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. Kristin

Eager to help your family

Belmont, MA, 02478

Drop-In Visits, Dog Walking

3 repeat clients

"Kristin was fantastic! She thoughtfully arranged a meet-and-greet with our kitten beforehand, and we were able to show her around the house. Once our cat's s... (more)"

2. Elizabeth

Adventure lover who's ready to play

Somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: After having a Great Dane/Black Lab mix named Independence growing up, I've loved taking care of and playing with dogs of all kinds! Though I don't... (more)

3. Kelsey

Around the clock love & clean home

Somerville, MA, 02143

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

11 repeat clients

"Kelsey was great to work with. She was very professional and took great care of our cat, Charlie. I also appreciated how flexible she was when our plans chan... (more)"

4. Christine

dog-loving couple on quiet street

Arlington, MA, 02474

Dog Boarding, Drop-In Visits, Dog Walking

2 repeat clients

About: My boyfriend and I adore dogs, and combined have had and taken care of dogs for about 15 years (3 Border Collies, 1 Japanese Chin, 1 Havanese, and ... (more)

5. Kyla

Vegan house of animal lovers

Medford, MA, 02155

Drop-In Visits

"Kyla is a young woman with a respect and love for animals that would make her perfect to walk dogs. She is capable and dependable, and most of all trustwor... (more)"

6. Bryna

Kind, Caring, Loves Walks

Malden, MA, 02148

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

1 repeat client

"Bryna adores dogs and they respond immediately to her passion. She's lived with and cared for dogs most of her life, and provides exceptional and skilled ca... (more)"

7. Robyn

Patient, Great With Puppies

Winchester, MA, 01890

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

2 repeat clients

About: Long-time dog owner and dog lover. Friendly, calm and patient. Especially good with puppies. Mature and reliable. Clean and willing to clean up.... (more)

Confirmed Holiday Availability
8. Catherine

Active dog lover

Somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Easy peasy! (more)"

Confirmed Holiday Availability
9. Grace

Fun, friendly, happy animal lover!

Melrose, MA, 02176

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Grace B. took very good care of my Bombay cat and she was very easy to communicate with and to work with. Highly recommended! James (more)"

10. Steve

PAWSitively Pumped 2 Pamper UR Dog!

Somerville, MA, 02145

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

2 repeat clients

"From the moment Steve arrived to meet my dogs, my mind was put at ease. He has a calm and reassuring personality and I could tell they took to him right away... (more)"

Confirmed Christmas Availability
11. Kailey

Life is ruff! I can make it easier

Woburn, MA, 01801

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Kailey was awesome! We had an emergency need for someone to take out our pup and she made it so easy. (more)"

12. Sarah

Playpal/Den Mom/Champion Cuddler

Arlington, MA, 02474

House Sitting, Drop-In Visits, Dog Walking

13 repeat clients

"Sarah was fabulous with Luke & Princess! She spent lots of time with both (beyond the agreed to time), played a lot with each and sent constant updates. We... (more)"

13. Lawrence

Energetic & Responsible

Medford, MA, 02155

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Hello Lawrence loves dogs. He helped raise our Border Collie/ Mix from a 4 month old pup until we lost him at age 15. His sister adopted a puppy shortly... (more)"

14. Samantha

BU & Columbia Grad who loves dogs!

Arlington, MA, 02474

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Samantha was great, and sent cute photos of our beloved cat while we were away! She also introduced us to the adorable word "purrito" for our very purry cat.... (more)"

15. Kathleen

Experienced Dog Lover/Owner

Medford, MA, 02155

House Sitting, Drop-In Visits, Dog Walking

6 repeat clients

"Kathleen was amazing!! She started with a meet and greet to make sure everyone was comfortable and stayed in contact the entire time she was with Jasper. I... (more)"

16. Alisa

Dog lover, friend, and admirer

Somerville , MA, 02144

Dog Boarding, Drop-In Visits, Doggy Day Care

1 repeat client

About: I have had dogs my whole life. My dad is a small animal vet so I grew up surrounded by dogs, visiting the clinic and I'm a master dog walker! Righ... (more)

17. Colin

I love dogs, walks, and playtime!!!

Medford, MA, 02155

Drop-In Visits, Dog Walking

2 repeat clients

"Colin has be an amazing resource for us and Penny. He is local to our neighborhood (Tufts / South Medford), which has allowed him to be available exactly whe... (more)"

18. Allison

Experienced dog walker

Somerville, MA, 02144

Drop-In Visits, Doggy Day Care, Dog Walking

About: I have a lot of experience with all different types of animals. I worked for a large dog walking company while living in NJ and really enjoyed wal... (more)

Confirmed Holiday Availability
19. Nancy

Vet Tech Dog Sitter, Dog Walker

Arlington, MA, 02476

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Nancy watched over my two cats over the holiday. She is highly recommended based on her communication, timeliness, flexibility, and attention to detail. She ... (more)"

20. Brielle

An active, intelligent animal lover

Belmont, MA, 02478

House Sitting, Drop-In Visits

4 repeat clients

"Brielle did a great job with Sophie and Willie. When it came to me, Brielle was professional, responsible, courteous with all communication and I had no prob... (more)"

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Pet owners love Winchester pet sitters on Rover. 28 owners have reviewed sitters in Winchester, MA, giving them an average rating of 4.9/5.

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As pet lovers, we understand how difficult it can be to leave your pet when you have to head out of town. Luckily, you can find the perfect pet sitter in seconds on Rover.com. If you're looking for trusted pet sitters while you're away, whether it's for one night or a whole month, you can find a sitter who meets your - and your pet's - needs. We manually review and approve every profile on our site, and we offer tools to help you make the right decision for your pet - including background checks, sitter testimonials, community reviews. We also offer training and extra safety tools, such as the Protection Package. And we always recommend an in-person Meet & Greet so you can see that your sitter is the perfect fit for your dog. Rover is proud to be the nation's largest network of pet lovers for hire.