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. Beth

Full-Time Dog Lover!

Arlington, MA, 02476

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

9 repeat clients

"When I got my puppy I was struggling to find someone reliable to let him out while I was at work all day. After I hired Beth I didn't have to worry about tha... (more)"

2. Gretchen

Woof, Woof, Woof!

North Cambridge, Cambridge, MA, 02140

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Overall great experience! (more)"

3. Sung Jae

Central Square couple next to park

Cambridgeport, Cambridge, MA, 02139

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

2 repeat clients

About: My wife and I adopted Tommy, a mini-pinscher / chihuahua mix , a few months ago (Male, just over 1 years old), and are very much enjoying our time.... (more)

4. Claire

If I weren't a person, I'd be a dog

Riverside, Cambridge, MA, 02139

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: I've been dog walking, dog sitting, and dog hanging for many years, and I absolutely love animals of all kinds. I grew up with dogs and can't get ... (more)

Confirmed Easter Weekend Availability
5. Sophie

I spoil your dog like my own!

Reading , MA, 01867

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

41 repeat clients

"Sophie's a lovely young lady, and she sent some nice photos and videos of our cat Moose when she visited him for one-hour visits while we were away. It made ... (more)"

6. 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)"

7. Steve

PAWSitively Pumped 2 Pamper UR Dog!

Somerville, MA, 02145

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

2 repeat clients

"Steve did a great job! He sent me lots of photos and the dogs looked very happy in the photos he sent. Will definitely be using him as a dog walker again. Th... (more)"

8. Christa

I am a compassionate, dog lover!

Lexington, MA, 02421

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: I am a huge advocate for all of Gods creatures however I have a special love and sensitivity to canines. I have had dogs all my life and know how ... (more)

9. 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)"

10. Sarah

Playpal/Den Mom/Champion Cuddler

Arlington, MA, 02474

House Sitting, Drop-In Visits, Dog Walking

15 repeat clients

"Sarah is our preferred dog sitter. We love her constant communication while we are away, her love of our pugs, and her flexibility when our crazy schedule c... (more)"

11. Molly

I love all types of dogs!

medford, MA, 02155

House Sitting, Drop-In Visits, Dog Walking

"Molly is an energetic young woman who loves animals, especially dogs and horses. I have watched her interact with our dogs. They like being around her becau... (more)"

12. Alex

Loving and attentive dog sitter!

Somerville, MA, 02143

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

"Alex became one of my dearest friends when we met in college a few years ago. She has always been outspoken about her love of dogs, which is why I had no fea... (more)"

13. Courtney

Experienced Pet Caregiver For Hire

Somerville, MA, 02114

House Sitting, Drop-In Visits, Dog Walking

"I can't speak highly enough of Courtney. She's great with animals, and as a bonus has experience with large dogs (she herself has a German Shepherd, Theo) as... (more)"

14. Henrik

Loving experience away from home

North Cambridge, Cambridge, MA, 02140

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

About: I grew up taking care of dogs from a highly energetic Alaskan Husky to a fetch-loving Boykin Spaniel. I am a great playmate and am flexible to do w... (more)

15. Kate

Active and reliable dog walker

Somerville, MA, 02145

Drop-In Visits, Dog Walking

1 repeat client

"Kate is super super nice. Our cats have been in very good care. Thanks for your help! (more)"

16. Ryan

I am OBSESSED with dogs!

Somerville, MA, 02144

House Sitting, Drop-In Visits, Dog Walking

"Rest assured that Ryan will look after any dog as if it were his own- he is incredibly responsible, active enough for even the most energetic of dogs, and si... (more)"

Confirmed Easter Weekend Availability
17. Alyssa

B.S. in Animal Science=Love Animals

Winchester, MA, 01890

House Sitting, Drop-In Visits, Dog Walking

"Alyssa is an extremely responsible and caring individual. She has a lot of experience taking care of animals and always goes above and beyond in her duties.... (more)"

18. Ashley

Loving dog sitter!

Stoneham, MA, 02180

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Ashley is well suited to be a loving dog caregiver. She loves her mini dachshund Willie more than life itself! She takes great care of her dog on a daily bas... (more)"

19. Tracy

Active and Loving Pet Sitter!

arlington, MA, 02474

House Sitting, Drop-In Visits, Dog Walking

"No one puts a smile on my face like my mutt Kitty, but as she enters her golden years, I'll be the first to admit she can be a handful. There are not too ma... (more)"

20. Sam

Mutt owner who appreciates all dogs

Arlington, MA, 02474

House Sitting, Drop-In Visits, Dog Walking

"I highly recommend Sam as an extremely responsible and warm, caring dog caregiver. Sam cared for my dog, Maggie, for 3 years, feeding and walking her and spe... (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.