Octavia Verified Background Check

Experienced Vet Assistant

Lexington, KY, 40516

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

"Octavia did a great job with our new pup! Quick to respond and very much exceeded our expectations. (more)"

7. Lindsey Verified Background Check

Treating them like family❤️

Winchester, KY, 40391

Dog Boarding, Doggy Day Care

About: I have a ton of experience caring for animals not only cats and dogs but also hamsters, gerbils and different reptiles. Growing up there was always... (more)

Confirmed availability
Labor Day
8. Marlize Verified Background CheckRover 101

Best puppy vacation destination!

Lexington, KY, 40509

Dog Boarding, Drop-In Visits, Dog Walking

"Marlize has a great facility for my dogs. They get to run within a 1 acre beautifully fenced yard away from the city but not too far out. She is a vet tech f... (more)"

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9. Nathaniel Verified Background Check

Best pet care in Central KY

Lexington, KY, 40515

Dog Boarding, Doggy Day Care

"Nathaniel was AMAZING with my Ellie. Was in a rut where I needed a sitter and he helped her feel comfortable and safe while he had her. He was very understan... (more)"

10. Gloria Verified Background Check

Eager to help!

Winchester, KY, 40391

Dog Boarding

"Gloria is fabulous! She has taken care of and groomed our little dog many times over the last few years. I never worry while our dog is in her care. She is v... (more)"

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11. Megan Verified Background Check

Let me love your dog for a while!

Lexington, KY, 40509

Dog Boarding, Drop-In Visits, Dog Walking

"Megan and her boys are so wonderful! They took great care of our Lab, Wick. She sent several pictures, and kept us updated throughout his stay. Wick came hom... (more)"

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12. Sarah Verified Background Check

Flexible hours, fully fenced yard

Southeastern Hills, Lexington, KY, 40517

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

"Sarah has watched my dogs multiple times over the years. Every time I drop them off I know they're in great hands. The dogs love going to her house! (more)"

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13. Lauren Verified Background Check

Unbound Dog Services

Mount Vernon-Hollywood-Montclair, Lexington, KY, 40508

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

"Lauren was a wonderful caregiver for my fur baby. Diesel loved his weekend stay with Lauren and did not experience the separation anxiety that usually occurs... (more)"

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14. Narissa Verified Enhanced Background Check

Active lifestyle

Kenawood-Rockwood, Lexington, KY, 40505

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

"Ganon had a blast with Narissa. I loved all the updates she kept giving me throughout the entire weekend too! She certainly cared for Ganon as if he were her... (more)"

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15. Micki Verified Background Check

We have a 30 acre farm-dog heaven

Paris, KY, 40361

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

"Great job! She made my sweet girl part of the family. We definitely will use her services again. Many thanks. (more)"

Confirmed availability
Labor Day
16. Anita Verified Background Check

Can your dog be my best friend too?

Duncan Park, Lexington, KY, 40508

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

"Anita was too die for, My baby hasn't seen such amazing hands since my own. I swear it. She kept Shawney for a week straight once and I knew I didn't have to... (more)"

17. Katy Verified Background Check

I will run and play with your dog!

Lexington, KY, 40514

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

"Katy took excellent care of my two dogs for two weeks. She sent me pictures and updates and didn't mind when I checked in with her. I think they had a bett... (more)"

18. Keegan Verified Background Check

Crazy Dog Mama

Lexington, KY, 40509

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

"I strongly recommend Keegan for pet care services without reservation. She is caring, conscientious, very competent, loves animals and has taken good care o... (more)"

19. Alexander Verified Background Check

Just a guy who loves animals.

Southeastern Hills, Lexington, KY, 40515

Dog Boarding, House Sitting, Doggy Day Care

About: I have taken care of pets since I was a kid. Even raising a few liters of puppies during highschool. And have taken care of most house pets. I am ... (more)

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20. Frances Verified Background Check

Lifelong Animal Lover

Chevy Chase-Ashland Park, Lexington, KY, 40502

Dog Boarding, Doggy Day Care, Dog Walking

"Frances was delightful! Took great care of Max... he was a happy guy when we picked him up. His tail was wagging and he appeared to be Frances’s guardian at ... (more)"


As dog lovers, we understand how difficult it can be to leave your dog when you have to head out of town. Luckily, you can find the perfect Winchester dog sitter in seconds on Rover.com. If you're looking for dog boarding while you're away, whether it's for one night or a whole month, you can find a dog sitter in Winchester, KY who meets your - and your dog's - needs. We manually review and approve every profile on our site, and we offer tools to help you make the right decision for your dog - including background checks and community reviews. We also offer educational opportunities and extra safety tools, such as the Protection Package. And we always recommend an in-person Meet & Greet so you can see that your sitter is the perfect fit for your dog. Rover is proud to be the nation's largest network of dog lovers for hire, and that includes offering pet boarding in Winchester, KY.

If you're the sort of person who likes to book services when you're out and about, you'll love the Rover dog boarding app. In minutes, you'll be able to view hundreds of experienced dog sitters no matter where you are, or re-book on-demand with your puppy's favorite dog sitter. You'll get to check in in real-time to see how your dog's day is going, with the photo updates feature from your dog sitter via the Rover dog boarding app. And if you hate carrying cash, or calculating tips, you'll love the Rover app's cashless payment feature which enables fast, secure payment of your dog sitter without money needing to change hands.

The cost of dog boarding in Winchester may surprise you - in a good way. That's because there's a dog sitter on Rover for nearly every price range and lifestyle. Curious about how much you can expect to pay for dog boarding on Rover? Check out our average dog boarding rates to get an idea before you start a conversation with an individual dog sitter.

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.

What if you're a dog lover who's looking for dog boarding jobs? You'll want to check out our information about how to become a dog sitter on Rover. We're always excited to add new dog sitters to our dog boarding service, and our application process makes it simple to get your own dog boarding business up and running. When you become a Rover dog sitter, you benefit from great features including premium pet insurance, a third party background check, and our cashless payment feature for ease and peace of mind. Why not apply today?