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. Kelly

Fenced in yard & close to dog park

Lexington, KY, 40509

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

"Thanks for entertaining our Harvey this weekend. You guys are so loving and caring. We count ourselves fortunate to have your Services. FIVE STARS for sure! (more)"

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2. Jeannette

Home full time

Lexington, KY, 40509

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

"Jeannette kept my 2 dogs for 10 days while I was on vacation. She was able to accommodate me with fairly short notice when my previous sitter cancelled. Norm... (more)"

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3. Glenn

Where your Pet is our Pet!

Lexington, KY, 40509

Dog Boarding, House Sitting, Dog Walking

"Glen did an awesome job, as always. Not only does he take terrific care of our dog, he is such a considerate human being, dropping off our dog and turning on... (more)"

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4. Natalie

Weekend Puppy Getaway

Lexington, KY, 40509

Dog Boarding, Drop-In Visits, Dog Walking

About: I have been a dog lover all my life and have Sadie, a 5 year old chocolate lab, at home. We are always playing fetch and running around in my fence... (more)

Confirmed availability
Christmas and New Year
5. Marlize

Best puppy vacation destination!

Lexington, KY, 40509

Dog Boarding, Drop-In Visits, Dog Walking

"My girl had a BLAST! Marlize sent pictures all weekend and was always available. And the added bonus: I had a VERY sleepy dog when we got home. We will def... (more)"

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6. Jordan

Home full time-medium fenced yard

Lexington, KY, 40509

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

"Jordan is the best! Anytime I am away she watches my dog Julep. Julep loves her Aunt Jor more than anyone and gets so excited when she sees her. She talks he... (more)"

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7. Chelsea

Super flexible and friendly!

Lexington, KY, 40509

Dog Boarding, Doggy Day Care

"Amber loved her stay. Chelsea keep me up dated on how things were going each day with text and pics. I liked that Amber had a nice big yard to run and play ... (more)"

Confirmed availability
Christmas and New Year
8. Katie

Almost vet who loves to walk/run!

Paris, KY, 40361

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

"Katie is very knowledgeable about the care of animals being a vet student. I have felt completely comfortable with her watching my cats (and they are like my... (more)"

9. Derek

Tippy taps welcome!!

Lexington, KY, 40509

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

"Very reliable and trustworthy. On time and professional when it comes to service. Positive attitude during all interactions. My dogs were drawn to him from t... (more)"

Confirmed availability
Christmas and New Year
10. Eleanor

50 fenced in acres of farm life

Paris, KY, 40361

Dog Boarding, Doggy Day Care

"The absolute best with my dog! She has a great, fenced in property for the the exercise my dog needs and I always get pictures with updates on how she’s doin... (more)"

11. Jodie

My dogs are my family

Lexington, KY, 40509

Dog Boarding, Doggy Day Care

"Jodie was great with Abraham! He seemed right at home when he stayed the weekend with Jodie! He walked right in on the first day as if he had known Jodie his... (more)"

12. Heather

Join the wolf pack!

Lexington, KY, 40516

Dog Boarding, Doggy Day Care

"Heather watched my two dogs while we were on vacation over the New Year holiday. Heather was wonderful. We always have a difficult time finding someone to wa... (more)"

Confirmed availability
Christmas and New Year
13. Jimmy

Love dog walking❤️

Lexington, KY, 40509

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

About: I have cared for dogs since I was 12 years old for my neighbors, and it became something I loved doing! I currently have 5 dogs, that are very happ... (more)

14. Alyssa

Flexible pet sitter

winchester, KY, 40391

Dog Boarding, Drop-In Visits, Doggy Day Care

About: Hello my name is Alyssa, and I have over 10 years of pet care experience. I have loved dogs ever since I was little. In my house I have one cat and... (more)

15. Kayla

Weekend dog care. Fenced yard.

Lexington, KY, 40509

Dog Boarding, Doggy Day Care

About: I am the owner of a 1 year old female golden retriever, Millie. Millie is spayed, up to date on vaccines and loves other dogs. I will be providing ... (more)

16. Cassidy

TLC fresh from the farm

Winchester, KY, 40391

Dog Boarding

"I’ve known Cassidy for sometime now and her passion and love for animals is unbelievable. Currently having two cats two dogs and two bunny’s, each animal is ... (more)"

17. Jen

Friendly animal loving sitter

Lexington , KY, 40516

Dog Boarding

"Jen has a wide variety of experience with dogs of all temperaments and sizes. She loves animals and does a great job taking care of them! (more)"

18. Lauren

I love my pups, let me love yours!

Winchester, KY, 40391

Dog Boarding, Drop-In Visits, Doggy Day Care

About: Dog lover since birth. I am a registered nurse from Tuesday-Friday and available to care for your doggies on the weekends and during the week. My w... (more)

Confirmed availability
Christmas and New Year
19. Penelope

Home full time. Long walks or hikes

Lexington, KY, 40509

Dog Boarding, Doggy Day Care

"I have known Penelope for 40 years and she is one of the most caring people I have ever seen. She has been a dog lover and owner as long as I can remember. ... (more)"

20. Cierra

I'll walk your dog around

Winchester, KY, 40391

Dog Boarding, House Sitting, Doggy Day Care

About: Very nice , pets love me and I love pets I am willing to bond and care for dogs as if they were my own , I will not hurt or mistreat your pet . Any... (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?