Cat Sitting in Winchester

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Top rated Winchester cat sitters

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

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Sitter Profile Image: Debra R.
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Debra R.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
14 reviews
3 repeat clients
40 years of experience
WINCHESTER, KY, 40391

Debbie was absolutely lovely. She took great care of my pups while we were out of town. I couldn’t have asked for anyone better! We video called ahead of time to go over the routine and she checked in with me while she was checking in on the pups. Have us absolute peace of mind! 10/10

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Matthew B.
Sitter Profile Image: Casey C.
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Casey C.
from
$13
per visit
5.0 out of 5 stars
4 reviews
1 repeat client
4 years of experience
Paris, KY, 40361

Casey was great watching my two cats while I was gone for over a week! Very easy communication and she sent me so many photos which was great for my peace of mind. My cats warmed up to her so quickly and the photos she was sending me cuddling with the boys made me know my cats were well taken care of while I was away. I’d recommend Casey to anyone looking for someone to watch their pet while they are away, thanks Casey!

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Margot D.
Sitter Profile Image: Dina J.
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Dina J.
from
$10
per visit
5.0 out of 5 stars
260 reviews
63 repeat clients
20 years of experience
Lexington, KY, 40509

Dina is wonderful! The pups absolutely loved her and it was so nice to know that they were being checked on while we were gone for the day. I also got some really cute photos! I highly recommend Dina!

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Kelly S.
Sitter Profile Image: Chelsea D.
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Chelsea D.
from
$14
per visit
5.0 out of 5 stars
35 reviews
8 repeat clients
16 years of experience
Winchester, KY, 40391

Chelsea is awesome! She came and cared for my baby dog at last minute’s notice during the holiday season. She intuitively understands dogs and is patient with their quirks. Definitely will be trying to book her again in the future!

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Abby I.
Sitter Profile Image: Naomi H.
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Naomi H.
from
$18
per visit
5.0 out of 5 stars
6 reviews
1 repeat client
4 years of experience
Winchester, KY, 40391

Naomi was perfect! Very open communication and cared for my pups like they were her own! 10/10

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Matthew B.
Sitter Profile Image: Laura S.
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Laura S.
from
$25
per visit
5.0 out of 5 stars
13 reviews
6 repeat clients
10 years of experience
Winchester, KY, 40391

We cannot recommend Laura enough! She took such wonderful care of our cat, Phineas, while we were away. Laura is incredibly kind, caring, and trustworthy, and it was obvious from the start that she truly loves the animals she cares for. She kept us updated with pictures and messages throughout our trip, which gave us so much peace of mind. We came home to a happy, relaxed, well-loved cat, and that means everything to us. We will absolutely be booking with her again!

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Kara K.
Sitter Profile Image: Maria L.
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Maria L.
from
$30
per visit
4.6 out of 5 stars
7 reviews
7 repeat clients
15 years of experience
Winchester, KY, 40391

Maria did an excellent job with two very hard headed dogs! We appreciated her very much!

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Raeandrea M.
Sitter Profile Image: Sara W.
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Sara W.
from
$25
per visit
5.0 out of 5 stars
2 reviews
20 years of experience
Lexington, KY, 40515

About: Hi there! I absolutely love animals and enjoy taking care of them. I’ve been watching taking care of animals since I was a kid and I just love it I absolutely love taking care of your fur babies! Their schedule is totally accustomed to your needs and wants as their owners if you create a schedule for them, that would be wonderful and allow me to take care of your fur babies as you would yourself I do services in Lexington and Winchester, I’m currently working full-time with my hours ranging from 6 AM to 4 PM 5 days out of the week! Hours may vary depending on work Hi there! I absolutely love animals and enjoy taking care of them. I’ve been watching taking care of animals since I was a kid and I just love it! I don’t offer boardings at the moment but I would love to housesit or do drop-in visits for you!

Sitter Profile Image: Joseph M.
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Joseph M.
from
$15
per visit
4.9 out of 5 stars
113 reviews
47 repeat clients
7 years of experience
Lexington, KY, 40509

Joseph does a fantastic job with our pups when we are away. The are happy and relaxed when we get home, and communication is great . Thanks Joseph !

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Diane G.
Sitter Profile Image: Kristen S.
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Kristen S.
from
$15
per visit
5.0 out of 5 stars
8 reviews
2 repeat clients
20 years of experience
Lexington, KY, 40509

Kristen did a great job for us. We contacted her at the last moment, she came to our house without a pre-booking visit, and our dog adjusted very quickly to her without ever meeting her. Kristen was punctual and followed our instructions. Overall, a great experience with Kristen.

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William C.
Sitter Profile Image: Isabella L.
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Isabella L.
from
$20
per visit
5.0 out of 5 stars
18 reviews
6 repeat clients
5 years of experience
Winchester, KY, 40391

I could tell how much Isabella loves animals and was completely confident that she would take the very best care of my baby girl. Willow was in good hands and I will definitely book Isabella again.

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Patti W.
Sitter Profile Image: Tiger Lily J.
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Tiger Lily J.
from
$15
per visit
6 years of experience
Lexington, KY, 40509

About: I’ve grown up around pets and have experience caring for both dogs and cats, including feeding, walks, playtime, cleaning up after them, and making sure they feel safe and comfortable. I’m patient, dependable, and genuinely enjoy spending time with animals and learning their personalities. I currently have a very flexible schedule and plenty of availability throughout the week. I’ll also be starting DoorDash soon, which gives me the ability to plan my hours around pet care and stay reliable for bookings. Your pet’s safety and comfort are my top priorities. I’ll always follow care instructions closely, keep pets secure on walks and during visits, provide updates when needed, and make sure they feel calm, cared for, and comfortable in my care.

Sitter Profile Image: Justina A.
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Justina A.
from
$23
per visit
15 years of experience
Lexington, KY, 40516

About: I’m 21 years old and have grown up around animals my entire life. I have hands on experience caring for a wide range of pets, especially dogs of all sizes and breeds. I’ve had dogs my whole life from Chihuahuas and Dachshunds to Pit Bulls and Belgian Shepherds so I’m comfortable with everything from small, high energy pups to large, working breeds. I still care for my childhood Dachshund and currently have a Belgian Shepherd, which has given me strong experience with daily routines, training basics, exercise needs, and attentive care. I treat every pet as if they were my own and focus on keeping them safe, comfortable, and happy while their owners are away. Pet care is my full time job, so it’s fully built into my daily and weekly routine. This allows me to dedicate my time and attention to each pet’s individual needs, whether that’s walks, feedings, playtime, medications, or just extra companionship. Since this is what I do every day, I have a flexible schedule and plenty of availability to provide reliable, consistent care and give your pets the attention they deserve. I prioritize safety, trust, and comfort in both my home and my clients’ homes. I carefully follow all instructions, maintain clean environments, secure doors and gates, and closely monitor pets to ensure they feel safe, relaxed, and well cared for at all times.

Sitter Profile Image: Tanika L.
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Tanika L.
from
$20
per visit
5.0 out of 5 stars
15 reviews
4 repeat clients
12 years of experience
Richmond, KY, 40475

I recently moved from NY to KY and was in need of someone to help care for my four dogs. I had spoken to many people and wasn’t comfortable with anyone as I had my prior dog walker in Ny for over 10 years. I found Tanika and she and I hit it off right away: she was super accommodating to my ever changing schedule. I was nervous to have my one rescue dog meet anyone because he could be unpredictable. Tanika came armed with treats and was relaxed and so easy going with all the dogs that he took to her first!!!! Tanika had been above and beyond amazing . She helps with my dogs that have medical issues and she is always there when and if I need her. She takes care of my dogs as if they were her own and I’ve never had to worry about them when I’m away. She is an absolute god send and I highly recommend her!

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Kimberleigh M.
Sitter Profile Image: Brian C.
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Brian C.
from
$20
per visit
5.0 out of 5 stars
14 reviews
5 repeat clients
15 years of experience
Idle Hour, Lexington, KY, 40509

Brian did a great job with my cats!

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Cassidy C.
Sitter Profile Image: Lindsey L.
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Lindsey L.
from
$25
per visit
5.0 out of 5 stars
29 reviews
5 repeat clients
13 years of experience
Richmond, KY, 40475

Lindsey always sends me the best pictures of my babies which is a really nice touch that i appreciate when I'm gone! I can tell she spends time with them and is thorough in her visits! She is flexible and has been a lifesaver! I know my pets are safe, healthy, and happy with her! I was admitted to the hospital unexpectedly and with very little notice she agreed to get all their needs taken care of while I was away. Thank you!!!

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Caitlin D.
Sitter Profile Image: Ashlynn S.
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Ashlynn S.
from
$10
per visit
1 repeat client
10 years of experience
Winchester, KY, 40391

About: I am a huge animal person! I have a special interest in feline care, and currently working with a bunch of feral community cats, as well as volunteering at animal shelters with both cats and dogs. I have grown up around all kinds of animals, and currently have 2 dogs and a cat. I’m currently a college student looking for employment, so my schedule is pretty open! I’m free to hang out with your pets any time right now! I have a fenced in yard, and multiple rooms to seperate and rotate if needed. My dogs are friendly, and my cat will keep her distance, likely staying in my room.

Sitter Profile Image: Olivia C.
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Olivia C.
from
$15
per visit
5.0 out of 5 stars
22 reviews
9 repeat clients
15 years of experience
Lexington, KY, 40509

Awesome handler, accommodates any time of the day and even better with the fur baby.

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Blake S.
Sitter Profile Image: Sonya B.
Verified Background Check
Sonya B.
from
$35
per visit
4.7 out of 5 stars
31 reviews
5 repeat clients
15 years of experience
Winchester, KY, 40391

About: Thank you for taking the time to read my profile and considering me to care for your fur babies!!! My expertise comes from a lifetime of being surrounded by animals along with a sincere desire to connect and learn from each one along the way. From a very early age, I was eager to help with my family’s beagle and cats and I cared for all the neighbor’s pets. With 7 acres of fenced in lush farmland, I offer an exciting activity filled property complete with a swimming pool for the water lovers. reassurance that they are in good hands . is unlike upOver the years, I've been the loving "pawrent" of many cats, a Beagle, Goldendoodles, a German Shepard, and a Chow/Pit mix... and roommates with a wide variety of breeds, ages, sizes, and personalities. I currently am Mom to 2 middle age Goldendoodles (part time), a 2yr old German Shepard, and a Jack Russell mix puppy. I am very playful with young energetic dogs, very gentle with older ones, and very patient with special needs cases. Honestly, I love them all and will treat each as my own! I have gone through basic obedience training with my dogs and can extend some beginner skills to your pups if they are in need. My schedule is very flexible as I work from home. I have a large comfortable SUV car for transporting if necessary and I send lots of pics while you're away. Every pet is treated individually with attention to their specific needs. I am available to care for cats too. I genuinely look forward to meeting your fur babies and making new friends! I work from home so I am typically available for any schedule your pup may require. I am naturally a night owl, but ok with mornings as well. My property is completely fenced in and has a secure gate. I have a spacious home and live alone. Therefor, I have multiple empty rooms and can crate or separate your pets if needed. I can usually administer oral meds and I can give potty breaks or play time as often as you'd like.

Sitter Profile Image: Pam D.
Verified Enhanced Background Check
Pam D.
from
$20
per visit
1 repeat client
10 years of experience
Winchester, KY, 40391

About: I have been dogsitting for over 5 years. The clients I have worked for I have done overnight stays, dog walks, and day sitting for up to 8-10 hours. I do have one dog I sit for that doesn’t do walks so I adjust to what the clients needs. On overnight stays, I do clean up and bring in mail/ newspaper if the clients ask. I am a big animal lover so your dog/ cat will get lots of love. I do have a clients that likes to receive pictures during my stay. The dog will get plenty of exercise and playtime. Also I am flexible and very reliable. I can provide references of my regulars if needed and their type of dog. I enjoy providing lots of fun and love. I am flexible and reliable. I am able to meet to whatever the client might need. I am available whatever day and time. I do my best to meet the needs of the client. I haven’t cared for other animals in my home besides my own. When I go to someone’s residence, I follow what the owner normally does. I am usually left instructions to follow.

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Over 40
pet parents in Winchester have booked cat sitting

Winchester cat parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Debra was AMAZING! She was so thoughtful and really gave the best care to our babies. She gave us great peace of mind while we were away. We are so thankful to have found our new babysitter!🥰

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Sigrid M.
Drop-In Visits
5.0 out of 5 stars

We cannot recommend Laura enough! She took such wonderful care of our cat, Phineas, while we were away. Laura is incredibly kind, caring, and trustworthy, and it was obvious from the start that she truly loves the animals she cares for. She kept us updated with pictures and messages throughout our trip, which gave us so much peace of mind. We came home to a happy, relaxed, well-loved cat, and that means everything to us. We will absolutely be booking with her again!

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Kara K.
Drop-In Visits
5.0 out of 5 stars

We can always depend on Kayla to take care of our cats when we are out of town. We know they are in good hands and well taken care of.

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Angela F.
Drop-In Visits
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  1. 1. Search

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The median cost per night for cat sitting in Winchester is $20

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Sitters in Winchester average 5
repeat cat sitting clients

Cat Sitting FAQs

Frequently asked questions about Rover

Cat sitters on Rover are free to set their rates. The median cost to hire a cat sitter in Winchester on Rover as of Jun 2026 was about $20 per night, after factoring in Rover’s service fees. A cat sitter’s rate may also change as you customize your booking to fit your and your cat’s needs.

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

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

As of Jun 2026, there are 156 cat sitters in Winchester. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect cat sitter near you. As a reminder, cat sitters joining Rover must pass a background check for you and your cat’s safety.

Rover makes it easy to reach out to multiple cat sitters about your booking. Typically, 91% of Winchester cat sitters respond in under an hour.

Cat sitters in Winchester have an average of 14 years of experience. Cat sitters with repeat customers have an average of 5 repeat clients. Experience can vary from cat sitter to cat sitter, but you can view reviews, years of experience, and number of repeat clients when you compare cat sitters in Winchester.

Do you simply need someone to stop by and play, feed, and scoop? Winchester cat sitters are happy to take care of your cat while you’re at work, on vacation, or unavailable for the day, even if all you need is a quick drop-in! Your cat sitter will stop by to feed, play with, and snuggle your cat as many times a day as you like. And the best part? Your cat gets to stay on their home turf.

There are 156 cat sitters in Winchester on Rover, so you’re sure to find the perfect match for your cat! In Winchester, 94% of cat sitters offer daily exercise, 100% offer medication administration, and 100% have experience with senior cats and cats with special needs. We know each cat is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect cat sitter near you. As a reminder, cat sitters joining Rover must pass a background check for you and your cat’s safety.

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

Note: If your cat 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 cat sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your cat sitter’s cancellation policy.