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.

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

Lots of room to play on 10 acres!

Lexington, KY, 40515

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

57 repeat clients

"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 New Years Availability
2. 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)

3. Russell

Looking to spoil your dog!

University Of Kentucky, Lexington, KY, 40526

House Sitting, Drop-In Visits, Dog Walking

About: I currently work at UK and have over 15 years personal experience dog and house sitting for my direct and extended family. I am originally from Sa... (more)

4. Jamie

In our home dogs are family!

Mount Sterling, KY, 40353

Dog Boarding, Drop-In Visits, Dog Walking

About: I have had dogs my whole life! I am reliable, friendly, and would love the opportunity to share my love to other dogs! I believe that dogs are a pa... (more)

5. 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)"

6. 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)

7. 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)

8. 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)"

9. Natalie

Quality care at home!

Lexington, KY, 40509

Dog Boarding, Drop-In Visits, Dog Walking

1 repeat client

"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)"

10. Heather

Lots of room to play on 10 acres!

Lexington, KY, 40515

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

57 repeat clients

"Heather & Andrew (her husband) provided great care for our 2 boxers. They understand and appreciate large dogs and ours developed quite an attachment to the... (more)"

11. Trina

22 year old experienced sitter!

Jamestown, Lexington, KY, 40517

House Sitting

"I have used Trina for house/pet sitting for my dogs (and cats) for four years, and for pet sitting for even longer. She is devoted to the animals and has gre... (more)"

12. Russell

Looking to spoil your dog!

University Of Kentucky, Lexington, KY, 40526

House Sitting, Drop-In Visits, Dog Walking

"Russell is absolutely incredible! Lila (dog) and Princess Leia (cat) liked Russell immediately and were very well taken care of during our time away. Communi... (more)"

Confirmed New Years Availability
13. 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)

Confirmed Holiday Availability
14. Glenn

Where your Pet is our Pet!

Lexington, KY, 40509

Dog Boarding, House Sitting, Dog Walking

1 repeat client

"I have never felt like my dogs were in better hands. Glenn and Terrill took excellent care of our babies. We received multiple updates every day, and picture... (more)"

15. 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)

16. 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)"

17. 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)"

18. 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)

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Pet owners love Winchester pet sitters on Rover. 1,044 owners have reviewed sitters in Kentucky, giving them an average rating of 4.9/5.

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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.