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. Ginie

Run & play as much as pup wants!

Winchester, MA, 01890

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"our 2 Frenchies love Euginie! (more)"

2. Stephanie

Big yard,big heart,playful doggie!

Stoneham, MA, 02180

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

7 repeat clients

"Stephanie is a very sweet, responsible person who is a pleasure to be around? She loves her family & is an animal lover? She is intelligent & accomplished in... (more)"

3. Susan

We love dogs like a family member

Burlington, MA, 01803

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

5 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)"

4. Emma

Responsible, compassionate, fun!

Belmont, MA, 02478

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"I , without hesitation, highly recommend Emma as a responsible and loving dog caregiver! My dogs are my beloved family members and have never been left in t... (more)"

5. Candice

Love to teach old dogs new tricks

Somerville, MA, 02144

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

15 repeat clients

"Candice stopped in to visit my 11 week old puppy. When I got home 2 hours later he was still tired! Candice and I met a few days beforehand for an introdu... (more)"

Available this weekend
6. Danielle

Your Pet is my PRIORITY!!!

Everett, MA, 02149

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

17 repeat clients

"Danielle was great! She responds immediately to messages and sent us a bunch of really cute pictures from each of her daily visits. We really appreciated t... (more)"

7. Susana

Trustworthy and loving pet sitter!

Medford, MA, 02155

Drop-In Visits, Dog Walking

4 repeat clients

"Susana is awesome! I was looking for someone nearby to check on my two cats and feed them and play with them while I was away for work. My cats seem to love ... (more)"

Available this weekend
8. Anna

The Asian Cesar Millan!

Melrose, MA, 02176

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

6 repeat clients

"Is your dog loud? Obnoxious? No problem! Anna is someone we call a dog whisperer. She clearly understand the way dogs work, their needs, their desires and t... (more)"

9. Stacey

productive & stress-free walks!

Lexington, MA, 02421

Drop-In Visits, Dog Walking

About: I have ten plus years experience in dog walking. I understand their basic needs and am very patience while walking with them. I care for all types ... (more)

Available this weekend
10. Nicole

Dog Lover living in a Cat World

Somerville, MA, 02145

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

23 repeat clients

"Nicole is responsible and super sweet with my elderly dog! (more)"

11. Sophia

Loving, Responsible Dog Sitter

Somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

16 repeat clients

"She did an excellent job taking care of my 2 dogs, even when one got injured while playing, she kept a close eye on her and made me feel sure she was looking... (more)"

12. Sandy

Hanging with Mosley

Malden, MA, 02148

Dog Boarding, Drop-In Visits, Dog Walking

2 repeat clients

"Excellent! Highly recommended for cat sitting. We will definitely book again. (more)"

13. Grace

Fun, friendly, happy animal lover!

Melrose, MA, 02176

House Sitting, Drop-In Visits, Dog Walking

2 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)"

Available this weekend
14. Danielle

Responsible Animal Lover

woburn, MA, 01801

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Danielle was super to deal with, communicative all along, sending photos each day she was able to visit our dog while giving us updates on his food habits an... (more)"

15. Christine

Home full time. Vet Tech experience

Somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Chris has been looking after all my pets over the course of 2 decades. She is completely trustworthy and she is a huge animal lover. Plus, she is a certified... (more)"

16. Samantha

Pawsitively obsessed with dogs!

Somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"I am the Volunteer Director at Forever Home Rescue New England where Samantha volunteers. Samantha is hardworking, reliable, and so good with the dogs! I abs... (more)"

Available this weekend
17. Kimberly

Love is a four-legged word

Medford, MA, 02155

Dog Boarding, Drop-In Visits, Dog Walking

About: I would be a great choice for a dog sitter because I have two dogs of my own. Though they do not live with me in the city (back at home with mom an... (more)

18. Katie Mae

Home full time, fenced in yard !

Winchester, MA, 01890

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

"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)"

19. Kathleen

Experienced Dog Lover/Owner

Medford, MA, 02155

House Sitting, Drop-In Visits, Dog Walking

7 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)"

20. Clara

I Like Dogs More Than People

winchester, MA, 01890

House Sitting, Drop-In Visits, Dog Walking

"Clara has been dogsitting for me for the last two years! I have a black lab mix and sheltie, and my pups absolutely adore her. She is professional, prompt, t... (more)"

Experience exceptional service and a personalized match

From start to finish, we'll handle all the details for you.

Learn About Premier

With over 140,000 pet sitters and dog walkers on Rover.com, you can easily find pet sitting near you.

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.