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

4 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. 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)"

3. Catherine

Active dog lover

Somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Catherine was great! We felt very comfortable leaving our cat Toffee in her care. She came over before we left to meet us and check out the apartment which w... (more)"

Available this weekend
4. Kelsey

Around the clock love & clean home

Somerville, MA, 02143

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

12 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)"

5. 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)"

6. Casey

Experienced Veterinary Technician

Malden, MA, 02148

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Casey takes care of my two small pups 2-4 times a week and I definitely would give her 5 stars! She's great with the dogs and answers back quickly to drop in... (more)"

7. Christine

dog-loving couple on quiet street

Arlington, MA, 02474

Dog Boarding, Drop-In Visits, Dog Walking

2 repeat clients

"We had several drop in visits while we were away overnight. Christine and Rob are friendly and comfortable with the dogs. Lulu needs medication. Bella is ver... (more)"

8. Samantha

BU & Columbia Grad who loves dogs!

Arlington, MA, 02474

House Sitting, Drop-In Visits, Dog Walking

5 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)"

9. Susan

We love dogs like a family member

Burlington, MA, 01803

Dog Boarding, Drop-In Visits, Dog Walking

"Susan and her family are wonderful and caring with dogs and other animals alike. Your pooch will be in good hands with this loving family (more)"

10. Bryna

Kind, Caring, Loves Walks

Malden, MA, 02148

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

1 repeat client

"Bryna is wonderfully caring and truly loves dogs, I struggle to think of anyone I'd be more comfortable with leaving in charge of my own pets. As a long tim... (more)"

11. 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)"

12. Becca

Sweet. Professional. Attentive.

Medford, MA, 02153

House Sitting, Drop-In Visits, Dog Walking

"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)"

13. 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)"

14. Kyla

Vegan house of animal lovers

Medford, MA, 02155

Drop-In Visits

"Kyla took good care of my guinea pig! Very reliable and punctual. I'm sure she will take good care of any pet, small or large! (more)"

15. Beth

Full-Time Dog Lover!

Arlington, MA, 02476

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

5 repeat clients

"Beth is smart conscientious, reliable, and loves animals. She's taken care of our pets (dog and cat) many times and they've loved her! We highly recommend he... (more)"

16. 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)"

17. 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)

18. Sarah

Playpal/Den Mom/Champion Cuddler

Arlington, MA, 02474

House Sitting, Drop-In Visits, Dog Walking

14 repeat clients

"Sarah took great care of our temperamental pup while we were away for the 4th of July. She went above and beyond in meeting with us a few times beforehand to... (more)"

19. 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)"

20. Nina

Responsible student loves dogs!

Medford, MA, 02115

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

1 repeat client

"Nina is a very responsible dog owner and caregiver. She has tons of love and care that she gives her dog at home and I'm sure that she'll bring that passion ... (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.