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. 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)"

2. 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)"

3. Sophia

Loving, Responsible Dog Sitter

Arlington, MA, 02476

House Sitting, Drop-In Visits, Dog Walking

8 repeat clients

"Sophia was so great! We definitely plan on asking her to help out again in the future. Besides being super knowledgable and easy to communicate with, she had... (more)"

4. Kristin

Eager to help your family

Belmont, MA, 02478

Drop-In Visits, Dog Walking

3 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)"

5. Kelsey

Around the clock love & clean home

Somerville, MA, 02143

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

11 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)"

Available this weekend
6. 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)"

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. Kyla

Vegan house of animal lovers

Medford, MA, 02155

Drop-In Visits

"Kyla provides excellent care and even sent some great photos! Our cat really liked her and I was surprised that the cat even came out of hiding. Highly recom... (more)"

9. Kailey

Life is ruff! I can make it easier

Woburn, MA, 01801

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Kailey took good care of my bengal cat, Raya. She was very quick to answer text messages when I asked for updates and even sent pictures. On our last day of ... (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. 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)"

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. Sam

Mutt owner who appreciates all dogs

Arlington, MA, 02474

House Sitting, Drop-In Visits, Dog Walking

"Sam has grew up in our neighborhood, and was a great dog walker for our little West Highland terrier mix, Athena. Even at a young age, Sam was dependable and... (more)"

14. 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)"

15. Manuela

Animal loving, patient and caring

belmont, MA, 02478

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Everything went very smoothly. We were lucky to have Manuela take care of our cats! Hope to have her take care of them again sometime. (more)"

16. Brielle

An active, intelligent animal lover

Belmont, MA, 02478

House Sitting, Drop-In Visits

4 repeat clients

"Brielle did a great job with Sophie and Willie. When it came to me, Brielle was professional, responsible, courteous with all communication and I had no prob... (more)"

17. 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)"

18. Sarah

Playpal/Den Mom/Champion Cuddler

Arlington, MA, 02474

House Sitting, Drop-In Visits, Dog Walking

14 repeat clients

"Sarah was fabulous with Luke & Princess! She spent lots of time with both (beyond the agreed to time), played a lot with each and sent constant updates. We... (more)"

19. 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)

20. Robyn

Patient, Great With Puppies

Winchester, MA, 01890

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

2 repeat clients

About: Long-time dog owner and dog lover. Friendly, calm and patient. Especially good with puppies. Mature and reliable. Clean and willing to clean up.... (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.