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. Collins

Lover of woofers big and small

Medford, MA, 02155

House Sitting, Drop-In Visits, Dog Walking

10 repeat clients

"Very pleased with the services that Collins provided for our cat! She was on time and so nice to work with! We would definitely book her again! (more)"

2. Monica

Loving and responsible dog sitter

Somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Monica was great! She catsitted my 2 cats when I was away last weekend. They are both on special diets and one needs medicine, so they need visits both in ... (more)"

3. Ally

Dog Park Regular

Woburn, MA, 01801

Dog Boarding, Drop-In Visits, Dog Walking

7 repeat clients

"Ally is reliable and awesome with my cat. The first time we used her I asked her to check in on him last minute, and she did no problem. This time I needed m... (more)"

4. Susan

We love dogs like a family member

Burlington, MA, 01803

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

11 repeat clients

"Susan and Cohan were great! They came to our house to feed/play with the cats daily while we were away and the kitties loved them! Susan also sent pictures/g... (more)"

5. Alissa

Experienced dog-sitter, love walks!

Somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

"I live with Alissa and on multiple occasions I’ve brought my parents’ dog, Kia, over to house sit. Alissa always helps with Kia when I am not available. I am... (more)"

6. Ginie

Run & play as much as pup wants!

Winchester, MA, 01890

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"our 2 Frenchies love Euginie! (more)"

7. Kathleen

Experienced Dog Lover/Owner

Medford, MA, 02155

Drop-In Visits, Dog Walking

9 repeat clients

"Kathleen was great! She is obviously a dog lover, and Hank noticed that right away, as he immediately warmed up and made her his new best friend :) Her commu... (more)"

8. Dawnielle

TLC for your pup -walks, runs, play

Medford, MA, 02155

House Sitting, Drop-In Visits, Dog Walking

"You and your dog will love Dawnielle. She has cared for my pets numerous times and I would recommend her highly. Also so would my dog. She's the best! (more)"

9. Thomas

Let’s see who tires first!

MEDFORD, MA, 02155

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

1 repeat client

"Thomas is absolutely amazing with dogs! He watches mine for me when I go out of state. He s always running around with him and playing. For an older dog he a... (more)"

10. Heidi

I’ll love your dog like it’s my own

Medford, MA, 02155

Dog Boarding, Drop-In Visits, Dog Walking

"Heidi has taken care of my pup numerous times in the year that I have had her. She always comes back happy and tired! Heidi sends pictures of their adventure... (more)"

11. Ceci

I'll take good care of your puppy!

Arlington, MA, 02476

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

9 repeat clients

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

12. Joy

North Shore Getaway

Woburn, MA, 01801

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

"Our cat, Snickers, loves vacationing at Joy's apartment. Whether it's a long weekend or a several week vacation, we know Snickers is in good hands when she s... (more)"

13. Geneva

Boston's Dog Whisperer: available!

Arlington, MA, 02474

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

"If you are looking for dog care, you must hire Geneva. I am sad to let her go, but we are moving out of her area. Geneva called herself a dog whisperer w... (more)"

14. Adam

Love an active dog!

Somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Adam is a true dog lover who's face lights up at every furry friend he comes across. Being a professional belly rubber, he's also great for 2am bathroom brea... (more)"

Confirmed Memorial day Availability
15. Eric

Walk, play, socialize... Anything!

Stoneham, MA, 02180

House Sitting, Drop-In Visits, Dog Walking

"Eric did an awesome job with our two young dogs!! He was very flexible and was willing to come the very same day to give our dogs a break while we were out o... (more)"

16. Juanita

Woodland walks @end of road

Medford, MA, 02155

Dog Boarding, Drop-In Visits, Dog Walking

3 repeat clients

"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)"

17. Kat

Fitness with Fluffy!

Medford, MA, 02155

House Sitting, Drop-In Visits, Dog Walking

About: I recently moved to Boston and away from my parents and their older dachshund Maxx. I miss Maxx and would love to play with a dog again! I work fro... (more)

18. Helen

Fur Friends are Best Friends

Arlington, MA, 02474

House Sitting, Drop-In Visits, Dog Walking

8 repeat clients

"Helen is the best!!!! She has taken care of my dogs overnight a number of times and most recently did a few drop-in visits. I always return to happy, healt... (more)"

19. Heather

I’ll run with your dog!

Winchester, MA, 01890

House Sitting, Drop-In Visits, Dog Walking

About: 1+ year of kennel experience with dogs of all sizes and temperments Past experience with house sitting and pet sitting for cats Nail trimming exp... (more)

20. Samantha

Tis better to give than to retrieve

Woburn, MA, 01801

House Sitting, Drop-In Visits, Dog Walking

"Samantha has taken care of my boxer, Maya while I have been away on more than one occasion and she is always excellent! You can tell she loves working with a... (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.