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.

Confirmed 4th of July Availability
1. Julianne

Four legged friends are my favorite

Medford, MA, 02155

Drop-In Visits, Dog Walking

"Julianne was AMAZING! I had to reach out to her very last minute. She was able to move her schedule around and help us out! She was amazing with our little ... (more)"

2. Carolyn

Caring and Responsible Dog Lover!

Medford, MA, 02155

House Sitting, Drop-In Visits, Dog Walking

"Carolyn was great! She did two drop ins for us while we were out and even a few extra things we had forgot to mention. She sent pictures and was very respons... (more)"

3. Monica

Loving and responsible dog sitter

Somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

"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)"

4. Emily

Responsible & Caring Sitter/Walker

Somerville, MA, 02145

Dog Boarding, Drop-In Visits, Dog Walking

"I can always count on Emily to take great care of my Boston Terrier Jimmy. She sends me updates on how Jimmy is doing and even shares pictures of their walks... (more)"

5. Zac

Muttsachussets is for dog lovers

Somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

"Zac is an excellent dog sitter! My Pomeranian is in love with him and always so excited to see him. He is attentive, takes her out to play ball (her favorite... (more)"

Confirmed 4th of July Availability
6. Kristen

I'll take your dog out for a sniff!

somerville, MA, 02143

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

"She’s an absolute blessing with our 2 dogs. I think they can’t wait to be with her as much as I am to see them off. She’s extremely pleasant and really knows... (more)"

7. Susan

We love dogs like a family member

Burlington, MA, 01803

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

"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)"

8. Aphia

Dogs will be cared for like family!

Arlington, MA, 02474

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

"Aphia has been a fantastic caretaker for my pup on several occasions, for both short and extended overnight stays. She's playful and an animal lover, while r... (more)"

Confirmed 4th of July Availability
9. Grace

Fun, friendly, happy animal lover!

Melrose, MA, 02176

House Sitting, Drop-In Visits, Dog Walking

"Grace was amazing with our cat while we were away! She was very quick to respond to messages and kept us updated with pictures. Grace carefully took notes an... (more)"

10. Erin

I can be your dogs best friend.

Winchester, MA, 01890

House Sitting, Drop-In Visits, Dog Walking

"Very nice person. Dogs seemed to enjoy her. (more)"

11. Samantha

Pawsitively obsessed with dogs!

Somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

"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)"

12. Annie-Eliza

Full-time professional dog lover

Somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

"Annie has a special way with animals. My dogs just love being around her positive and happy energy. One of my dogs takes a but to be comfortable around new ... (more)"

13. Peter

I will keep your dog Happy!

Medford, MA, 02155

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

About: I Have had dogs all while growing up and into my adulthood. Love all shape and sized dogs. I am available primarily after 5 pm during the week for... (more)

14. Helen

Fur Friends are Best Friends

Arlington, MA, 02474

House Sitting, Drop-In Visits, Dog Walking

"Love, love, love Helen!!!! She is the PERFECT dog sitter. I always know that my pups are in good hands when she watches them. (more)"

15. Rose

Belly Rub Guarenteed

Arlington, MA, 02474

House Sitting, Drop-In Visits, Dog Walking

"Rose took excellent care of my elderly dog with various health issues - highly recommend! (more)"

16. 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)

Confirmed 4th of July Availability
17. Genta

Home full time - A Fuzzy Vacation

Stoneham, MA, 02180

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

"Genta watched our Labradoodle for us while we were away, and the experience was amazing. Genta was great with our dog, and made sure all of his needs were ta... (more)"

18. April

Capitol Hill Dog Services!

Winchester, MA, 01890

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

"I've known April for a very long time and she has a history of caring for foster dogs. This entails turning their mindsets around and making sure they feel l... (more)"

19. Lindsay

Will work for wags

Winchester, MA, 01890

House Sitting, Drop-In Visits, Dog Walking

About: I've been pet sitting since I was a kid for my neighbors and friends. I am very active and love to walk, run and hike. I am super friendly and love... (more)

20. Danielle

Responsible Animal Lover

woburn, MA, 01801

House Sitting, Drop-In Visits, Dog Walking

"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)"

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.