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.

Confirmed availability: Memorial Day Weekend
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
111 reviews
47 repeat clients
from
$38
per night

shelby was awesome ! my puppy athena stayed the night there with another dog and had the best time. she made sure to send me pictures and videos of them playing and keep me updated. i definitely recommend her !

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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
83 reviews
34 repeat clients
from
$25
per night

My Emma was happy and safe. Jeannette was quick to respond and sent me pictures. This is so much better than a traditional boarding facility.

Confirmed availability: Memorial Day Weekend
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 awesome! Kronk had a great time with her, i’m glad he stayed with her. Definitely going to leave my dog again with Tonisha in the future when needed.

Confirmed availability: Memorial Day Weekend
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 was absolutely amazing with my puppy. He had never stayed away from me and she made him feel so comfortable and he had a great time with her pups. I will definitely be booking with her again!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Jennifer B.
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Sitter Profile Image: Jennifer B.
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6. 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 has taken care of our Labradoodle since moving here to Lexington 2 years ago. We have been very happy because our dog is happy when he stays with her and happy when he comes home. This trip we ran into travel delays because of the storms last night here in Kentucky. Jennifer was so accommodating with our travel delays. Thank you Jennifer for taken good care of our dog.

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Sitter Profile Image: Erin S.
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Sitter Profile Image: Erin S.
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7. 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
34 repeat clients
from
$35
per night

Erin was fantastic! She sent pictures and updated me and it was obvious Dudley was having a great time. My flight was delayed and she was completely understanding and happy to keep Dudley a few extra hours. I definitely plan to re-book with Erin! Highly recommended.

Sitter Profile Image: Micki O.
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Sitter Profile Image: Micki O.
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8. 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!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Sarah C.
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Sitter Profile Image: Sarah C.
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9. 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
3 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!

Sitter Profile Image: Cheyanne R.
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Sitter Profile Image: Cheyanne R.
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10. 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

I cannot say enough good things about Cheyanne! She has been watching my pets when I travel for the past couple years. She does an amazing job taking care of them and I never worry about leaving them in her care. Cheyanne has such a passion for animals and I know my pets enjoy getting to spend time with her. I would 100% recommend Cheyanne to anyone that’s looking for a pet sitter!

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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
19 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 .

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Sitter Profile Image: Kristin B.
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Sitter Profile Image: Kristin B.
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12. 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

It’s obvious that Kristin loves her 3 dogs, she took care of mine like it was one of her own. My dog has anxiety, Kristin sent me lots of updates and photos during the 2 day stay, and she takes wonderful pics! I wouldn’t hesitate to take my dog back to Kristin for a short visit or a longer stay.

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Sitter Profile Image: Bianca H.
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Sitter Profile Image: Bianca H.
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13. 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
26 reviews
8 repeat clients
from
$34
per night

Bianca incorporated Sophie into her pet family exercise and fun! Great communication, photos, and even a video! Sophie had the best time ever! Yes, we highly recommend Bianca!

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Sitter Profile Image: Sarah R.
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Sitter Profile Image: Sarah R.
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14. 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

Sarah was so kind and wonderful with my little dog Lucy. She sent pictures, updates, and even prepared special food for her when she wasn’t eating much. We loved Miss Sarah and will be using her again in the future!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Stacey U.
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Sitter Profile Image: Stacey U.
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15. Stacey U.

Rover 101
Artist/potter who works from home.
Lexington, KY, 40516
15.8 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
134 reviews
38 repeat clients
from
$39
per night

We needed to find someone to border our boy Henry while we visited Lexington and Stacey was our best choice - she didn’t let us down! Stacey took really good care of Henry and he quickly bonded with her. He had plenty of time outside in the yard and her home was well prepared for boarding. She seems to have a very natural way with dogs. Next time we visit Lexington we will definitely be calling on Stacey.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Brian C.
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Sitter Profile Image: Brian C.
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16. Brian C.

Caring reliable animal lover
Southeastern Hills, Lexington, KY, 40515
16.3 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
1 review
2 repeat clients
from
$25
per night

Communication and understanding and ability to accommodate on the fly was outstanding. Nova came back to me happy and relaxed. Would definitely recommend Brian to anyone and will definitely rebook.

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Sitter Profile Image: Dina J.
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Sitter Profile Image: Dina J.
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17. Dina J.

Animal lover seeks fun furry friend
Lexington, KY, 40509
14.5 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
80 reviews
23 repeat clients
from
$20
per night

Dina did an awesome job with my Lady. She kept me informed about what was going on with it. I will be recommending her to all my friends. Will definitely use her again.

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Sitter Profile Image: Madison M.
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Sitter Profile Image: Madison M.
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18. Madison M.

Hi there!
Lexington, KY, 40515
11.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
1 review
1 repeat client
from
$35
per night

About: Hi there! I absolutely love animals and enjoy taking care of them. I’ve been watching/taking care of dogs for around 10 years and I love it! I do have one dog of my own, but when I do book pets, she goes and stays with her grandparents, so your fur babies can have all my attention! I’m currently only doing Rover as a form of income since I plan to move to Montana in June, and have been preparing for that big move!! Because of this, I will be home almost all the time and your pups will have my full attention!! I have a fenced in backyard that is shaded by trees! All the dogs that I have watched seemed to love hanging out in the backyard!

Sitter Profile Image: Dana G.
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Sitter Profile Image: Dana G.
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19. 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.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Tania Z.
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Sitter Profile Image: Tania Z.
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20. Tania Z.

Rover 101
Fenced yard, dog door, comfy sofa's
Mount Vernon-Hollywood-Montclair, Lexington, KY, 40502
17.4 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
92 reviews
38 repeat clients
from
$42
per night

Tania was absolutely incredible! Teddy had stayed there for daycare in the past but this was the first time I’d ever left him overnight. Tania was so accommodating and sent lots of photos of him having a blast! Could not recommend her more, truly loves your pet like her own.

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  1. 1. Search

    Read verified reviews by dog parents like you and choose a sitter who’s a great match for you and your dogs
  2. 2. Meet & Greet

    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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    It doesn’t happen often, but if your dog sitter has to cancel, we’ll work with you to find a new sitter.

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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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