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.

1. Candice

Love to teach old dogs new tricks

Somerville, MA, 02144

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

22 repeat clients

"Like any family, we are very protective of our furry family members. We are so fortunate to have found Candice for our last minute trip out of town. She keep... (more)"

2. Ceci

I'll take good care of your puppy!

Arlington, MA, 02476

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

7 repeat clients

"Thanks so much for taking care of tails and willow while we were gone for 3 days! (more)"

3. Collins

Lover of woofers big and small

Medford, MA, 02155

House Sitting, Drop-In Visits, Dog Walking

8 repeat clients

"Collins did a lovely job taking care of Oscar - she was very responsible and thoughtful. (more)"

4. Susan

We love dogs like a family member

Burlington, MA, 01803

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

8 repeat clients

"Thor really enjoyed his time with Susan and her kids, Cohan and Makayla. Their family really love dogs. They took really good care of Thor and was always on... (more)"

5. Ally

Dog Park Regular

Woburn, MA, 01801

Dog Boarding, Drop-In Visits, Dog Walking

4 repeat clients

"Wow! Ally replied last minute and made her way right over to take care of my guy! He is so shy and I’m totally surprised he came out of hiding to greet her. ... (more)"

6. Emily

Gingerplum Home Away Pet Services

Stoneham, MA, 02180

Drop-In Visits, Dog Walking

"Emily is a fantastic dog walker! She has been the only walker Henry has had and has always taken the best care of him. She is extremely reliable and responsi... (more)"

7. Brendan

Very experienced and responsible!

Melrose, MA, 02176

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

2 repeat clients

"I don't even know where to start! The amount of love, care and attention Brendan gave to my puppy is unparalleled. Brendan went out of his way to accommodate... (more)"

8. Ginie

Run & play as much as pup wants!

Winchester, MA, 01890

House Sitting, Drop-In Visits, Dog Walking

6 repeat clients

"our 2 Frenchies love Euginie! (more)"

9. Sereena

Guaranteed to love your dog

Medford, MA, 02155

House Sitting, Drop-In Visits, Dog Walking

"I have been best friends with Sereena since we were kids, so I can attest to her forever long love of dogs. But my most memorable moment with her and my dog,... (more)"

10. Genevieve

Experienced, dog-loving PhD student

Medford, MA, 02155

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: I grew up surrounded by pets, including a rescue pony, a chinchilla, and three adorable labradors. When I was in fifth grade, I poured over trainin... (more)

11. Alexandra

Huge park outside my front door

Winchester, MA, 01890

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

2 repeat clients

"Alexandra is a nurturing and responsible animal lover. She understands that each animal needs a different level of devotion and care. I completely trust her ... (more)"

12. Kerri

Happy Dogs & Cats Make My Day!!!

Malden, MA, 02148

Drop-In Visits, Dog Walking

"Kerri was a life saver and did everything required for my cats perfectly. Highly recommended. (more)"

13. Victoria

Loves dogs of all kinds

Arlington, MA, 02474

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Victoria loves pets of all kinds. She has cared for our dogs for a number of years and is always loving, dependable, and trustworthy. I wouldn't hesitate t... (more)"

14. Grace

Fun, friendly, happy animal lover!

Melrose, MA, 02176

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Grace was awesome! My boyfriend and I had her drop in on our two cats over Christmas week and she was great about sending photos and updates, and responding ... (more)"

15. Juanita

Woodland walks @end of road

Medford, MA, 02155

Dog Boarding, Drop-In Visits, Dog Walking

"Juanita is the most loving and caring person. She has watched my dog for almost two years on and off and I think he likes her more than me now! She feeds... (more)"

16. Maria

Wagging Tails & Peace of Mind

Stoneham, MA, 02180

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

9 repeat clients

"Maria is a fantastic dog watcher. We have had her watch our dogs since they were puppies and will happily continue to do so into the future! They are so happ... (more)"

17. Gregory

Lifelong Dog Owner & Lover

Medford, MA, 02155

House Sitting, Drop-In Visits, Dog Walking

"Gregory is a great dog caretaker! He has taken amazing care of my yorkie on multiple occasions. My dog takes a liking to him, and sometimes I worry that they... (more)"

18. Alan

Providing awesome care for your dog

Arlington, MA, 02476

Drop-In Visits, Dog Walking

1 repeat client

"August 4, 2017 To Whom it May Concern: I highly recommend Alan B. as a candidate for a dog sitter. Alan has been employed by Always Best Care as a C... (more)"

19. Willa

I'll be your dog's new best friend!

Medford, MA, 02155

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

"Willa is known as being a 'mama bear' for her incredible capacity for taking care of others. This has never been more evident than when I see Willa with dogs... (more)"

20. Katie Mae

Home full time, fenced in yard !

Winchester, MA, 01890

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

3 repeat clients

"Katie treats dogs like they're people! She is punctual, caring, responsible, and considerate...AND snuggly with all pets! She's a fan of puppy play dates, wa... (more)"

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.