The Coolest Airbnbs in Massachusetts • The Blonde Abroad

The Coolest Airbnbs in Massachusetts

Whether you are looking to take in those autumnal vibes or want to soak in the sun on the Atlantic coastline, Massachusetts is the place to be. It’s a dream destination for digital detoxes and swanky city breaks alike.

From rustic cabins to urban oases, there are so many unique accommodation options that will elevate your experience.

Here are the coolest Airbnbs in Massachusetts!

With space for nine, this sunny waterfront is a picture-perfect space for a retreat. Whether you’re traveling with kids or planning a girlfriend’s getaway, this property ticks all of the boxes.


Orange, Massachusetts

This cottage for two on the shores of Tully Pond was made for rustic retreats. Cook your dinner over the fire, grab a book from the ample library, and simply unplug.


North Adams, Massachusetts

Standing on the highest peak of the Hoosac Range, this unique space for two was is perfect for romantic escapes. Get the barbeque started, uncork that wine, and sit back to admire the breathtaking view.


Octagonal House Windows Otis Massachusetts Treehouse Berkshires Airbnb

Monterey, Massachusetts

This three-bedroom cabin, with its wood-burning fireplace and professional kitchen, has all of the modern amenities in a picturesque forest by a bubbling stream.


Rustic Berkshire Getaway Otis Massachusetts Airbnb

Otis, Massachusetts

Just outside of Jacob’s Pillow, this two-bedroom rustic space has stunning views from the spacious outdoor porch.


Modernized Historic Home North Adams Massachusetts Airbnb

North Adams, Massachusetts

Built in 1875, this two-bedroom home has been lovingly restored. With vintage touches throughout (and modern updates where it matters), this is the perfect base for exploring swanky restaurants or hiking through the waterfalls.


Rockport, Massachusetts

This quaint cabin has room for five (and your four-legged friends) in the woods of Cape Ann. Meet the neighboring miniature horses, walk to Rockport, or spend the day exploring the secluded hiking paths.


Uxbridge, Massachusetts

With room for three in the historic Uxbridge, this teeny tiny house will transport you back to the days you dreamt of having a secret fort in the backyard.


Lee, Massachusetts

This whimsical tiny house in the Berkshires looks straight out of a fairytale. If you’re looking to take your knight in shining arming away for the weekend, look no further.


Swampscott, Massachusetts

This tastefully designed penthouse has breathtaking views of the ocean. Perfect for couples, this studio space has luxe touches like a jetted tub, quartzite kitchen, and cozy space.


Rockport, Massachusetts

In Rockport, you’ll find this two-bedroom apartment with a sweeping sea view. Kayak in the harbor, sample the ultra-fresh seafood, then come back and lounge on your roof deck and take in the beautiful vista.


Marblehead, Massachusetts

This thoughtfully restored nineteenth-century home offers room for four in Old Town Marblehead. Barbeque on the backyard patio, then explore the very best of Salem right outside of your doorsteps.


Denis, Massachusetts

Featured in Boston Globe Magazine, this modern and minimalist space is within walking distance of the beach. Grab the canoe and kayaks provided by the host, and start exploring.


Boston, Massachusetts

In the swanky Back Bay neighborhood, this one-bedroom apartment is perfect for two. Explore the designer boutiques, galleries, and cool cafes right outside of your door from this dream base.


Salem, Massachusetts

Just off Essex street, you’ll feel like you’ll like you’ve stepped back in time.  With room for four, this quirky space is inspired by a Victorian British library.


Provincetown, Massachusetts

This cozy Victorian cottage has a dream location amongst the best restaurants and shops in Provincetown and, within less than five minutes’ driving, you can be on some of the most beautiful beaches in Massachusetts.


Lake cottage airbnb wrentham massachusetts

Wrentham, Massachusetts

This lovely three-bedroom cottage is just 35 minutes from Boston and 30 minutes from Providence. Constructed in 1905, this home will have you in her center of all the best options.


Want to keep on exploring? Keep on driving north then check out the Ultimate Guide to Visiting the Maine Coast.

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