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Drop-In Visits in Winchester

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

Tip: Contact sitters now to confirm availability.
1. Sidney

Experienced but affordable sitter

Mt Sterling, KY, 40353

House Sitting, Drop-In Visits

"Sidney has had dogs nearly her entire life. She has always been a caring person towards people and animals alike. She has taken care of my 2 dogs and 2 cats ... (more)"

Confirmed 4th of July Availability
2. Candice

Dogs call me Aunt Candi

Eastland Park-Dixie Plantation, Lexington, KY, 40505

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

"Excellent! Great communication and flexible schedule ... thanks! (more)"

3. Heather

Lots of room to play on 10 acres!

Lexington, KY, 40515

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

"Heather was great with Fisher. We were new to Rover.com and the speed of communication was outstanding. The updates each time she came to visit put me at e... (more)"

Confirmed 4th of July Availability
4. Lynda

Doggy lover!

Mount Sterling, KY, 40353

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

"Lynda did such a wonderful job with our fur babies! She loved them like her own. She sent several updates and even pics! We knew they were in fantastic hands... (more)"

5. Keisha

UK Animal Science Student

Idle Hour, Lexington, KY, 40509

House Sitting, Drop-In Visits, Dog Walking

"Absolutely wonderful!! Keisha came and met my 2 cats before I left and they took to her well. She sent me a picture and update when she came by. I will abso... (more)"

6. 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)

Confirmed 4th of July Availability
7. Katie

Where Critters are KIDS!

Bryan Station, Lexington, KY, 40505

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

"Hello, First, I have known Katie Gerber all of her life. She's smart, driven, caring and kind. She's has always had pets and they were ALWAYS the cen... (more)"

8. Elisha

Home full time- love walking pups!

Winchester, KY, 40391

Drop-In Visits, Dog Walking

About: Hello! I'm currently home full time and love to walk pups. My best friend in the whole world is my Scotty mix pup Willie. We love to hang out all d... (more)

9. 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)"

10. Marlize

Best puppy vacation destination!

Lexington, KY, 40509

Dog Boarding, Drop-In Visits, Dog Walking

"Marlize has a heart for animals! She is patient and loving with every animal I've seen her with. She treats every pet as if they were her own and she's one o... (more)"

11. Kendahl

Responsible and fun! :)

Lexington, KY, 40509

Drop-In Visits, Dog Walking

About: I am 22 years old and have owned several dogs all my life. Raised on a farm, they really are a vital part of my life! I currently have five: a Gre... (more)

12. Maryann

Trusted sitter, donates 3% to KHS!

Lexington, KY, 40515

Drop-In Visits, Dog Walking

"Maryann was a perfect fit and went above and beyond the call of duty. Our chihuahua's separation anxiety is pretty severe, but Maryann made sure that her vis... (more)"

13. Zach

Mostly at school and home

Lexington, KY, 40509

Drop-In Visits, Doggy Day Care, Dog Walking

About: I've always been passionate about dogs and I love every dog that I meet. I am very amicable and willing to treat your dog with the same love that y... (more)

Confirmed 4th of July Availability
14. Kylen

Your pups will never want to leave!

Lexington, KY, 40509

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

"I have known Kylen her entire life, as I am friends with her parents. There have always been dogs (usually more than one) in her household. Kylen shows com... (more)"

15. Natalie

Quality care at home!

Lexington, KY, 40509

Dog Boarding, Drop-In Visits, Dog Walking

"Natalie is amazing with dogs. I have know her and used her for years to watch my dogs. I met her at a camp where she helped get dogs, puppies and kittens ado... (more)"

16. Dima

Love hanging out with the dogs! ?

40509, KY, 40509

House Sitting, Drop-In Visits, Dog Walking

About: I Grew up on a farm in Nicholasville and dogs were always part of the family. We have had small dogs, (chihuahua, Pomeranian) medium dogs, (lab) an... (more)

17. Monika

I will run/walk/play with your dog

Lexington, KY, 40509

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

About: I am a softy for dogs! I love to play, cuddle, and run with your dog. If they're more on the chill relaxing side I am also ok with putting on a mov... (more)

18. Marquie

Home full-time, large fenced yard

Winchester, KY, 40391

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

About: Hello! I am a preschool teacher with summers off! I am a dog lover trying to make a summer living off loving your animals! I am home full time with... (more)

19. Janessa

I’ll run with your dog!

Eastland Park-Dixie Plantation, Lexington, KY, 40505

House Sitting, Drop-In Visits, Dog Walking

About: My name is Janessa and I’ve been caring for dogs and cats since I was a kid, I’m a huge animal lover and have always had a fur baby of my own. My d... (more)

20. Grant

Will give endless belly rubs

Lexington, KY, 40509

Drop-In Visits

"Grant is always wonderful with dogs. He helped care for our service dog in training and the two bonded very well. I've never seen a dog that didn't immediate... (more)"

Never beg a friend to drop in on your pets while you're on vacation again. With Rover, you can find the perfect pet sitter in seconds. Rover sitters are pet lovers, who will be happy to sit dogs, cats, caged pets, and even horses while they take care of your home. By removing common pet care obstacles, Rover ensures pets nationwide are happy and well-cared for even when their human is away, and empowers pet lovers to live happy and fulfilling lives. Founded on the belief that everyone should have the opportunity to experience the unconditional love of a pet, Rover makes it easy for you to reach trusted pet sitters who can provide the care your pet needs, when they need it.

All stays booked on Rover receive our Rover guarantee, 24/7 support, and our reservation protection.

How it works

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1) Browse Sitters

We make it easy to find affordable & reliable sitters near you.

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2) Contact Sitters

Chat about your dog and your specific needs. Even meet in person before booking if you really want to.

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3) Book & pay

Our platform makes it easy and secure. No cash necessary.

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4) Enjoy your trip

Drop off your dog without feeling guilty. Relax with regular photo updates from your sitter.