Drop-In Visits in Winthrop

Book a pet sitter to stop by your home a few times a day to feed and play with your dog.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
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1. Sara

Office visits and parks galore!

East Boston, Boston, MA, 02128

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

2 repeat clients

"Sara was incredible! She took lots of photos and videos and, above all, was kind and patient with our rescue pup. We couldn't be more thankful to have found ... (more)"

2. Anna

Homeward Bound still makes me cry

South Boston, Boston , MA, 02127

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Anna made me and my girls (the dogs) feel comfortable right away. She stayed in touch with me throughout the weekend, sent pictures and I didn't have to worr... (more)"

Confirmed New Years Availability
3. Lisa

Simply, I LOVE dogs! (and cats)

Saugus, MA, 01906

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

2 repeat clients

"Lisa was awesome! She made me feel confident that my two cats were well taken care of while I was gone. Lisa sent me text updates and photos as promised to l... (more)"

Confirmed Holiday Availability
4. Danielle

Experienced Sitter!

Winthrop, MA, 02152

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

13 repeat clients

"Was great with my cat. (more)"

5. Meghan

Fun, active playmate for your dog!

South Boston, Boston, MA, 02127

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

About: I've always loved dogs and have had a family dog since I was little! Whenever my sister-in-law or friends with pups go away, I'm the first to jump ... (more)

6. Alessandra & Jennifer

Laid back, easy going, and flexible

Everett , MA, 02149

Dog Boarding, Drop-In Visits, Dog Walking

12 repeat clients

"I needed someone to take Thurgood out for me on short notice today and was a little nervous I wouldn't be able to find anyone. Luckily I did. Thurgood was a... (more)"

7. Ivy

Rated 4-paws

Winthrop, MA, 02152

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

2 repeat clients

"Ivy took great care of our pup. We will absolutely be using her again! (more)"

Confirmed Holiday Availability
8. Amanda

Focused on customer experience!

Back Bay-Beacon Hill, Boston, MA, 02108

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

17 repeat clients

"Amanda replied to our last minute request to walk the dogs and was great with them. Took them out twice and sent pictures and texts to let us know how they w... (more)"

9. Shay

Reliable Sitter-Boston Commons area

Central, Boston, MA, 02116

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

About: Your pets do miss you every time you walk out the door. They might not understand why you left them, but they can appreciate a loving & dependable ... (more)

10. Beth

I'm YOUR dog lady! Dogs are PAWFECT

Central, Boston, MA, 02113

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: I have a great deal of experience with all types of dogs. I grew up with dogs always running around the house and I wish I could have one now. I ... (more)

11. Christine

South Boston Dog Lover !

South Boston, Boston, MA, 02127

House Sitting, Drop-In Visits, Dog Walking

"Christine Kenney is a kind and caring person who loves dogs. I have a little six year old maltese that she absolutely adores and Chloe, my dog absolutely ad... (more)"

Confirmed Holiday Availability
12. Tu

WAGGING TAILS = EPIC TALES!!

South Boston, Boston, MA, 02127

Dog Boarding, House Sitting, Drop-In Visits

27 repeat clients

"I went to Cape Cod to visit a friend for a whole week and I left my beautiful shiba inu, Zoey, and corgi, Bush, with Tu for the duration of my trip. When I g... (more)"

13. Erika

A head full of dreams. All is love!

Chelsea, MA, 02150

House Sitting, Drop-In Visits, Dog Walking

"Chery is an amazing dog sitter!! She loves animals and she takes great care of the dogs entrusted to her!!! I would definitely recommend her for dog sitting. (more)"

14. Jennifer

Time to Walk, Fetch, and Run! ?

Central, Boston, MA, 02113

Drop-In Visits, Dog Walking

1 repeat client

"Jen (more)"

15. Molly

Loving, young, professional

Central, Boston, MA, 02113

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

About: Hi there, my name is Molly and I am new to the Boston area. I love dogs and I have over 5 years of experience working at a dog kennel. At the kenne... (more)

16. Olivia

a love for all dogs!

East Boston, East Boston, MA, 02128

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

5 repeat clients

About: Not only do I promise to care for your dog with energy, patience, and kindness, but also with love. I have a love for all dogs and will use this to... (more)

Confirmed New Years Availability
17. Ryan

Your dog's best friend

Chelsea, MA, 02150

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

3 repeat clients

"Ryan Kreps is an extraordinary individual. He is extremely reliable and responsible. He is always on time and wont leave until the task is sufficiently com... (more)"

Confirmed Holiday Availability
18. Ericka

Does your dog like the beach?

Winthrop, MA, 02152

Dog Boarding, Drop-In Visits, Dog Walking

"I met Ericka about 3 years ago when I began walking her beautiful rescue dog, Crystal, on a daily basis. [See: HBO Documentary "One Nation Under Dog" which... (more)"

19. Jessica

Active and Caring

Winthrop, MA, 02152

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

About: I have my own, very active, 3 year old Beagle. I pride myself on being timely and organized. I will make every effort to make your dog feel as thou... (more)

20. Shannon

Dog loving student! Reliable!

Revere , MA, 02151

House Sitting, Drop-In Visits, Dog Walking

About: I've had dogs my whole life and I love spending time with them. I've helped family friends with dog sitting and dog walking while they go on vacati... (more)

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Pet owners love Winthrop pet sitters on Rover. 42 owners have reviewed sitters in Winthrop, MA, giving them an average rating of 4.9/5.

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Rover.com is the simple, savvy way to find and book drop in pet sitting. It's easy to find the perfect pet sitter - many sitters have worked through Rover for years pet sitting, and 95% of reviewed stays have received a perfect five-star rating. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Pet sitters on Rover have the option to complete a free background check, which you can see from their background check badge. Pet sitters are booked on Rover every minute of every day, and 92% of the population lives within a short drive of one of the more 40,000 sitters who've listed their services on Rover, so you're sure to find the perfect pet sitter on Rover. When you book with one of our trusted pet sitters on Rover you get peace of mind that your home and pets are in loving hands.