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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.

Tip: Contact sitters now to confirm availability.
Confirmed 4th of July Availability
1. Nikitta

Animal Lover of all sizes!

Richmond, KY, 40475

House Sitting, Drop-In Visits, Dog Walking

"I have a 8 week old puppy and Nikitta took great care of him! She kept me updated the whole week I was gone and sent tons of pictures. I wouldn’t of wanted m... (more)"

2. Alyssa

MA student, adventurous & playful

Wilmore, KY, 40390

House Sitting, Drop-In Visits, Dog Walking

"Awesome job! She came over and walked our Corgis when we both had to work and made it so easy for us. Would definitely work with her again and recommend her ... (more)"

Available this weekend
3. Emree

I’ll treat your animal like my own

Richmond, KY, 40475

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

"I have known Emree for over 3 years and from the moment I met her she has always been kind, loving, understanding and trustworthy. She has rescued and foster... (more)"

4. Anna

I love taking my pups to the park!

Richmond, KY, 40475

Dog Boarding, Drop-In Visits, Dog Walking

"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)"

5. Maria

Vet Tech that Loves Dogs!

Winchester, KY, 40391

Drop-In Visits, Dog Walking

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)

6. 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)"

7. Lezlie

Give them the love and care!

Lexington, KY, 40511

House Sitting, Drop-In Visits, Dog Walking

"Lezlie did a WONDERFUL job! My dogs seemed so HAPPY when I returned home..YAY! My home was taken care of very nicely while I was gone too! It is sooo... C... (more)"

8. Hanna

Your dogs happiness is my priority!

Lancaster, KY, 40444

House Sitting, Drop-In Visits, Dog Walking

"Great job dropping in a couple of times to check on my two dogs while we were out of town for a 10 days. Excellent communication and updates while we were aw... (more)"

9. Kelli

Dog Lover. Very caring and loving!

Berea, KY, 40403

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

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

Confirmed 4th of July Availability
10. Lauren

Your best friend is now mine too

Richmond, KY, 40475

House Sitting, Drop-In Visits, Dog Walking

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)

Confirmed 4th of July Availability
11. Alexa

Dog proof home with fenced in yard!

Nicholasville, KY, 40356

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

"There is no greater animal lover than Alexa. She’s honest, trustworthy, dependable, reliable, and simply an all around great person with a huge love for our ... (more)"

Confirmed 4th of July Availability
12. 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)

Confirmed 4th of July Availability
13. Paige

Home full-time, fenced in yard

Mckee, KY, 40447

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

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. 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)"

15. 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)

Confirmed 4th of July Availability
16. Halie

Avid Dog Lover & Caregiver

Richmond, KY, 40475

House Sitting, Drop-In Visits, Dog Walking

About: My name is Halie! Animals are my love. I am currently an Animal Studies major at EKU looking at animal behavior and husbandry. I grew up surrounded... (more)

17. Deborah

I’ll run with your dog.

Richmond, KY, 40475

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

About: Hello! My name is Debi. I have literally always had doggos I couldn’t imagine life without them. I currently have a dog named Raymond. He is a chub... (more)

Confirmed 4th of July Availability
18. 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)"

19. 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)

20. 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)"


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.