Dog Boarding in Winchester

Find a loving dog sitter to watch your dog overnight at your sitter's home.

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Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
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Confirmed availability: Easter Weekend
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
14 reviews
4 repeat clients
from
$35
per night

Madison is a natural when it comes to taking care of animals! I can just tell when i bring my dogs to her, they love going and are very excited to see her! That tells me everything i need to know!

Confirmed availability: Easter Weekend
Sitter Profile Image: Shelby B.
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Sitter Profile Image: Shelby B.
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2.

Shelby B.

Loving Care When You're Not There
Lexington, KY, 40509
12.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
104 reviews
44 repeat clients
from
$38
per night

We have had Shelby watch our dogs multiple times now. She is extremely flexible with scheduling and always sends us great updates on how our dogs are throughout their stay. She takes extremely good care of them. We will continue to use her in the future!

Sitter Profile Image: Cheyanne R.
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Sitter Profile Image: Cheyanne R.
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3.

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 have known Cheyanne for 16 years as a a close friend. As long as I have known her for, she has always had a passion for loving all animals. She grew up on a farm in which she had multiple types of pets but especially dogs. Her love for dogs has never died since she was a kid, and eventually turned into a passion for her career. Cheyanne wants to pursue becoming a veterinarian for animals like dogs. Her character also says a lot about the way she handles not just people but dogs. She always knows what to do in situations of uncertainty with big or small animals, as she has had a lifelong time of experience on the farm growing up. She has also had hands on experience working in a vet clinic in her town. She is well loved not only by the staff there but the animals as well :) These are just some examples of experience Cheyanne has gained in the realm dog caretaking, which has created her to be more than qualified to work as a Rover dog sitter!

Confirmed availability: Easter Weekend
Sitter Profile Image: Madison M.
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Sitter Profile Image: Madison M.
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4.

Madison M.

Hi there!
Lexington, KY, 40515
11.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
10 years of experience
from
$37
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 currently work full time at a thoroughbred farm in Nicholasville! When I house sit, my typical routine is to get up around 7, take care of all the fur babies and head to work! When my lunch break comes, around 12, I head back and hang out and play with all of the animals until I have to go back to work around 1. Then around 3:30/4 I head home for the night :) 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: Ashley R.
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Sitter Profile Image: Ashley R.
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5.

Ashley R.

Loving your pets like my own!
Lexington, KY, 40509
12.0 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
13 reviews
4 repeat clients
from
$40
per night

Ashley was a great sitter for our golden retriever, Thor. She was very flexible and accommodating with our changing plans. It seemed like Thor had a great time and we would love to use her again!

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Sitter Profile Image: Jeannette A.
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Sitter Profile Image: Jeannette A.
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6.

Jeannette A.

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

If there’s a better sitter anywhere I don’t know where you would find her. Jeannette loves my dog and takes care of him as if he were her own. She always stays in touch and makes sure your dog is getting the best care possible. I would never ever hesitate to recommend Jeannette. I have the upmost respect for her and her family.

Confirmed availability: Easter Weekend
Sitter Profile Image: Bianca G.
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Sitter Profile Image: Bianca G.
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7.

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
7 reviews
2 repeat clients
from
$27
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!

Sitter Profile Image: Angelica M.
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Sitter Profile Image: Angelica M.
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8.

Angelica M.

Second mommy to your fur baby!
Winchester, KY, 40391
5.7 mi. away
Boarding, Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
1 repeat client
from
$36
per night

Angelica was so nice and understanding. She took such good care of my dog and sent me lots of photos. I will definitely ask for her to watch Sage again if needed!

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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
6 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!

Confirmed availability: Easter Weekend
Sitter Profile Image: Stephanie N.
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Sitter Profile Image: Stephanie N.
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10.

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
11 reviews
1 repeat client
from
$29
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!!!

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Sitter Profile Image: Autumn H.
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Sitter Profile Image: Autumn H.
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11.

Autumn H.

Fun, loving, active family!
Marriott's Griffin Gate Golf Culb, Lexington, KY, 40511
17.8 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
14 reviews
2 repeat clients
from
$45
per night

Autumn was absolutely wonderful with my baby Koda! He really loved being with her and their family, I can tell by his big smiles in all the pictures she sent throughout the stay. I will absolutely love it if Koda continues to stay with Autumn again in the future!!

Sitter Profile Image: Micki O.
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Sitter Profile Image: Micki O.
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12.

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
14 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: Erin S.
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Sitter Profile Image: Erin S.
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13.

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 amazing with our pup! She got back to me quickly and was so accommodating with my pick up and drop off time. Duke had the best time with her dog, they played all weekend and he came home ready for a nice long nap! He was able to get lots of loving for her entire family. They took him on walks and to the park. I really couldn't be more appreciative of all the time that was spent with him. I will definitely be sending Duke back if needed again!

Confirmed availability: Easter Weekend
Sitter Profile Image: Sarah W.
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Sitter Profile Image: Sarah W.
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14.

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
42 reviews
12 repeat clients
from
$25
per night

Sarah came in clutch last minute. Full transparency I was worried about my indoor dog with her outdoor dogs/breaking routine but as far as I’m concerned, she lived the highlife inside during her stay. No issues on my end and would use again.

Confirmed availability: Easter Weekend
Sitter Profile Image: Catherine M.
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Sitter Profile Image: Catherine M.
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15.

Catherine M.

I'll love yours like my own!
Mount Vernon-Hollywood-Montclair, Lexington, KY, 40502
17.4 mi. away
Boarding, Drop-In Visits, Dog Walking
5.0 out of 5 stars
38 reviews
15 repeat clients
from
$35
per night

Catherine was great with Luna! She sent us great pictures letting us know Luna was having a great time and adjusted well to a new setting! Catherine was great with communication! Definitely would recommend for others!

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Sitter Profile Image: Tia A.
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Sitter Profile Image: Tia A.
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16.

Tia A.

I love my dogs like I love my kids
Indian Hills-Stonewall Estates-Monticello, Lexington, KY, 40503
19.8 mi. away
Boarding, Drop-In Visits, Doggy Day Care
5.0 out of 5 stars
13 reviews
5 repeat clients
from
$55
per night

Tia is amazing! She took such good care of our 1-year old lab/hound mix! He can be a little anxious in new situations, but she made him feel right at home! Our vacation was so much more relaxing because we knew he was in good hands!

Sitter Profile Image: Cheyenne C.
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Sitter Profile Image: Cheyenne C.
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17.

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.

Confirmed availability: Easter Weekend
Sitter Profile Image: Erin & Anthony C.
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Sitter Profile Image: Erin & Anthony C.
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18.

Erin & Anthony C.

Treat your fur babies like my own!
Lexington, KY, 40516
15.9 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
4 reviews
from
$40
per night

My dog, Clementine, had a great time with Erin and Anthony! I would trust them with her life. I can tell she got lots of attention/affection and was well cared for! 5 stars!

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Sitter Profile Image: Kath & Jordan R.
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Sitter Profile Image: Kath & Jordan R.
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19.

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
7 repeat clients
from
$35
per night

Kath took really good care of my German Shepard and sent frequent photo updates! Would recommend her for dog sitting. You can tell that she really cares about all dogs!

Confirmed availability: Easter Weekend
Sitter Profile Image: Kristin B.
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Sitter Profile Image: Kristin B.
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20.

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
8 reviews
1 repeat client
from
$25
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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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.

Rover also offers Dog Boarding in:

Rover also offers other services in Winchester:


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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