This post has been updated to include a roundup of my favorite boutique properties and vacation rentals 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!
And don’t miss my round-up of the best hotels in Boston, if you’re spending some time in the city!
Modern Waterfront Getaway
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.
BOOK HERE
Chatham Cottage
Chatham, Massachusetts
This studio cottage is fitted with a queen bed, a full bath, and a charming kitchenette. The backyard area is an ideal hangout spot with a brick patio and pergola—complete with a grill—and an outdoor shower for after the beach.
BOOK HERE
Riverfront Getaway
Chester, Massachusetts
This two-bedroom tranquil oasis in Chester overlooks the river and will make you feel right at home. Lounge on the deck, soak in the warmth of a hot tub, then just lie in bed and listen to the water flowing by.
BOOK HERE
Seaside Haven
New Seabury, Massachusetts
This classy beach house has been completely renovated and has magnificent views of the ocean. It’s also just steps away from a private beach—doesn’t get much better than that, does it?
BOOK HERE
Seaside Haven
New Seabury, Massachusetts
This classy beach house has been completely renovated and has magnificent views of the ocean. It’s also just steps away from a private beach—doesn’t get much better than that, does it?
BOOK HERE
The Writer’s Retreat
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.
BOOK HERE
Nature Reserve Tiny House
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.
BOOK HERE
Octagonal Glass Treehouse
Otis, Massachusetts
This treehouse in the Berkshires is truly breathtaking. From the jaw-dropping vistas to cozy fireplaces to the chic designer touches, this place impresses at every turn.
BOOK HERE
Eliza Cottage
Nantucket, Massachusetts
Dream of a Nantucket getaway? This quintessential Nantucket home overlooks the harbor, along with Children’s Beach and Park. It’s located next door to White Elephant and just a five-minute stroll to Main Street.
BOOK HERE
Secluded Cabin Next to a Babbling Brook
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.
BOOK HERE
Cottage off Main Street
Nantucket, Massachusetts
This charming cottage in the heart of the historic district on Main Street in Nantucket sleeps up to 6.
With the outside blooming with roses and hydrangeas and a lovely patio dining area, you’ll want to spend hours in the garden after days wandering the town.
BOOK HERE
Rustic Berkshire Getaway
Otis, Massachusetts
Just outside of Jacob’s Pillow, this two-bedroom rustic space has stunning views from the spacious outdoor porch.
BOOK HERE
High Tide Cottage
Ipswich, Massachusetts
Would you take a look at this hidden gem! Located on a small island (or rather a peninsula) called Little Neck in Ipswich, this place is such a dream.
Little Neck is a gated, private community where you can step back in time and relax with your family.
The 100-year-old cottage sleeps up to 8 and has been updated with all modern amenities. Plus, the beach is just about 100 yards away! You’ll have access to a kayak, a dock, and two kids’ playgrounds, along with views of the beach and sand dunes from every room.
BOOK HERE
Modernized Historic Home
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.
BOOK HERE
Dogtown Cabin at Applecart Farm
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.
BOOK HERE
Quaint Private Garden Cottage
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.
BOOK HERE
Enchanted Tiny Tower at Santarella Gardens
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.
BOOK HERE
Gorgeous Oceanfront Penthouse
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.
BOOK HERE
Ocean View Unit with Private Roof Deck
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.
BOOK HERE
Authentic Rustic Single Family Home in Old Town
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.
BOOK HERE
Two-Bedroom Cape Cod Cottage
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.
BOOK HERE
Central Boston One-Bedroom
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.
BOOK HERE
Quintessential Salem Gothic Home
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.
BOOK HERE
Pet-Friendly Cottage
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.
BOOK HERE
Charming Lake Cottage
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.
BOOK HERE
Want to keep on exploring? Keep on driving north then check out the Ultimate Guide to Visiting the Maine Coast.
Thank you for sharing amazing information and photos. I love your all blogs. This place is so beautiful.
Thanks so much!