Pet Sitting & Drop In Visits in Winston, KY

Book a pet sitter to stop by your home a few times a day to feed and play with your cat or dog.

1. Megan

A tired pooch is a happy pooch!

Richmond, KY, 40475

Drop-In Visits, Dog Walking

4 repeat clients

"Megan was great. We had trouble with our alarm (not her fault) and she handled it like a professional. We will definitely use her again. (more)"

2. Kelli

Dog Lover. Very caring and loving!

Berea, KY, 40403

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

1 repeat client

"Kelli is great with my pups. They are always happy and relaxed when I return. Thanks so much for your help Kelli! (more)"

3. Natalie

"Best pooper scooper in town!"

Rogers, KY, 41360

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"I have know Natalie for over a decade, now, and I can affirmatively say that she is my number one go-to person for watching my dogs when I go out of town. ... (more)"

4. Maria

Vet Tech that Loves Dogs!

Winchester, KY, 40391

Drop-In Visits, Dog Walking

2 repeat clients

About: Hello! My name is Maria. I am an experienced Veterinary Technician. I have been a technician for 5+ years, as well as a dog owner all of my life. ... (more)

5. Lauren

I’ll run with your dog

Richmond, KY, 40475

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

1 repeat client
No Reviews Yet

About: I’ve been with dogs, cats, cows, and goats, my whole life. I have experience training dogs for 2 years with activities and commands such as house b... (more)

6. Kelsey

I'll be the substitute best friend!

Richmond, KY, 40475

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Kelsey was absolutely amazing with our young pup, Braxton! During the meet and greet Braxton took to her instantly. She made sure to keep us updated on her v... (more)"

7. Meaghan

It's a Pup-partay!!!!!

Richmond, KY, 40475

Dog Boarding, Drop-In Visits, Dog Walking

6 repeat clients

"Love Meaghan. She did s great job! I will definitely use her again!! (more)"

8. Kari

Flexible Schedule- Loves walks

Richmond, KY, 40475

House Sitting, Drop-In Visits, Dog Walking

"Kari is one of the most reliable caregivers you’ll be able to find to watch your dog. She grew up with dogs and is very capable of giving your dog the best p... (more)"

9. Nick

I love dogs of all shapes + sizes!

Richmond, KY, 40475

House Sitting, Drop-In Visits, Dog Walking

"Nick is a lot like Spiderman. Now hang on, before you say, "What does Spiderman have to do with walking dogs?"consider this. Just like Peter Parker, Nick lov... (more)"

10. Amanda

A dog-gone good time!

Richmond, KY, 40371

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Amanda is wonderful with all kinds of animals,especially dogs.She does a great job giving them what they need to stay healthy,including exercise.She is very ... (more)"

11. Mallorie

I’ll treat yours like mine!

Lexington, KY, 40511

House Sitting, Drop-In Visits, Dog Walking

"Mallorie is a very caring individual that has an enormous heart for animals. She treats every animal that she come into contact with like her own. As a pre-v... (more)"

12. Breanna

I'll love your dog just like you do

Reservorir, Lexington, KY, 40502

House Sitting, Drop-In Visits, Dog Walking

About: I am very flexible with my schedule, and I absolutely love all dogs! I do have a dog of my own, so I know how it is to be a pet parent and worry ab... (more)

13. Paige

Home full-time, fenced in yard

Mckee, KY, 40447

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

1 repeat client
No Reviews Yet

About: I've had pets since I was little & my parents always had me take responsibility for them, so I have experience with animals. I love dogs of any kin... (more)

14. Leah

Offering Peace of Mind for Climbers

Clay City, KY, 40312

Drop-In Visits, Doggy Day Care

"I would highly recommend Liya. She watched our dog Theo for 14 days while we went out of the country for vacation. She sent us updates via email often with p... (more)"

15. Anna

I love taking my pups to the park!

Richmond, KY, 40475

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

About: I have a female lab mix and a husky puppy who are both very playful and full of energy. We live in an apartment in Richmond and my pups love to run... (more)

16. Kierra

Let me care for your Dog!

Richmond, KY, 40475

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

About: I'm a dog lover who wants to help take care of your dogs. I will play with your dog, lay with dog, run with you dog, and have fun with your dog. I'... (more)

17. Danielle

Loving dog mom

Berea, KY, 40403

Dog Boarding, Drop-In Visits, Dog Walking

"Danielle is awesome with pups! She's super caring and responsible. I definitely trust her taking care of my own dogs and I know she will do a great job. I re... (more)"

18. Sidney

Animal lover

Berea, KY, 40403

Drop-In Visits, Doggy Day Care, Dog Walking

About: I very much enjoy being around and playing with dogs. I have had several pets throughout my life (4 Pomeranians, 1 Australian Sheppard mix, 2 Cocke... (more)

19. Lindsey

Life long love of dogs!

Nicholasville, KY, 40356

Drop-In Visits, Dog Walking

"Lindsey is like a second mother to my German Shepherd. He isn’t the easiest of dogs to watch and can often times be very stubborn but always listens to Linds... (more)"

20. Sarah

I love long walks with cute puppies

Richmond, KY, 40475

House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: I have taken care of my own two dogs and kitty since they have came into our lives many years ago. I typically dog sit/walk in Shelbyville KY and l... (more)


The next time you head out of town and need someone to take care of your pets — and check in on you home — turn to Rover. It's easy to find a loving Winston pet sitter on Rover who'll give your pet one-on-one attention while you're away, and take care of your home. Search from hundreds of trusted pet sitters in Winston, KY, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet(s). We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your house and pet sitter all through Rover — it's easy, safe, and cashless. You'll have the peace of mind knowing that your sitter has free premium insurance, a team of safety experts available 24/7, and will send you cute photo updates throughout the stay. Rover is the easiest way to find trustworthy Winston pet sitters and avoid the kennel.