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.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
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1. Meaghan

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

Richmond, KY, 40475

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

1 repeat client

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

2. Leah

Offering Peace of Mind

Clay City, KY, 40312

Dog Boarding, House Sitting, 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)"

3. Brianna

I am attentive and thorough!

Richmond , KY, 40475

House Sitting, Drop-In Visits, Dog Walking

About: All my life I have grown up around dogs. I have been house sitting for the past few years and have completely loved the experience. I take care of ... (more)

Confirmed New Years Availability
4. Monica

I will make sure your pup is HAPPY!

Richmond, KY, 40475

House Sitting, Drop-In Visits, Dog Walking

About: If I am chosen to provide care to your dog I will always do my absolute best to ensure that the highest level of care is being given. I will make s... (more)

5. Kelli

Dog Lover. Very caring and loving!

Berea, KY, 40403

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

About: I have a 4 year old pup. I treat him like a baby. I watch him like a hawk and make sure he is always happy. I plan to treat any other dog that I wa... (more)

6. Avvyella

Your Dog's Next Adventure

Berea, KY, 40404

Drop-In Visits, Dog Walking

"Avvy has a passionate love for and connection to dogs of all kinds. She gets so excited every time she meets a new four-legged friend. She knows just how to ... (more)"

7. Laura

Dog Lover & Pre-Veterinary Student

Lexington, KY, 40517

House Sitting, Drop-In Visits, Dog Walking

About: I've never lived in a home without a dog. My dogs are my best friends, and I frequently drive home from school just to hang out with them. I'd love... (more)

8. Haylie

Passionate Pre-Vet Student

Richmond, KY, 40475

House Sitting, Drop-In Visits, Dog Walking

About: I come from a family that has always had a few dogs running around, along with several other pets, and since i was young i have had to help care fo... (more)

9. 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)

10. Nicole

Life is better with paws

Richmond, KY, 40475

House Sitting, Drop-In Visits, Dog Walking

About: I love dogs and tend to find a dog everywhere I go, sometimes I prefer them over people (LOL). I have raised and provided for my 3 year old German ... (more)

11. Victoria

Experienced pet sitter

Richmond, KY, 40475

House Sitting, Drop-In Visits, Dog Walking

About: I'm a 19 year old full-time student at Eastern Kentucky University and an animal lover (aka the girl that has to pet every dog she sees). I have ow... (more)

12. Arielynn

Your Pet's Happiness is My #1 Goal!

Richmond, KY, 40475

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

"Arielynn tended to my 3 pekingese furbabies while I was out on business for a week. She's the only sitter I've had that followed my directions exactly and sh... (more)"

Experience exceptional service and a personalized match

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Learn About Premier

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.