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. Kristin

Eager to help your family

Belmont, MA, 02478

Drop-In Visits, Dog Walking

8 repeat clients

"Kristin did such a great job caring for Jackson! I know this, partly because she kept in touch very often, but also because, though Jackson was thrilled to s... (more)"

2. Susan

We love dogs like a family member

Burlington, MA, 01803

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

3 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)"

3. Kate

Graduate Student, Loves Animals!

Somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Kate has dog-/cat-sat for us on multiple occasions. She is responsible, loves our animals (and they love her!), and was even able to stay an extra night afte... (more)"

4. Catherine

Active dog lover

Somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"Catherine did a great job watching my two cats. They liked her a lot (she sent me a photo of them both cuddled up on her lap—so cute!) and were happy and pla... (more)"

5. Cameron

A life without dogs is not a life

Arlington, MA, 02476

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

1 repeat client

"Cam is a total dog lover and has 3 wonderful dogs. He is very responsible and trustworthy, and takes great care of his dogs and also his rabbit. (more)"

6. Gretchen

Woof, Woof, Woof!

North Cambridge, Cambridge, MA, 02140

House Sitting, Drop-In Visits, Dog Walking

6 repeat clients

About: Hey there! I come to Cambridge, MA with many years of professional pet-care experience (although, I've been taking care of dogs and cats for as lon... (more)

7. Manuela

Animal loving, patient and caring

belmont, MA, 02478

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Manuela was a natural with our dog Max. He seemed relaxed and well-cared for when we returned. I plan to call on her again. (more)"

8. Bryna

Kind, Caring, Loves Walks

Malden, MA, 02148

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

4 repeat clients

"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)"

9. Sophie

I spoil your dog like my own!

Reading , MA, 01867

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

46 repeat clients

"Sophie is a fantastic sitter. Our cat Lena is very frightened of new people and Sophie was able to quickly make friends with her. She kept us informed, and e... (more)"

10. Grace

Fun, friendly, happy animal lover!

Melrose, MA, 02176

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"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)"

11. 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)"

Available this weekend
12. Tracy

Active and Loving Pet Sitter!

arlington, MA, 02474

House Sitting, Drop-In Visits, Dog Walking

"Tracy is a spunky dog lover who is always on time. My dog can't get enough of her. She is both both calming and fun. Our dog is a true member of the family ... (more)"

13. Nicholas

Dog lover to the core.

Malden, MA, 02148

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

3 repeat clients

"Nicholas was great. He sent pictures of their time together and gave regular updates. No need to worry with Nicholas taking care of your pet! (more)"

14. Sara

Playful, Nurturing, Pet Lover

somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: I work freelance from home which means I can spend majority of the day with your little friends while you are away on trips or at work. I need to ... (more)

15. Beth

Full-Time Dog Lover!

Arlington, MA, 02476

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

15 repeat clients

"Beth is wonderful. She's responsive and thoughtful and dependable and reality cares for our animals (more)"

16. Mira

Doggydate:Eat, play, sleep, repeat!

Somerville, MA, 02144

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

"Mira is a wonderful dog caregiver! She dog sits and walks my puppy Max and she always takes great care of him and he literally jumps for joy when she comes o... (more)"

17. Becca

Sweet. Professional. Attentive.

Medford, MA, 02153

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Becca was awesome to work with. She was great about scheduling and always included photos and a handwritten note for each visit. We definitely hope she's ava... (more)"

18. 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)"

19. Shannon

Nursing Student/Dog Lover :)

Medford, MA, 02155

Drop-In Visits, Dog Walking

"Shannon is a dog lover. She's watched and cared for my dogs several times and always does a great job. I have 2 chihuahuas that take a while to warm up to pe... (more)"

20. Jennifer

Dog Walking Done Right

malden, MA, 02148

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

1 repeat client

"Our dogs love you! Thanks for treating them like your own! (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.