15 Best Airbnbs in Massachusetts, USA (2022 Edition)

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From the vibrant city of Boston to the stunning shoreline of Cape Cod, Massachusetts is one of the most exciting destinations on the East Coast. In addition to the popular metropolitan and beachside attractions, the state is overflowing with charming towns, historic sites, and incredible cuisine. Step back in time with a trip to Salem, the witchcraft capital, or enjoy the natural scenery of the vast farmland and thick forests. No matter what your interests are, you’re sure to have a great time in Massachusetts. 

In a state with so much to offer, there is an overwhelming array of accommodations to choose from. To help simplify the process of finding the perfect rental, we’ve created this list of the best Airbnbs in Massachusetts. To ensure that these Airbnbs are outstanding and consistently well rated, all of the rentals listed are run by superhosts – hosts with a proven track record of providing exceptional hospitality.

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Octagonal Glass Treehouse in the Berkshires

Kicking off our list is a cabin rental in Massachusetts that offers a unique and peaceful stay in the secluded woodlands. 

This modern treehouse features floor-to-ceiling windows in every room that provide fabulous views of the surrounding nature. The interior boasts wood-planked ceilings, rustic exposed beams, and a chic spiral staircase leading up to the main living area. There is one bedroom with a queen-size bed and an en suite bathroom, and the second full bathroom and the daybed in the living room make the space suited for up to four guests. The focal point of the living room is the red wood stove, which will keep you warm and cozy in the colder months. The open-concept space also features a comfortable sitting area, a full kitchen, a dining area, and a small library. 

Surrounded by seven acres of woods, this Massachusetts Airbnb has a spacious back deck with outdoor seating, a grill, and a stylish modern firepit. Guests can enjoy a leisurely stroll to the nearby Upper Spectacle Pond, explore the property, or take a short drive to the neighboring town of Otis. 

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Sweetwater Writer’s Retreat

Rent a house in Massachusetts that offers the best of the state’s beautiful natural scenery and tranquil wilderness. 

Perfect for writing, fishing, kayaking, or just relaxing, this cozy waterfront cottage is an ideal choice for a solo nature enthusiast or a couple, and guests can feel free to bring their furry friends. The interior is charming and rustic with wood finishes and modern comforts. The home offers one full bathroom and one bedroom with a queen-size bed, a Smart TV, and porch access. There is a comfy bench seat in the living area that faces a wall-mounted Smart TV and a set of sliding glass doors that provide fantastic views. The space also features bar-style seating, a small library, and a full kitchen. Additional amenities include Wi-Fi, air-conditioning, and a washer and dryer. 

Outside you’ll find a cozy firepit and a furnished back porch that offers great views of the Tully Mountains. The home is located right on Tully Pond, a great spot for fishing and wildlife spotting. For serious swimming and water sports, guests can walk over to the nearby Tully Lake. 

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Modern Waterfront Getaway

This stylish Airbnb in Chatham, Massachusetts offers panoramic views of Frost Fish Creek and a vast assortment of modern amenities. 

With picturesque windows, dreamy skylights, and white furnishings, the interior exudes luxury at every turn. A great choice for larger groups, the three-bedroom, two-bathroom home can accommodate up to nine guests. The main bedroom is furnished with a queen-size bed, and there are two more bedrooms with one queen-size bed and five single beds between them. The open living area offers an indoor fireplace bordered by exposed brick, a cozy sofa, a Smart TV, and a formal dining table. In the kitchen you’ll find granite countertops, stainless-steel appliances, and additional seating at the breakfast bar. Guests can enjoy many convenient amenities, including Wi-Fi, air-conditioning, a washer and dryer, a dedicated workspace, and an outdoor shower. 

Outside you’ll find a screened in porch with plenty of seating and a brand-new hot tub. The backyard offers a firepit with two Adirondack chairs and unrivaled views of the pond and its surrounding nature. 

Chatham is a charming town located in Southeast Cape Cod, and this Airbnb in Massachusetts boasts a prime location close to several beaches, restaurants, resorts, and shops. 

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Related: 15 Best Airbnbs in Cape Cod, MA

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Modern Farmhouse Near Great Barrington

For a conveniently located rental with a charming country design, check out this Massachusetts Airbnb near Great Barrington. 

Recently renovated, this sophisticated home is spacious and luxurious. It offers two bedrooms and two bathrooms, making it suited for up to four guests. The first floor bedroom is furnished with a queen-size bed and offers a connected bathroom and laundry room. Upstairs, you’ll find the master suite, which boasts a stylish combination of white and wood décor, a king-size bed, and an en suite bathroom with a jetted walk-in shower. The living room offers two leather sofas, a 55-inch TV, and grand windows that make the space cheery and bright. There is a four-person dining table in the full kitchen, which boasts stainless-steel appliances and colorful accents. 

With beautiful scenery no matter the season, the quaint backyard is another notable aspect of this vacation rental in Massachusetts. The stone patio features an outdoor fireplace, a grill, and a dining table with chairs, and guests can enjoy easy access to the nearby wildlife preserve and the hiking trails at Bash Bish Falls. 

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Silo suite in Massachusetts, USA
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Silo Suite With Berkshire Mountain Views

If you’re interested in a unique and cozy short-term rental in Massachusetts with stunning views of the rolling hillside, this is the Airbnb for you.

Unplug and relax with this luxuriously renovated silo at Bloom Meadows. The home offers a king-size bed and a three-quarter bathroom, making it a great choice for a solo adventurer or a couple. Several windows make the space beautiful and bright, and the glass doors in front of the bed open onto a porch that provides beautiful views. With no Wi-Fi or TV, this is the perfect place to take a break from digital distractions and fully enjoy the natural scenery and nearby activities. Comfortable amenities include air-conditioning and an indoor fireplace. 

This Airbnb in Massachusetts is surrounded by beautiful scenery and great opportunities for outdoor adventure. The home is within walking distance of the ski slopes at Jiminy Peak and zip lines at Ramblewild Adventure Park, and horseback riding is just a few steps away. 

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Tranquil Retreat on Long Pond

When it comes to house rentals in Massachusetts, you can’t go wrong with this luxurious waterfront home. The three-bedroom, 1.5 bathroom house is located in a quiet neighborhood on Long Pond and offers beautiful scenery and optimal privacy. 

The interior is well decorated with tasteful splashes of color, painted exposed brick, and modern furnishings. In every room, you’ll find large windows that provide alluring waterfront views. Up to seven guests can stay in the house, which offers two bedrooms with queen-size beds and one bedroom with a twin-over-full bunk bed. The main floor offers a spacious living room that is warm and inviting, with a ton of comfy seating, a Smart TV, and a gas fireplace. There is a separate kitchen with elegant lighting, high-end appliances, granite countertops, and a convenient breakfast bar. The formal dining room is furnished with a large table and magnificent décor, including a well-stocked bookshelf and a glimmering chandelier. 

Along with its elegant atmosphere and prime waterfront location, this rental boasts an impressive assortment of outdoor amenities. On the spacious and private deck, you’ll find two couches and an outdoor dining table, and the backyard offers a firepit, a hammock, an eight-person hot tub, and a convenient outdoor shower. The home also has a private dock, and your hosts will provide two kayaks that you can use free of charge. When you feel like venturing off the property, there are two beaches, both great for fishing and swimming, less than two miles away.

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Enchanted Tiny Tower

For a unique and exciting experience, check out this dreamlike vacation home for rent in Massachusetts. 

The two-story tower features soaring conical ceilings and grand windows that provide magical views of the surrounding scenery. The lovely space offers a canopied queen-size bed and one full bathroom, making it suited for one or two guests. This would be a great choice for a solo traveler hoping to be inspired by the storybook atmosphere or a couple looking for a romantic retreat. There is also a well-equipped kitchenette and two small sitting areas next to picturesque mill windows. Additional amenities include Wi-Fi, a TV, and an indoor fireplace. 

Located in the Berkshire Mountains, this romantic Airbnb offers garden paths, lily ponds, stone bridges, a running brook, and a firepit. 

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Historic Oceanfront Apartment

Relax to the sound of waves crashing on the shore with this Massachusetts Airbnb on the Salem seaside. 

The ground-floor apartment is completely private with its own entrance, a full kitchen, and a private full bathroom with heated floors. Large windows offer beautiful ocean views, and the living space is furnished with comfy chairs and a four-person dining table. One or two guests can stay in the apartment, which has one bedroom with a queen-size bed and a wall-mounted TV. Guests will also have access to a beautiful yard with two Adirondack chairs overlooking the ocean. 

Salem is one of Massachusetts’ most popular tourist destinations offering plenty of exciting activities and fun attractions year-round. In addition to enjoying the pristine shoreline, guests can check out art festivals, jazz festivals, witch museums, and a diverse array of historical sites. 

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Romantic Oceanfront Apartment Near Boston

If you’re looking for a seaside Airbnb near Boston, Massachusetts, this is the perfect rental for you. The elevated hilltop location allows for stunning ocean views from every room in the apartment. 

The interior is large and luxurious with cathedral ceilings, skylights, and modern appliances. Ideal for one or two guests, the space is perfect for a romantic couples retreat. The bedroom offers a queen-size bed, a window seat, and a dedicated workspace. There is also an en suite bathroom with a Jacuzzi tub and a wall of glass doors that offer porch access and allow you to admire the views while lying in bed. Enjoy meals at home with a separate chef’s kitchen and a formal dining room decorated with a grand piano and cheerful indoor plants. The living area offers several comfy seating options, an indoor fireplace bordered by exposed brick, and a full wall of windows. Additional amenities include Wi-Fi, an extra half bathroom with a washer and dryer, and complimentary breakfast provided on the first night of your stay. Outside you’ll find a wrap-around porch with a private hot tub and panoramic views. 

In addition to its luxurious amenities and stunning views, this rental’s prime location makes it one of best Airbnbs in Massachusetts. Situated 12 miles away from Boston, this apartment is perfect for anyone looking for a peaceful retreat in close proximity to the city. Guests can also find several beaches, restaurants, and shops within walking distance of the home. 

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Related: 15 Best Airbnbs in Boston, MA

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Private Peninsula Retreat in the Berkshires 

This cabin for rent in Massachusetts boasts a completely private location and endless outdoor activities. 

Surrounded by trees on a private two-acre peninsula, this Airbnb on Mill Pond is the perfect choice for a Zen retreat. The interior is characterized by high ceilings, wood walls, and rustic exposed beams. A great option for larger groups, the home offers two full bathrooms, two bedrooms with queen-size beds, and one bedroom with one double bed and one single bed. The full kitchen boasts high-end appliances, including a washer and dryer, and is separated from the living room by a four-person breakfast bar. The spacious living area offers cozy seating, a wall-mounted TV, and grand windows, and there is a separate dining room that also functions as a den. 

If you’re looking for a trip filled with water activities and natural scenery, you can’t go wrong with this Airbnb in Massachusetts. Beautiful year-round, the setting is ideal for kayaking, canoeing, paddle boarding, and fishing. Your hosts thoughtfully provide all necessary equipment, including life vests in a variety of sizes. Guests will also have access to an outdoor firepit, yoga mats, and four bikes. When you feel like venturing off the property, the Berkshires offer fabulous museums, theaters, and dining options. 

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Windmill Cottage

With its charming design and storybook atmosphere, this Airbnb in Cape Cod, Massachusetts, offers a unique stay and comfortable amenities. 

Recently restored, the windmill was built in the 1940s and boasts a ton of character with its nautical-themed design, large exposed beams, and warm accents. Up to four guests can stay in the rental, which offers one bedroom with a queen-size bed and a lofted bedroom with a double bed and a dedicated workspace. When you first enter the home, you’ll notice the colorful accents and high-end furnishings in the combined dining and living room. Walk further inside to check out the well-stocked full kitchen and the full bathroom with a walk-in shower. 

Outside, you’ll find a professionally landscaped lawn with beautiful greenery, a patio table, and an outdoor shower. If you’re traveling with a boat or a kayak, the property comes with a private launch on Mill Pond. Additional amenities include Wi-Fi, TV, central air-conditioning and heating, and beach essentials. The home is also pet-friendly and suitable for children, with a travel crib and baby gear provided by the host. 

Located in the historic Old Village neighborhood, the property is within walking distance of the beach and the Chatham Lighthouse. Guests can also take a short stroll into town and enjoy shops, restaurants, and the charming ambiance of Old Cape Cod. 

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Chestnut Hill Luxury Home

Book a stay in one of the most exclusive neighborhoods in Massachusetts with this historic Spanish Colonial home. 

Built in 1913, the home has undergone extensive renovations and now offers a luxurious stay with brand-new furnishings and modern amenities. The rental’s five bedrooms and 3.5 bathrooms can comfortably accommodate up to nine guests. Two bedrooms offer king-size beds, two offer queen-size beds, and the fifth room offers two single beds. Each room is spacious and bright, offering the highest quality furnishings and décor. Picturesque windows throughout the home make the common areas bright and cheery. The house offers a separate living room and sunroom, great for relaxing in front of the TV or hanging out with the family. Adjacent to the living room, you’ll find a formal dining room and a separate kitchen with wooden cabinetry and a breakfast table. Additional amenities include Wi-Fi, air-conditioning, a dishwasher, and a washer and dryer. 

The house is located on a carriage road across from Boston College and offers easy access to nearby shops, restaurants, the reservoir, and Chestnut Hill Square. 

With its rich history, elegant design, and convenient location, this beautiful home is hands down one of the best Airbnb rentals in Massachusetts. 

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Idyllic Country Retreat

Rent a cabin in Massachusetts with classic country appeal and 23 acres of land to explore. The rental is a completely separate and private studio located on the same grounds as a historic farmhouse. 

The studio offers a small kitchenette with basic supplies and appliances, and the living area is furnished with a cozy couch and a large table pushed up against a picturesque window. Enjoy lovely views of the surrounding scenery as you eat breakfast or catch up on some work. The sleeping space offers a double bed against a wall of windows looking out onto the surrounding meadows. There is also a private full bathroom located outside of the cottage and accessible by a short walk down the hill. 

The land surrounding this Airbnb in Massachusetts offers expansive meadows, beautiful gardens, and exciting woods to explore. Guests are welcome to roam the entire property and pick fruit, vegetables, and flowers in the gardens. Located 10 minutes away from Shelburne Falls, the property allows easy access to Deerfield River and a wide assortment of shops and restaurants. 

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Cheerful Cottage Near Downtown and the Beach

Unique and colorful, this charming house for rent in Massachusetts offers a peaceful stay in a private oasis. 

The fairytale cottage is surrounded by a private garden and can be recognized by its bright blue and yellow exterior. The interior is equally as attractive with white furnishings and pastel hues. Up to seven guests can stay in the home, which offers two bedrooms furnished with two single beds each, and a master bedroom with a double bed, a single bed, and fabulous gothic-style windows. The living room has a comfy couch, a wall-mounted TV, and a closet filled with books and board games. There is also a full bathroom and a spacious eat-in kitchen with high-end appliances and a large dining table. The vast assortment of modern amenities, including Wi-Fi, air-conditioning, a washer and dryer, and a dedicated work space, are sure to make you feel right at home. 

Outside, you’ll find a spacious deck with an outdoor dining table and a grill as well as a private outdoor shower. 

Located in downtown Oak Bluffs, the home is steps away from restaurants, shops, grocery stores, and vibrant nightlife. Guests can also take a short stroll to the beach, and the hosts have thoughtfully provided essential beach supplies for your convenience. 

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Luxury Seaside Suite

Wrapping up our list is a Massachusetts Airbnb that boasts a stunning interior, a convenient location, and Airbnb Plus status. For those unfamiliar with it, Airbnb Plus is an exclusive distinction reserved for stylish Airbnbs that have been verified by in-person inspection. 

This sun-drenched apartment is located just steps away from the beach and features tranquil cool-toned décor and opulent furnishings. The studio layout is suited for one or two guests, and there is a fabulous king-size bed situated next to a bay window with a separate seating area. The kitchenette offers a sink, a microwave, a minifridge, and a coffee maker, and the spa-like full bathroom is equipped with an oversized rain-style walk-in shower and glittering accents. 

The apartment is set in the small town of Beverly, a charming neighborhood located 26 miles away from Boston. In the immediate vicinity, guests can find beachfront parks, vibrant downtown streets, and several shopping and dining options. 

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Hopefully this list helps you in your search for the perfect place to stay. No matter what kind of vacation you’re looking for, a stay in one of the best Massachusetts Airbnbs is sure to make your trip remarkable.


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