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
108 reviews
47 repeat clients
from
$38
per night

I was Satisfied with Sugars Stay as awlways. I don’t have to Worry about my Sugar when I am Out Of Town. She Deserves more than 5 Stars. Thanks again for Everything

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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

Jeannette kept our 2 dogs for 10 days and they had the best time! They were well cared for, had plenty of room to play, and Jeannette sent me plenty of updates/pictures and quickly responded to my texts. I highly recommend Jeannette!

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 is great. I boarded my two dogs at her house for two days and she was very responsive and flexible before and during their stay. When I met her in person she was very kind and professional, and my dogs liked her right away. She sent multiple picture updates of my dogs outside playing or on walks which helped put me at ease. She is clearly very experienced with dogs and had no trouble handling my powerful Cane Corso or keeping my sneaky French Bulldog in line. My dogs were absolutely exhausted when they came home which tells me that they had a great time. I recommend Tonisha!

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Sitter Profile Image: Erin S.
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Sitter Profile Image: Erin S.
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5. 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

Absolutely perfect sitter for my little dog. He's a puppy and needs individualized attention and care. Erin and her family are able to provide loads of it!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Sarah W.
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Sitter Profile Image: Sarah W.
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6. 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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7. 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: Jennifer B.
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Sitter Profile Image: Jennifer B.
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8. 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 great! She made my older dog Ollie feel right at home hanging out on her couch. She helped me feel at ease with updates and pictures. Will definitely be booking with her again and would recommend her to anyone!

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

My two pups were wonderfully taken care of by Sarah (and her husband). I received pictures during their stay and emails with comments about their activities. Secure fenced yard gave me an additional sense of comfort in their stay. Will look to schedule again for a future trip.

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Sitter Profile Image: Kath & Jordan R.
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Sitter Profile Image: Kath & Jordan R.
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10. 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 .

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Bianca H.
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Sitter Profile Image: Bianca H.
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11. 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: Sarah R.
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Sitter Profile Image: Sarah R.
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12. 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!

Sitter Profile Image: Dana G.
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Sitter Profile Image: Dana G.
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13. 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: Kristin B.
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Sitter Profile Image: Kristin B.
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14. 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.

Sitter Profile Image: Cheyanne R.
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Sitter Profile Image: Cheyanne R.
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15. 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 really great with pets and she loves taking care of dogs especially. My dog, Chiky, loves it when Cheyanne comes around to take care of her. I have also seen Cheyanne take care of other dogs too and the way she cares for them and really loves being around them is awesome to see. She has a lot of expertise, and is very responsible while taking care of animals. I would recommend her to anybody looking for a good dog sitter.

Sitter Profile Image: Bianca G.
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Sitter Profile Image: Bianca G.
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16. 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!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Stacey U.
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Sitter Profile Image: Stacey U.
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17. 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

Stacey did a great job watching our dogs while out of town for the weekend. She sent pictures of them hanging out throughout the weekend and maintained good communication! Thank you Stacey!

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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!

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Sitter Profile Image: Dina J.
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Sitter Profile Image: Dina J.
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19. 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.

Sitter Profile Image: Sean J.
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Sitter Profile Image: Sean J.
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20. Sean J.

My name is Sean
Lexington, KY, 40517
15.8 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
8 reviews
5 repeat clients
from
$40
per night

Miles loves visiting Sean and Sean does great with our puppy. So glad to have found Sean!

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How Rover works

  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
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

Why choose Rover?

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  • Reservation protection

    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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