Like any good New England state, Massachusetts offers up one main metropolitan city—Boston—and a whole lot of stunning middle-of-nowhere for outdoor adventuring. From bordering New York to the west, and the open ocean to the east, there's no lack of things to do, people to see, and places to go—including access to arguably some of the best seafood in the US.
In Western Massachusetts, the rolling hills of the Berkshires are perhaps best known as a remote hub for summering New Yorkers and Bostonians, with access to mountain hiking trails, skiing, a buzzy arts culture, and some pretty solid bouldering, too. On the other side of the state, the coast offers quintessential nautical New England charm, and hot spots like Provincetown, Martha's Vineyard, Cape Cod, and Salem are popular destinations for a refresh-by-the-sea.
To celebrate this historic state, we gathered up the best Massachusetts Airbnb rentals and more from east to west, including oceanside cottages, woodland cabins, mountain chalets, and more for exploring the diverse terrain and charming towns Mass has to offer.
The 20 Best Cabin Rentals & Airbnbs in Massachusetts
Iconic Cabin — Sandisfield, MA
Vibe: Mega Cabin
Bring your friends or the fam to this massive cabin outside of hot spots like Tanglewood, Great Barrington, and Otis. Not only is there an indoor endless swimming pool, yoga room, game room, full kitchen with coffee maker, multiple lofts, full baths, huge stone wood-burning fireplace, office with wifi for WFH, outdoor seating area, and deck–it's perfectly rustic and cozy. Ideal!
Rate: $775/night
Glass Treehouse — Otis, MA
Vibe: Fancy Fishbowl
Treehouses tend not to disappoint, and this one is no different. Completely secluded, spend a weekend washed in the colors of the season and the calming natural material palette of this fish-bowl. With 300 degrees of windows, an open floor plan and vaulted ceilings, this unique industrial meets nature-lover aesthetic will keep you feeling comfy as can be. Upper Spectacle Pond is a walk away or make the drive to nearby ski areas and quaint New England towns.
Rate: $296/night
Come Back Cottage — Provincetown, MA
Vibe: Peace in Ptown
This unique stay is located within walking distance to Bay Beach and the center of Provincetown, but set on a secluded patch of land. Rustic and cozy, it features artistic touches and a homey feel, so you'll be sure to "come back" soon.
Rate: $195/night
Divine Inspiration Cabin — Great Barrington, MA
Vibe: Pattern Play
Just a 5-minute drive from downtown Great Barrington, this colorful house rental features four bedrooms and three bathrooms that overlook the property’s garden. There's plenty of lounge areas, including a charming breakfast nook and a private deck for relaxing outdoors. Other highlights include a soaking tub and a wood-stove and outdoor fire pit.
Rate: $830/night
Waterfront Artist Cottage — Provincetown, MA
Vibe: A Secret Garden
Sitting atop a dune with ocean views overlooking a private beach, this modest beach cottage is the perfect solo escape or couple's retreat. Highlights include an outdoor shower, a wood-burning stove, a quick minute walk to the beach, and a claw-foot tub.
Rate: $232/night
All Season Berkshires — Dalton, MA
Vibe: Colorful and Classic
This stately home accommodates eight guests within boldly colored walls. With mid-century furnishings, a towering sun room, multiple living spaces, outdoor pool, and fire pit, this a great space for entertaining or a group trip.
Rate: $480/night
Cozy Stockbridge Cabin — Stockbridge, MA
Vibe: Cozy and Casual
Dating back to the 1940’s, this cabin offers a rustic coziness with its exposed post-and-beam structure. Best for warmer months, the cabin is a short walk to the shores of Stockbridge Bowl lake for boating or hanging out on the beach. While you could easily spend all your time hanging out on the expansive, multi-level deck, nearby Monument Mountain has great hiking, and local attractions like the Berkshire Botanical Gardens, Edith Wharton’s estate The Mount, and the town of Stockbridge offer-up plenty of sight-seeing.
Rate: $429/night
Lake Ashmere Cabin — Hinsdale, MA
Vibe: Lake House Luxe
Recently renovated and just a two-minute walk from Lake Ashmere, this modern cabin is fit for a comfortable, family-friendly stay in all four seasons. Try boating, kayaking, or picnicking in the summer, and ice-fishing and snowmobiling in the winter, then come home to the jacuzzi or cozy interior.
Rate: $224/night
Lakeside Cottage — Egremont, MA
Vibe: Unique Outpost
Unique and stylish, this lakeside cabin is close to plenty of outdoor attractions for all seasons, including Jug End State Reservation, Bash Bish Falls, Ski Butternut, and waterfront access within walking distance. Inside, there's a gas fireplace, a loft space above the living room, and mid-century meets industrial meets rustic design.
Rate: $250/night
Gift of the Sea — Nantucket, MA
Vibe: Fisherman's Delight
Built in the 1800's as a fisherman's shanty, this oceanfront short-term rental cottage retains the charm of years gone by with contemporary upgrades for a comfortable stay. A deck is a perfect place to catch some sun and take in the water views, while inside, antique and rustic furnishings make for cozy nights.
Rate: $1,598/14 night min
Autocamp Cape Cod — Cape Cod, MA
Vibe: Glamping by the Sea
A short bike to the oceanside towns of Falmouth and Woods Hole, Autocamp Cape Cod features characteristic Airstreams, Glamping Tents, and Cabins on a stunning campus overlooking Buzzards Bay. While the glampsite has plenty to do, the Shining Sea Bikeway offers walking and biking access to town and the nearby blustery beach.
Rate: $170/night
Long Pond Cabin — Plymouth, MA
Vibe: Fishing Camp
On the shores of Long Pond, this cluster of four cabins harkens back to their original 1930s fish camp character with antique furnishings and exposed wood finishes. "Dick's Cabin" features just two quaint rooms with a screened-in porch and soaking tub in the bathroom for a romantic getaway, writer's retreat, or solo trip. Outside, a shared dock is the perfect place to cast a line
Rate: $220/night
Charming Cabin — Williamstown, MA
Vibe: Cottagecore Dreams
Live out your cabin fantasies in this rustic and cozy log cabin built in the 1940's and recently renovated. Details like a claw-foot tub, vintage board games, and Victorian-inspired furnishings make it all the historical, but you'll have easy access to nearby Hancock for contemporary small-town offerings.
Rate: $235/night
Getaway Boston — Epsom, NH
Vibe: Escape the City
This Getaway glampsite might be in New Hampshire, but it caters to city-dwellers looking to escape Boston for a night or two. Offerings included a kitchenette, queen bed, hot shower, picture window, and private fire pit, and easy access to the hiking trails at Epsom Town Forest up the road.
Rate: $179/night
(Use discount code FIELDMAG for $25 off any booking)
Tree House — North Egremont, MA
Vibe: Group Trip
In the Southern Berkshires, this woodland cabin features double-height ceilings and a sprawling open floor plan for a serious group hang. Multiple decks and a wood-burning stove are great gathering places, and Great Barrington is only an 8-minute drive away for shopping and restaurants.
Rate: $443/3 night min
Sea Urchin Escape — Cape Cod, MA
Vibe: Nice and Nautical
A quintessential New England beach house, this vacation rental in Cape Cods' famed Provincetown makes for a refreshing stay. Filled with nautical decor and surrounded by views of the ocean, embrace your inner coastal grandmother for a weekend.
Rate: $948/3 night min
Otis Cabin — Otis, MA
Vibe: Rustic Charmer
Built in the 1980’s, this unique cabin is full of interesting nooks and crannies. An open floor plan, lofted second floor, and plenty of windows make the space inviting, and the central wood stove assures you’ll stay warm and cozy during your stay. A new and well stocked kitchen is great for indulgent cooking and a desk area is there if you need to check in on emails. Hiking trails and a swimming pond is a short walk away for summer visits with snowshoeing and cross-country skiing trailheads located right across the street.
Rate: $167/night
Overbrook Cabin — Monterey, MA
Vibe: By the Brook Bliss
Hike down into the hollow that houses this quintessential New England cabin. Sitting alongside a flowing stream, this charmer features vaulted ceilings, skylights, a large stone fireplace, and a tasteful combo of antique and MCM furnishings. A king bed awaits in a loft, while downstairs, two quaint bedrooms could house friends or family. There’s even a clawfoot tub for those who enjoy a nice soak. And outdoors, a deck for wild life and star spotting. Butternut and Catamount Ski areas are close by, as well as the charming town of Great Barrington.
Rate: $229/night
Urban Cabin — Lee, MA
Vibe: Barnhouse Bliss
A more modern rental, this 8-guest home mixes farmhouse, contemporary, and more modern aesthetics to create a country escape with urban loft sensibilities. Two spa-like bathrooms (hello stand-alone bathtub and rain-shower room thing), lofted area with two full-sized Murphy beds, screened in porch, double-height ceilings, spacious kitchen, and outdoor patio are the highlights here, made all the better by the surrounding trees. As always, Berkshire activities are within short drives, so it’s a great spot for a family or group trip.
Rate: $281/night
1875 House — North Adams, MA
Vibe: New England Nice
For those looking to soak in some New England history, this modernized cabin built in 1875 will do the trick. Located in the heart of North Adams, this town home offers up easy access to the restaurants and attractions the town has to offer, while providing your own little oasis. Furnishings are a pleasant mix of modern cottage, Instagram-blogger, and MCM, with a spiral staircase to round it out. Pet-friendly, let your pup roam free in the fenced-in backyard while you chill on the deck.
Rate: $120/night
Published 11-16-2020
Updated 07-03-2023
