10 Best Airbnb Rentals in Massachusetts

by D.T. Christensen
Updated June 08, 2023

best massachusetts airbnb rentals
Photo: Airbnb

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Despite being one of the smallest states in the country, Massachusetts is home to fabulous getaways, from mountain retreats in the Berkshires to breezy trips along the coast.

To those who’ve explored The Bay State’s striking coastlines, rolling hills, and bustling cities, it’ll come as no surprise that Rough Guides included Massachusetts on their list of best places to travel in 2020.

Massachusetts is easy for anyone on the eastern seaboard to reach, especially those in New York, who can take a leisurely train ride to Boston and spread out from there. But if Massachusetts is too far from you for a weekend getaway, you won’t regret spending a whole week here – between outdoor recreation, American history, and waterfront adventures, there’s plenty in the state to fill your days.

Ready to plan? Here are 10 of the best, coolest, and most unique Massachusetts Airbnbs – there’s something for every type of traveler, budget, and adventurer on this list.

Related Read: 7 Spectacular Weekend Road Trips from Boston, Massachusetts

1. Octagonal Treehouse

Octagonal Glass Treehouse MA
Photo: Airbnb

Why you should stay: Spectacular views of the Berkshires from a one-of-a-kind home.

  • Location: Otis
  • Sleeps: 4
  • Minimum stay: 2 nights
  • Rates from: $264/night

What better way to take in seven acres of wooded land in the Southern Berkshires than through floor-to-ceiling glass walls in an octagon-shaped Airbnb? There’s not a bad seat in the house, especially around the living room’s Scandinavian-style wood-burning fireplace. Venture outside and you’ll find a private deck with fire pit and comfortable dining and lounge seating for meals – or post-meal naps.

Any season’s a good time to call this unique Airbnb your temporary home: spring and summer are ideal for hiking, fall brings brilliant New England autumn colors, and winter’s the perfect time to ski nearby Otis Ridge.

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Related Read: 12 Magical Glamping Destinations in New England

2. The Writer’s Retreat

The Writer's Retreat
Photo: Airbnb

Why you should stay: Pay homage to the literary giants of Massachusetts at this lakeside cottage.

  • Location: Orange
  • Sleeps: 2
  • Minimum stay: 3 nights
  • Rates from: $131/night

A stay at The Writer’s Retreat may not transform you into the next Thoreau or Alcott, but it will transport you to a slower pace of life on Tully Pond. Hike nearby Tully Mountain Loop or Tully Lake Loop to connect with your inner transcendentalist, or take a kayak out to catch sunrise on the pond’s tranquil waters.

The cottage’s 325 square feet offers just enough space to relax and create, depending on your mindset, and if you need the inspiration, check out the small library and writing-themed decor throughout the home. If writer’s block really has you stuck, the host’s family runs New England Sweetwater Farm and Distillery about 15 miles north of the pond.

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Related Read: 10 Terrific Tiny House Rentals in Massachusetts

3. Silo Suite

silo suite airbnb
Photo: Airbnb

Why you should stay: Breathtaking views of Western Mass on a gorgeous 75-acre property.

  • Location: Williamstown
  • Sleeps: 2
  • Minimum stay: 2 nights
  • Rates from: $175/night

You’d be forgiven for thinking the most unique part of this Airbnb stay is sleeping in a renovated (and extremely clean) silo. But most guests leave knowing the Silo Suite at Bloom Meadows has some of the best views in Western Mass.

From the silo’s second-story deck, you’ll have panoramic views of endless hills and meadows. They’re impressive in any season but downright awe-inspiring in the fall, which books fast.

For a closer look at the foliage, check out the trails and lawn spaces around the immaculate grounds of Bloom Meadows, located near the New York state line. And if those views aren’t enough, take a quick drive east to Mount Greylock, the state’s highest peak at 3,941 feet.

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Related Read: 10 of the Best Airbnbs on Cape Cod, Massachusetts

4. Slate House

Slate House MA airbnb
Photo: Airbnb

Why you should stay: Private, high-end home in one of the Cape’s most scenic communities.

  • Location: Chatham
  • Sleeps: 9
  • Minimum stay: 2 nights
  • Rates from: $350/night

Preservation land around Slate House makes this Cape Cod Airbnb feel removed from the busyness of the area, and the views of Frost Fish Creek from around the home bring even calmer vibes. The best views of the water come from the outdoor fire pit area or screened patio, but even inside, you can catch stunning scenes through the living room and kitchen windows.

Slate House gets its namesake from the home’s blue slate floors, an appealing contrast to the bright, white walls and ceilings that make this such a cheery Airbnb. While most guests remark on the home’s views, it’s the rental’s design scheme – think Pottery Barn meets coastal cottage – that makes this place feel like a home away from home.

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Related read: 11 Things to Do in Oak Bluffs, Martha’s Vineyard

5. Renovated Farmhouse

modern farmhouse airbnb MA
Photo: Airbnb

Why you should stay: A modern farmhouse blending country charm with updated design trends.

  • Location: Egremont
  • Sleeps: 4
  • Minimum stay: 2 nights
  • Rates from: $350/night

This Western Mass farmhouse was renovated by David E. Lanoue and team, a firm dedicated to preserving traditional building methods with modern design in mind.

That is to say, this isn’t your traditional farmhouse rental: high-end appliances, bright rooms, and practical living areas make this one of the most popular farmhouse stays in the state. Skylights pour light onto wood floors and the all-white walls and ceilings are broken up by elegant wood beams in all the right places. The home is also quite close to Great Barrington, one of cutest small towns in the Berkshires.

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Related Read: 10 of the Best Airbnbs in Boston, Massachusetts

6. Hillcrest Cottage By The Sea

Hillcrest Cottage By The Sea
Photo: Airbnb

Why you should stay: Renovated ocean cottage in one of Massachusetts’ most underrated beach towns.

  • Location: Nahant
  • Sleeps: 6
  • Minimum stay: 2 nights
  • Rates from: $275/night

Nahant is an under-the-radar coastal town on a square-mile peninsula north of Boston, and home to this delightfully renovated 120-year-old sea cottage. It’s within walking distance of several beaches in the area, including the main drag at Nahant Beach.

The cottage’s 1,200 square feet feel much bigger than that thanks to an open-air living room and lofted bedroom,. This Airbnb is also ideal for kids and pets, thanks to an enclosed yard. It’s also a practical base for hitting tourist draws in the area: it’s a 30-minute drive to downtown Boston and 20 minutes north to Salem, with no shortage of coastal spots to explore as you wind up toward Gloucester.

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Related Read: 5 Best Day Trips From Boston for Scenic New England Getaways

7. 600 West

Berkshires Retreat airbnb
Photo: Airbnb

Why you should stay: Urban touches on a country home making for a cozy study in contrasts.

  • Location: Lee
  • Sleeps: 8
  • Minimum stay: 2 nights
  • Rates from: $287/night

Bold red doors and a tile mosaic greet you at the entrance of 600 West, a simple-yet-luxurious Airbnb located between Lee and Stockbridge in the Berkshires. They’re the first signs you’ve entered into a tastefully designed and magazine-worthy home that’s as functional as it is pretty.

Each bedroom is purposefully decorated and the loft area – with its dual murphy beds and ladder to a secret nook – is the perfect place to let the kids unwind while preparing meals in the airy, open kitchen. The home balances farmhouse style and sleek, urban details in a way that’s hard to appreciate from pictures alone.

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Related Read: What to See on a New York to Boston Road Trip Filled With History

8. Oak Bluffs Gingerbread House

marthas vineyard oak bluffs gingerbread house airbnb
Photo: Airbnb

Why you should stay: A historic cottage island retreat that’s as relaxing as it is photogenic.

  • Location: Oak Bluffs, Martha’s Vineyard
  • Sleeps: 7
  • Minimum stay: 2 nights
  • Rates from: $249/night

The ornate Gingerbread homes of Oak Bluffs date back to the 1800s, when Methodists visited the island for seasonal retreats and – we can only assume – some under-the-radar dancing. Temporary tents were eventually replaced with 500 intricately decorated cottages, and today, you can rent one of the island homes for an unforgettable Martha’s Vineyard retreat. Without a doubt, it’s one of the most adorable Massachusetts Airbnbs in the area.

The cottage is near the island’s main drag, and the Oak Bluffs town beach is a short walk away. Summer’s the best time to visit as things start to shut down after Labor Day, but it’s also the most expensive. The rental comes with all the character you’d expect of an 1800’s-era cottage. Though it’s near the Vineyard’s most popular avenues, its location in the Wesleyan Grove Historic District keeps things peaceful, even during the summer rush.

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9. South End Penthouse

boston south end brownstone airbnb rental
Photo: Airbnb

Why you should stay: A luxurious getaway in one of Boston’s most diverse neighborhoods.

  • Location: Boston
  • Sleeps: 4
  • Minimum stay: 5 nights
  • Rates from: $400/night

Ditch the hotels in the Back Bay for a penthouse stay in the South End, where you’ll get more space and killer views of Boston from your very own rooftop deck. The brownstone’s interior is elegantly appointed and both bedrooms offer views of Boston’s signature skyscrapers.

The home’s within walking distance of the area’s best eats, but if you need help making the most of your time in the city, host Susan is ready to help. It’s an excellent Airbnb if you’re a first-time visitor to the city.

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Related Read: 10 Chill Romantic Getaways in Massachusetts

10. Mill Pond Peninsula

Massachusetts private peninsula airbnb
Photo: Airbnb

Why you should stay: Waterfront views from a private peninsula in Berkshire County.

  • Location: Sheffield
  • Sleeps: 9
  • Minimum stay: 3 nights
  • Rates from: $350/night

Waterfront Massachusetts Airbnbs are a dime a dozen, but few lay claim to their own private peninsula. That’s exactly what this private Berkshires rental offers: a quiet slice of Mill Pond all to yourself.

The home was built for its surroundings, with wide, open rooms showcasing waterfront views from just about every angle. Outside, the kayaks, canoe, and dock offer a relaxing waterfront experience in any season, though fall colors make an October getaway here unforgettable.

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