Dog Boarding in Winchester

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Sitter Profile Image: Madison A.
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Sitter Profile Image: Madison A.
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1. Madison A.

Reliable animal lover
Winchester, KY, 40391
4.8 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
16 reviews
5 repeat clients
from
$35
per night

Madison was amazing!!! Ranger is a very energetic pup and he had the best time with her and her dogs. She worked with all my requests and sent tons of pictures. I would give 10 stars if I could!!! I will definitely recommend her.

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Sitter Profile Image: Shelby B.
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Sitter Profile Image: Shelby B.
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2. Shelby B.

Unleashing Your Pup’s Potential!
Lexington, KY, 40509
12.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
108 reviews
47 repeat clients
from
$38
per night

Shelby was awesome, this was Bams first stay with her and definitely not the last. Bam stayed with Shelby for the weekend and sent me pictures throughout the time. This gave me peace of mind as i was fearful his anxiety would kick in. In all the pictures sent Bam looked like he was having a great time. I would recommend Shelby and her family to anyone looking for a sitter!

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Sitter Profile Image: Jeannette A.
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Sitter Profile Image: Jeannette A.
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3. Jeannette A.

Home full time
Lexington, KY, 40509
11.6 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
82 reviews
34 repeat clients
from
$25
per night

Jeanette is great! She took such good care of our senior girl, Mollie. She kept us updated and we could tell that Mollie was being well cared for and receiving lots of attention. We were able to relax and enjoy our vacation knowing she was in good hands. We will definitely be using Jeanette again!

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Sitter Profile Image: Tonisha T.
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Sitter Profile Image: Tonisha T.
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4. Tonisha T.

I Love My Fur Babies
Lexington, KY, 40515
14.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
88 reviews
38 repeat clients
from
$34
per night

Tonisha was very quick to respond and was very comfortable with our two dogs. She sent lots of pics throughout the weekend which was appreciated.

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Sitter Profile Image: Sarah W.
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Sitter Profile Image: Sarah W.
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5. Sarah W.

Welcoming all ages and sizes
Richmond, KY, 40475
17.0 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
46 reviews
17 repeat clients
from
$25
per night

Sarah watched Sarge for me during Thanksgiving week, and it was a lot of firsts for Sarge, who is a very, very anxious boy. I felt like I was honest with his behavioral issues upfront, but there were also a lot of unknowns. It was his first time being away from me for a whole week, and in an unfamiliar environment for him. I think the unknowns made it difficult for both Sarge and Sarah, but I think Sarah did the best she could have done.

Sitter Profile Image: Micki O.
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Sitter Profile Image: Micki O.
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6. Micki O.

We have a 80 acre farm-dog heaven
Paris, KY, 40361
16.9 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
23 reviews
16 repeat clients
from
$40
per night

I was a little worried about how Buckeye would do because he does not socialize a lot. He was a little nervous at 1st but quickly got to know the other dogs and had so much fun!! Micki was great and sent me pictures of how he was settling in on the 1st day when I was really worrying about him. She is extremely comfortable around animals and I am so glad to know there's a great place to take Buckeye whenever I need to leave town!

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Sitter Profile Image: Jennifer B.
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Sitter Profile Image: Jennifer B.
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7. Jennifer B.

Rover 101
Your Pet's Home Away From Home
Lexington, KY, 40515
15.1 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
86 reviews
44 repeat clients
from
$35
per night

Jennifer was so great! She provided regular updates and best of all great pics of Jessie and her playmates. This was Jessie’s first time from the family members. I was a little concerned at first about how Jessie would react. My fears were quickly erased and I now know Jennifer provides a great atmosphere for Jessie to deal with her separation from her family. I would greatly recommend Jennifer and will use her every time we need a sitter for Jessie! She earned and deserves a five star rating.

Sitter Profile Image: Bianca G.
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Sitter Profile Image: Bianca G.
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8. Bianca G.

Vet tech waiting to meet your pet!
lexington, KY, 40515
13.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
8 reviews
2 repeat clients
from
$25
per night

Bianca took such great care of my sweet dog Grace! I felt comfortable and confident booking Bianca because she knows a lot about dogs and animals in general. I love that my normally shy puppy felt super social and relaxed with Bianca and her family. It feels good to know I have a safe second home to leave my Grace if I ever need it!

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Sitter Profile Image: Erin S.
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Sitter Profile Image: Erin S.
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9. Erin S.

Fun, dog-loving home!!
Lexington, KY, 40515
16.0 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
78 reviews
33 repeat clients
from
$35
per night

Erin was the perfect sitter for our puppy. She checked in with us while we were gone and it was easy to coordinate with her for the drop off/pick up. It was also nice knowing Erin would be home to watch our puppy, since this was the first time we'd left her for an extended period of time. Erin's kids and dog were an added bonus, since we knew Maggie would get plenty of attention and exercise. Maggie came home happy and tired, which we greatly appreciated. Would readily book with Erin again.

Sitter Profile Image: Dana G.
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Sitter Profile Image: Dana G.
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10. Dana G.

Dependable, Conscientious, Kind
Castlewood Park, Lexington, KY, 40505
16.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
5 reviews
3 repeat clients
from
$25
per night

Excellent boarder and home! Dana & Dove were great! Pups were loved and cared for very well. Lovely fenced in back yard in quiet neighborhood. Their pup Arrow made the bestest of friends with my two. Consistent communication, updates pictures. Easy to work with for pickup and drop off. Highly recommend. I would use again.

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Sitter Profile Image: Kath & Jordan R.
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Sitter Profile Image: Kath & Jordan R.
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11. Kath & Jordan R.

Animal lovers w/ large backyard!
Duncan Park, Lexington, KY, 40508
17.0 mi. away
Boarding, Drop-In Visits, Dog Walking
5.0 out of 5 stars
18 reviews
9 repeat clients
from
$35
per night

The communication, photos, and care have been great. We can trust that our dogs will come home happy, which is especially important for our older anxious girl. I’m pretty sure our girls are just as happy and comfortable at their house as they are ours .

Sitter Profile Image: Cheyanne R.
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Sitter Profile Image: Cheyanne R.
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12. Cheyanne R.

PreVet student & vet tech
Winchester, KY, 40391
2.8 mi. away
Boarding, Drop-In Visits, Doggy Day Care
5.0 out of 5 stars
13 reviews
3 repeat clients
from
$55
per night

Cheyanne is a fabulous pet sitter. She has taken care of my dogs, cats, and chickens for years. They are always happy and healthy when we get back. The dogs remember her and are ecstatic when she comes to watch them. She is honest, trustworthy, and reliable. I cannot recommend Cheyanne enough for pet sitting! She is a blessing for my pets.

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Sitter Profile Image: Sarah R.
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Sitter Profile Image: Sarah R.
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13. Sarah R.

Fur Baby Fun, One Dog At A Time!
Lexington, KY, 40515
17.5 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
23 reviews
6 repeat clients
from
$40
per night

Highly, highly recommend Sarah!! She made me feel so comfortable all week while she watched him. Her communication and service was amazing! Several pics and updates daily, and our boy seemed so happy, we will most definitely use her again the next time when we need someone to watch our sweet boy!

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Sitter Profile Image: Bianca H.
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Sitter Profile Image: Bianca H.
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14. Bianca H.

5 Star, Budget Friendly ☀️
Idle Hour, Lexington, KY, 40517
15.0 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
25 reviews
6 repeat clients
from
$34
per night

Bianca is such a kind sitter! She responded and booked quickly when we needed to travel to the area last minute. She communicated well and sent pictures and videos. Jacob came back to us exhausted from playing and happy! Will definitely use her services again, when we are in the area!

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Sitter Profile Image: Bridget W.
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Sitter Profile Image: Bridget W.
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15. Bridget W.

Ready for a doggone good time!
Lexington, KY, 40509
12.1 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
6 reviews
1 repeat client
from
$40
per night

Bridget was wonderful for an overnight stay for Shelby. She was very communicative and sent many pictures and videos of her playing with and snuggling with Shelby. I would 1000% book with Bridget for any dog sitting needs!

Sitter Profile Image: Sarah C.
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Sitter Profile Image: Sarah C.
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16. Sarah C.

Happy pets = happy life
Clay City, KY, 40312
13.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
8 reviews
2 repeat clients
from
$25
per night

What a great sitter! They took my dog while we were in Brazil for two weeks. She sent photos and our dog seemed so happy. She even schedule and took her to a groomer since she need it so bad and I didn’t have the time to take her. Lovely experience. Book with her!

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Sitter Profile Image: Kristin B.
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Sitter Profile Image: Kristin B.
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17. Kristin B.

I’ll treat them like one of my own!
Mount sterling, KY, 40353
16.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
12 reviews
1 repeat client
from
$30
per night

Mrs. Becker was so accommodating to cole! He was very well taken care of and made some great friends with her pups. Mrs. Becker is a person you can trust with your beloved pets, she will make sure they feel comfortable, safe, and have a fun time. My cole did not want to leave! Thank you for giving cole an amazing experience while in your care!

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Sitter Profile Image: Stephanie N.
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Sitter Profile Image: Stephanie N.
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18. Stephanie N.

Play time is a must!!!
Idle Hour, Lexington, KY, 40509
14.5 mi. away
Boarding, Drop-In Visits, Dog Walking
5.0 out of 5 stars
18 reviews
1 repeat client
from
$37
per night

She was amazing and did such a great job with my pup!! Was willing to keep her an extra day to help me out, was so flexible and even sent my pup home with a gift bag!!!

Sitter Profile Image: Marlize V.
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Sitter Profile Image: Marlize V.
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19. Marlize V.

Rover 101
Best puppy vacation destination!
Lexington, KY, 40509
10.5 mi. away
Boarding
5.0 out of 5 stars
133 reviews
111 repeat clients
from
$35
per night

Marlize was great! She has a huge yard for the dogs to play with and they had lots of fun. She did have several other dogs staying with her at the same time as ours, but I think Lexi and Thor still got enough attention from her and had fun playing with the other dogs. She sent us several pictures of the dogs and kept good communication from before booking through picking up our dogs. I recommend!

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Sitter Profile Image: Cheyenne C.
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Sitter Profile Image: Cheyenne C.
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20. Cheyenne C.

Your pets home away from home 💕
Richmond, KY, 40475
14.4 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
23 reviews
8 repeat clients
from
$50
per night

Can't rave enough about this Rover. Pups are always so well taken care of! Truly their home away from home with the added benefit of furry buddies to play with. Cheyenne is super flexible willing to work with your needs, communicates promptly, and handles all aspects of the pups. Highly recommend.

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  1. 1. Search

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    Meet either virtually or in-person with a sitter to discuss the level of care needed for your dogs while you’re away
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Why choose Rover?

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Winchester Dog Boarding ratings

Overall Rating:
4.9 out of 5 stars

Dog boarders in Winchester are rated on average 4.9 out of 5 stars based on 51 reviews.


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?

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