Summer is here and we’re already dreaming about our next vacation or weekend getaway. Each week, we’ll pick our favorite dog-friendly Airbnb vacation rental in a city we’d love to visit—so you can pack your suitcase, grab the leash, and get out of town.

A beautifull historic house/grt rm in Winthrop

Apartment in Winthrop, United States. Beautiful rooms in a historic house and a goegeous city. Steps to the beach for a morning walk. Steps to the public transportation. Steps to the bus station. A 5 min bus ride to Orient Hight Train Station (blue line). A 5 min ride to the airport… View all listings in Winthrop

Where you’ll stay
Enjoy a private room for two in a historic house located in Winthrop, MA. The neighborhood is clean and quiet, and comprised of local fishermen and city commuters. This rental’s owner takes the stress out of traveling by welcoming both you and your dog, providing fresh towels and linens, and offering amenities like cable TV, air conditioning, and free parking with a provided permit.

Why we love it
This coastal neighborhood is less than 30 minutes from Boston proper, but retains a remote-feeling atmosphere. Breathe in the salty air with a morning walk to the park or beach with your dog, or relax in town—all are just a short walk away. If you’re yearning for some city life, Boston is just a train or car ride away.

Try some of the best pizza in Boston at Upper Crust on Tremont Street, or cool down with homemade ice cream at J. P. Licks and order your pooch the “Cow Paws”—a sorbet made just for dogs!

What you need to know
The room is available with a one night minimum stay for $75 per night. Traveling with a friend? A second room is available for $55 a night. A parking permit is provided for street parking, but a $20 deposit is required and will be returned at the end of your stay. The kitchen is at your disposal, however the owner asks there be no cooking after 8 PM, and of course, clean up after yourself. So whip up those homemade dog treats during daylight hours.

Editor’s Note: As always, we recommend that you check with the homeowner for specific restrictions on breed, size, or number of dogs allowed in the residence.


A group of dog lovers that enjoy a good game of fetch in the park, a cold drink at a sidewalk patio, and Instagramming dog selfies with the best of them. We're working hard to find the best stories about our shared dog culture for you and your best friend.