Doggy Day Care in Winchester

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Top rated Winchester doggy day care sitters

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

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Sitter Profile Image: Kayla C.
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Kayla C.
Star Sitter
from
$35
per day
5.0 out of 5 stars
157 reviews
66 repeat clients
5 years of experience
Winchester, KY, 40391

Kayla has watched my senior dog several times now. My dog has massive separation anxiety, and Kayla is great with her. Harley seems relaxed when she gets home, which is usually a good indicator that she had a good day. Kayla is also an excellent communicator.

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Bailey B.
Sitter Profile Image: Madison A.
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Madison A.
from
$25
per day
5.0 out of 5 stars
23 reviews
7 repeat clients
10 years of experience
Winchester, KY, 40391

Jasper had a great time with Madison and her dogs. She texted me a picture of Jasper while she was watching him and let me know how he was doing. It was easy to communicate with her. I would leave Jasper in her care again.

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Tara H.
Sitter Profile Image: Sonya B.
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Sonya B.
from
$50
per day
4.7 out of 5 stars
31 reviews
5 repeat clients
15 years of experience
Winchester, KY, 40391

Gunnar had the best time with Sonya and of course her Doodles. If we ever return to visit- I would use her again! Thank you so much for keeping my mind at ease so we could enjoy the parks!

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Jennifer H.
Sitter Profile Image: Natasha T.
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Natasha T.
Star Sitter
from
$30
per day
5.0 out of 5 stars
39 reviews
8 repeat clients
20 years of experience
Jamestown, Lexington, KY, 40517

Natasha was great! She was quick to communicate, open and easy to work with. She was very responsible and help put an anxious pet parent at ease!! We received updates throughout the day. Highly recommend!

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Tyler B.
Sitter Profile Image: Debra A.
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Debra A.
from
$30
per day
5.0 out of 5 stars
10 reviews
4 repeat clients
20 years of experience
Lexington, KY, 40515

Debra was wonderful! I have one dog who is very anxious and she was so patient with him to make sure he was going to be comfortable in a new environment. She has a wonderful fenced backyard which was important to me as my anxious dog doesn’t do well on walks. I will definitely be using her again.

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Anne D.
Sitter Profile Image: Casey N.
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Casey N.
Star Sitter
from
$30
per day
5.0 out of 5 stars
241 reviews
97 repeat clients
10 years of experience
Lexington, KY, 40509

Casey was the best with our pup, we traveled from out of state and was in need of a sitter while we took care of business and attented a family graduation. Casey was so caring to our pup, gave me updates along with pics everyday. I highly recommend her for doggy day care.

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Cindy M.
Sitter Profile Image: brent f.
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brent f.
Star Sitter
from
$24
per day
5.0 out of 5 stars
17 reviews
4 repeat clients
45 years of experience
Blueberry Hill-Brigadoon-Stoneybrook-Baralto, Lexington, KY, 40517

Ollie had a great time! Brent sent pics and was a great communicator! If we're back in Lexington, we will definitely have Ollie stay here again!

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

Cheyenne took wonderful care of our Jax. He had a blast playing with her dogs and made a new friend, Romero. Her kids took to him right away. As labs do, he got muddy and she went over and above by bathing him. She sent frequent pics and videos of him playing. We will definitely use her again if we are in the area again.

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Ricky Y.
Sitter Profile Image: Tanya F.
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Tanya F.
from
$30
per day
5.0 out of 5 stars
17 reviews
6 repeat clients
10 years of experience
Lexington, KY, 40509

Amazing overall sitter! Very kind and goes out of her way to make this a great experience for both me and Harley. Will continue to use her services!

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Angie M.
Sitter Profile Image: Emily D.
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Emily D.
Star Sitter
from
$35
per day
5.0 out of 5 stars
18 reviews
3 repeat clients
25 years of experience
Lexington, KY, 40511

Emily and her pups were great! She was very welcoming and flexible with her time. She has an amazing fenced in yard. I felt very comfortable with her, and she was very patient and worked with my dog to get her settled. My doggie was very anxious, and Emily was very patient! Already have another booking with her for boarding!

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Holly H.
Sitter Profile Image: Robert & Heather H.
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Robert & Heather H.
from
$27
per day
5.0 out of 5 stars
2 reviews
1 repeat client
35 years of experience
Lexington, KY, 40509

About: We've owned and cared for dogs for over 35 years. Our first dogs were a Lab and a Golden Retriever then a Pug and a Puggle and now the parents of a Lab/Husky mix. We provide loving care with plenty of exercise in our non-smoking, fenced home. We live one block from Jacobson Park and its wonderful dog parks so rest assured your fur baby will receive plenty of attention, exercise, fun and love during its stay. I work from home and my spouse is a stay at home spouse, so we are available to provide constant care, exercise, play time and supervision for your fur baby. Whether is romping in the fenced yard or walks to the dog park, your furry friend will enjoy being part of the pack with our dog. Our fenced yard and quiet cul de sac on a golf course and located a block from 2 dog parks is a great place for your dog to stretch its legs and play to its heart's desire. During warmer times, we'll also spend a lot of time relaxing with your pet in our screened in deck in the back yard with access to our fenced in yard.

Sitter Profile Image: Laura P.
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Laura P.
from
$29
per day
5.0 out of 5 stars
39 reviews
9 repeat clients
10 years of experience
Virginia Ave, Lexington, KY, 40511

Laura did a fantastic job watching my puppy Alma! She watched her for multiple days and each day Alma came home a happy pup. I got a detailed report on the day and felt very secure trusting Alma in her care.

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Anna V.
Sitter Profile Image: Kristin B.
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Kristin B.
Star Sitter
from
$40
per day
5.0 out of 5 stars
46 reviews
14 repeat clients
8 years of experience
Mount sterling, KY, 40353

Kristin and her husband were great! My dog had a blast playing with their dogs and came home happy and tired. You can tell they truly care about dogs—highly recommend.

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Mark B.
Sitter Profile Image: Casey C.
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Casey C.
from
$18
per day
5.0 out of 5 stars
4 reviews
1 repeat client
4 years of experience
Paris, KY, 40361

About: Hi, My name is Casey and I would love to be able to take care of your animals. I love all kinds of animals! I can provide any of the services listed. I am not new to taking care of animals and I have house sit for people before. I work full-time on this app. If you have any questions please feel free to message me! I have two cats and two dogs at home so I spend plenty of time with all of them by playing with them, feeding them, showing them new activities, and spoiling them! We have a fenced in back yard. I always listen to instruction's so anything your pet needs I will be happy to help with! Always looking forward to meeting new animals!

Sitter Profile Image: Amy H.
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Amy H.
from
$40
per day
5.0 out of 5 stars
18 reviews
4 repeat clients
25 years of experience
Mount Vernon-Hollywood-Montclair, Lexington, KY, 40502

Amy is great caring for your pet

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Travis M.
Sitter Profile Image: Ashtin & Jenison T.
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Ashtin & Jenison T.
Star Sitter
from
$28
per day
5.0 out of 5 stars
57 reviews
14 repeat clients
30 years of experience
Lexington, KY, 40514

Ashtin & Jenison have completely won me over as a helicopter parent. I truly feel like my dog is safe and cared for with them. They are very trustworthy and knowledgeable. I cannot recommend them highly enough!

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Finnley R.
Sitter Profile Image: Amiyah J.
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Amiyah J.
from
$32
per day
2 years of experience
Fairway-Liberty Heights, Lexington, KY, 40505

About: Ive had a total of 2 dogs and 1 cat and 2 kittens. Also I have pet sat a variety of animals from cata and dogs to even snakes. All well taken care of and loved. I know exactly how important our little friends are and I would protect them and take care them as my own. I am currently on leave from my regular job so I have all the time in the world to pet sit and it would work in well with the daily walka I take my own child on. I have a two different parks very close to my home that I tale my child and a baby gate to ensure that no one will go anuwhere unsafe.

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

About: I’ve had dogs since I was a kid. I’ve cared for friends and families dogs of all sizes and ages. I currently have a female American bully but in the past I’ve had English mastiffs, pit bulls, and a border collie. I enjoy high energy dogs that love to run and play as well as older dogs that just want to play around and be loved on. I’m currently on summer break. I am an athlete at Eastern Kentucky University and have required practices every day but I’m gone no longer than 3 hours per day. I currently live in an apartment with a dog park on site I also have one friendly and very active pup to keep yours company. I will always be outside with the pups they are never out there alone.

Sitter Profile Image: guadalupe m.
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guadalupe m.
from
$35
per day
5.0 out of 5 stars
18 reviews
9 repeat clients
5 years of experience
Thoroughbred Acres-Kingston, Lexington, KY, 40505

Guadalupe was great with our girls. So easy to communicate with, kept us updated with pics and videos and even provided a great restaurant recommendation. If we come back through Lexington, we will return to Guadalupe.

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Monica P.
Sitter Profile Image: Angela D.
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Angela D.
from
$30
per day
5.0 out of 5 stars
3 reviews
2 repeat clients
10 years of experience
Thoroughbred Acres-Kingston, Lexington, KY, 40505

About: Hello there! My name is Angie and I'm a pet sitter in Lexington, KY. When you hand over the leash, you deserve to feel completely at ease. I’m Angie — a reliable, trustworthy sitter and walker who genuinely loves dogs — and as a dog owner myself, I know exactly what pet parents need: clear communication, consistency, and someone who actually cares. I offer dog walking, drop-in visits, boarding, and house sitting, and I’m comfortable with all sizes and breeds. My home has a fully fenced yard, so boarding and visits are safe and stress-free. I keep my schedule flexible to work around yours, and you’ll always get photo and update check-ins so you can see your pup is happy and thriving. Your dog won’t just be watched — they’ll be loved. I’m retired, so I’m home all day and your pup won’t just be sitting around waiting for me. I’ve got nothing but time for belly rubs, walks, and cuddles. Your fur baby will be treated like family, because honestly, that’s just how I am!​​​​​​​​​​​​​​​​ I have a fenced in yard of over 1/2 an acre with two friendly dogs! We will have playtime outdoors and they can come and go as they please with the doggie door

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Over 17
pet parents in Winchester have booked doggy day care

Winchester dog parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Ebony was able to help us out last minute with amazing doggy daycare for a full day. She was very friendly, professional, and kind! Our dogs had a blast with her, and I would recommend Ebony to anyone needing a responsible and reliable doggy sitter!

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Pat L.
Doggy Day Care
1 / 1
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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

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  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!

The median cost per day for doggy day care in Winchester is $30

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.

  • World-class support

    We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.

Sitters in Winchester average 3
repeat doggy day care clients

Doggy Day Care FAQs

Frequently asked questions about Rover

Sitters on Rover are free to set their rates. The median cost to hire a sitter for doggy day care in Winchester on Rover as of Jun 2026 was about $30 per day, after factoring in Rover’s service fees. A sitter’s rate may also change as you customize your booking to fit your and your dog’s needs.

If you’re searching for a Winchester doggy day care 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.

As of Jun 2026, 148 sitters provided doggy day care in Winchester. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, sitters offering doggy day care joining Rover must pass a background check for you and your dog’s safety.

Rover makes it easy to reach out to multiple sitters about your booking. Typically, 85% of Winchester sitters offering doggy day care respond in under an hour.

Sitters who provide doggy day care in Winchester have an average of 16 years of experience. Sitters offering doggy day care with repeat customers have an average of 3 repeat clients. Experience can vary from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when you compare sitters in Winchester.

Winchester doggy day care sitters are happy to take care of your dog while you’re at work or unavailable for the day. Book a one-time visit, or set up a regular rhythm with your favorite Winchester sitter. Drop off your dog at the sitter’s home and rest easy knowing they’ll get frequent potty breaks, plenty of playtime, and lots of love. Doggy day care is great for:

  • Puppies and high-energy dogs
  • Dogs with special needs, including seniors
  • Pet parents who work long hours
  • Dogs with separation anxiety

There are 148 sitters offering doggy day care in Winchester on Rover, so you’re sure to find the perfect match for your dog! In Winchester, 93% of sitters offer daily exercise, 93% offer medication administration, and 93% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect doggy day care sitter near you. As a reminder, sitters joining Rover must pass a background check for you and your dog’s safety.

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your doggy day care 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 doggy day care 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 doggy day care service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.