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. Lauren

Loving Sitter & Walker

Richmond, KY, 40475

Drop-In Visits, Dog Walking

1 repeat client

"Lauren has been our cat sitter for several years. She is reliable, conscientious, and caring. She really seems to love animals. Besides feeding our cats a... (more)"

3. Anna

I love taking my pups to the park!

Richmond, KY, 40475

Dog Boarding, Drop-In Visits, Dog Walking

1 repeat client

"Anna was absolutely fantastic with our pups! We reached out last minute and she was beyond accommodating (even made time for a meet and greet). Kept us updat... (more)"

4. Emree

I’ll treat your animal like my own

Richmond, KY, 40475

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

"Not only is Emree the best person you'll meet, but she's the BEST person to sit your pups! She has watched my Hank multiple times, and every time he sees her... (more)"

5. Nikitta

Animal Lover of all sizes!

Richmond, KY, 40475

House Sitting, Drop-In Visits, Dog Walking

"I have known Nikitta for a long time now, and she is one of the FEW people I would let care for my two girls while I was away. She has always treated them li... (more)"

6. 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)

7. Natalie

"Best pooper scooper in town!"

Rogers, KY, 41360

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"You know how Mowgli from the Jungle Book was one of the wolves and they all loved him? This is like Natalie and dogs. Natalie is like Daenerys from Game of ... (more)"

8. Mallorie

I’ll treat yours like mine!

Lexington, KY, 40511

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"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)"

9. 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)"

10. 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)"

11. 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)

12. Jordan

Professional Belly Rubber

Richmond, KY, 40511

House Sitting, Drop-In Visits, Dog Walking

About: I would consider myself to be fun-loving, energetic, and playful. I've grown up with a variety of different dog breeds and experienced even more wi... (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. 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)"

15. Leah

Offering Peace of Mind for Climbers

Clay City, KY, 40312

Drop-In Visits, Doggy Day Care

"I can not recommend Leah highly enough. It was like have a member of the family staying with my dog. She was amazing and we will definitely have her sit our ... (more)"

16. 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)"

17. 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)

18. Alexander

I treat your babies like my babies!

Blueberry Hill-Brigadoon-Stoneybrook-Baralto, Lexington, KY, 40517

House Sitting, Drop-In Visits, Dog Walking

"Alexander has always been a great help to me when I have to leave town for business last minute and can't find a dog sitter. He always comes and helps when h... (more)"

19. 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)

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.