Dog Boarding in Winston, KY

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Top rated Winston dog boarders

Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Cheyenne C.
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Cheyenne C.
from
$45
per night
5.0 out of 5 stars
48 reviews
16 repeat clients
28 years of experience
Richmond, KY, 40475

Amazing experience! I was very nervous about leaving him but Cheyenne, her family, and her dogs were amazing and Koda had so so much fun! We will definitely be sending him again!

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Jac C.
Sitter Profile Image: Lexi L.
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Lexi L.
from
$25
per night
5.0 out of 5 stars
2 reviews
8 years of experience
Richmond, KY, 40475

She was super!!! I will definitely be booking her again. I even booked her as I am an out of town person!!!

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J D.
Sitter Profile Image: Elena S.
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Elena S.
from
$50
per night
5.0 out of 5 stars
33 reviews
12 repeat clients
5 years of experience
Richmond, KY, 40475

Elena was great. She was very responsive and sent pictures of my babies at least once a day, and my babies ALWAYS looked have. Will definitely be using her services again.

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Heather G.
Sitter Profile Image: Madison A.
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Madison A.
from
$35
per night
5.0 out of 5 stars
23 reviews
7 repeat clients
10 years of experience
Winchester, KY, 40391

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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Samantha O.
Sitter Profile Image: Debra A.
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Debra A.
from
$35
per night
5.0 out of 5 stars
10 reviews
4 repeat clients
20 years of experience
Lexington, KY, 40515

I am so thankful to have found Melody. My dog, Opal, took to her right away, and she LOVES being over there for daycare and overnight stays. The times are super flexible, and I’m thankful to have someone that loves my dog as much as I do! I get pictures and videos on how Opal is doing throughout the day. Definitely the best dog sitter in Lex!

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Amie C.
Sitter Profile Image: Kathryn M.
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Kathryn M.
Star Sitter
from
$25
per night
5.0 out of 5 stars
126 reviews
40 repeat clients
5 years of experience
Nicholasville, KY, 40356

Kathryn is a great sitter! Our pup gets lots of personal attention as she will only accept one family at a time and works from home. He loves having kids around during the day and playing ball in her fenced yard. Kathryn is easy to communicate with and we feel much better about leaving our pup in her care than boarding, especially when she sends pictures and updates, which we love. She is always out top choice when when our pup cannot travel with us!

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Donna L.
Sitter Profile Image: Selena M.
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Selena M.
from
$30
per night
5.0 out of 5 stars
2 reviews
7 years of experience
Irvine, KY, 40336

Selena was absolutely wonderful! So many pictures and updates. We were so happy with all the continuous communication throughout our dogs stay with her. She is so nice and the dogs had plenty of outdoor time and play with her friendly dog! Would definitely recommend!

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Pat L.
Sitter Profile Image: Natasha T.
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Natasha T.
Star Sitter
from
$40
per night
5.0 out of 5 stars
39 reviews
8 repeat clients
20 years of experience
Jamestown, Lexington, KY, 40517

Natasha was a good communicator and sent pictures of our girl while we were away! She took our golden on walks and played with her. She also was a huge help to us by picking up and dropping off our golden when we had early/late flight times. She was a huge help and we felt great about leaving our Honey girl with Natasha!

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Taylor F.
Sitter Profile Image: Jennifer B.
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Jennifer B.
from
$38
per night
4.9 out of 5 stars
120 reviews
58 repeat clients
20 years of experience
Lexington, KY, 40515

Banjo seemed to enjoy his time with Jennifer. We appreciate the photos and update. Will definitely book with Jennifer again! Thanks so much for your care!

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Paula S.
Sitter Profile Image: Erin S.
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Erin S.
from
$35
per night
5.0 out of 5 stars
92 reviews
40 repeat clients
20 years of experience
Lexington, KY, 40515

Erin is great! She sent me updates every day and pictures of my dog. She responds promptly to all messages. She is very kind and caring person. My dog was happy and healthy when I picked her up. I would highly recommend Erin.

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Tatjana J.
Sitter Profile Image: Jason & Brooke C.
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Jason & Brooke C.
from
$30
per night
5.0 out of 5 stars
42 reviews
13 repeat clients
15 years of experience
Nicholasville, KY, 40356

Jason and Brooke welcomed Winston as one of their own. They communicated very effectively and timely. Winston had some stomach issues while we were away and they were so patient and kept us informed on his tummy stuff. We will definitely rebook again!

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Kristie L.
Sitter Profile Image: Vanessa A.
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Vanessa A.
from
$25
per night
5.0 out of 5 stars
4 reviews
1 repeat client
18 years of experience
Winchester, KY, 40391

Would Highly Recommend Vanessa! She was awesome and made sure my daisy girl was in awesome care! Sent pictures and updates all weekend!!

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Clayton P.
Sitter Profile Image: Megan D.
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Megan D.
Star Sitter
from
$45
per night
5.0 out of 5 stars
17 reviews
3 repeat clients
18 years of experience
Idle Hour, Lexington, KY, 40509

Megan takes such good care of Sophie! Sophie is on more meds now that she’s older and Megan is so good about asking any questions and keeping up with the medication chart. We were unable to fly home after the Caribbean air space was shut down and Megan kept Sophie even longer until we returned. We appreciated it so much. We will definitely book with Megan again!

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Kathy B.
Sitter Profile Image: Brandon C.
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Brandon C.
from
$30
per night
10 years of experience
Richmond, KY, 40475

About: I will go above and beyond! Baths, walks, play time, and replenishing food if needed! No dog or cat is too much! Love al furbabies Currently coaching at EKU the cheer team and looking for some extra money! This is a dream job for me! Will watch at your house! I have 4 friendly dogs and they love other animals! Willing to do what it takes to take care of your animals! I’m free anytime!

Sitter Profile Image: Neftali R.
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Neftali R.
from
$25
per night
5.0 out of 5 stars
14 reviews
3 repeat clients
7 years of experience
Idle Hour, Lexington, KY, 40509

We went out of town for a week leaving our one year old Bulldog with Nef. He came to meet our dog and even accommodated transportation. My dog is very picky on who she likes however it was love from first sight. This was the first time we had to board our dog and now we have our go to person for life. Thanks Nef for the outstanding service!

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JC
Sitter Profile Image: Dina J.
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Dina J.
from
$20
per night
5.0 out of 5 stars
260 reviews
63 repeat clients
20 years of experience
Lexington, KY, 40509

We have used Dina multiple times. She is great with the pups and I know they have a great time. They always come home exhausted. Dina also sends lots of pictures/ updates, which I really appreciate.

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Libby S.
Sitter Profile Image: Brian C.
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Brian C.
from
$45
per night
5.0 out of 5 stars
14 reviews
5 repeat clients
15 years of experience
Idle Hour, Lexington, KY, 40509

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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Kyle W.
Sitter Profile Image: Gloria D.
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Gloria D.
from
$30
per night
5.0 out of 5 stars
14 reviews
3 repeat clients
20 years of experience
Winchester, KY, 40391

Gloria was amazing with my Riley! I contacted her super last minute due to an emergency and she was very willing to accommodate our needs- she even gave him a bath! I cannot recommend her enough. We’ll be booking again with Gloria!

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Jordan M.
Sitter Profile Image: Addie B.
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Addie B.
Star Sitter
from
$40
per night
4.9 out of 5 stars
135 reviews
67 repeat clients
15 years of experience
Blueberry Hill-Brigadoon-Stoneybrook-Baralto, Lexington, KY, 40517

Addie is fantastic!! We met her twice before we left town just to be sure things were all set— and our dog loves her. We were flexible about where she stayed with our dog- her house or ours- because we were gone for 16 days. She did everything she could to make sure we were comfortable with her. She sent pictures, responded quickly to texts, and Levi’s know how everything was going. Additionally, Addie is a genuinely nice person who is driven in her work as a dancer. We were very impressed with her. We are looking forward to many more trips, knowing our dog is safe and well loved in our absence.

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Jeanne E.
Sitter Profile Image: Kristin B.
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Kristin B.
Star Sitter
from
$60
per night
5.0 out of 5 stars
46 reviews
14 repeat clients
8 years of experience
Mount sterling, KY, 40353

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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pablo m.
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Dog Boarding FAQs

Frequently asked questions about Rover

If you’re searching for a Winston dog boarding sitter for the first time, visit the sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a sitter before, learn more about how to do this in the Rover app or on your computer.

Typically, dog boarding sitters on Rover respond in under an hour, so you should be matched with the perfect sitter for you and your dog in no time!

Experience can vary widely from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when comparing sitters available in Winston.

Rover makes it easy to find Winston dog boarding sitters to provide loving care from their own home. The background-checked, 5-star sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog boarding is great for:

  • Dogs of all ages and abilities, including puppies
  • Pet parents looking for a safe, loving alternative to a kennel
  • Dogs who’d love to socialize with their sitter’s pets

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog boarding sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your dog boarding sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your dog boarding service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.