The best Airbnbs in Massachusetts range from cabins and treehouses to lake houses and luxury vacation rentals on the beach. If you’re dreaming of a secluded getaway in the Bay State, just wait until you see these Massachusetts vacation rentals on Airbnb and VRBO.
In Massachusetts, you don’t have to travel far to find unique Airbnbs, including log cabins, treehouse rentals, and beach and lake houses in Massachusetts! From Boston, Cambridge, and Cape Cod to the Berkshires in Western Mass, there are so many unique destinations within a couple hour’s drive, covering everything from historic sites to nature getaways. And what better way to experience this beautiful state than by staying in a unique Massachusetts vacation rental?
If you’re looking for a respite from work life and to let go of all of life’s worries, Massachusetts has got you covered. This article covers the best lodging in Massachusetts, which includes Airbnbs, VRBOs, and cabins for rent in Massachusetts. Here’s my round-up of the 20 best Airbnbs in Massachusetts, each with plenty of availability and cool amenities, including swimming pools, hot tubs, stunning views, and more!
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The Coolest Airbnbs in Massachusetts: Top Vacation Rentals in 2021
Here are the best Airbnbs in Massachusetts by category, taking into account different amenities, trip types, and budgets. The following sections will cover each listing, and other top vacation rentals, in more detail.
Top Airbnb in Massachusetts: Modern Vacation Rental in Martha’s Vineyard
Best Luxury Rental Massachusetts: Classic Wellesley House
Top Romantic Airbnb in Massachusetts: Secluded A-Frame Airbnb
Best Airbnb in MA for Large Groups: Gloucester Condo on the Ocean
Best Cheap Airbnb Massachusetts: Beachfront Cottage on a Pond
Coolest Treehouse Airbnb in Massachusetts: Enchanted Tiny Tower at Santarella Gardens
Best Cabin Rental MA: Traditional Log Cabin on the Cape
Top Airbnb Massachusetts with a View: Hilltop Haven in Western MA
Best Winter Airbnb Massachusetts: Modern Rental in the Berkshires
Best Lake House Rental in MA: Lakefront A-Frame Home
Most Unique Airbnb in Massachusetts: Exotic Spanish Colonial Home
20 Best Airbnbs in Massachusetts
If cabins, treehouses, romantic lake houses, and luxury vacation rentals on the ocean in Massachusetts all sound good to you, you’re in for a treat! Here are some of the most unique stays in Massachusetts in 2021.
Note: The properties below are featured on both Airbnb and VRBO. For each listing, I’ve only included the link to the website with the cheapest rates.
1. Enchanted Tiny Tower at Santarella Gardens
Location: Lee, Massachusetts
Rates from: $235 per night
Accommodates: 2 guests
This romantic Airbnb treehouse in Massachusetts will feed your imagination. It’s set on the Santarella Estate in the Berkshires, one of the coolest vacation destinations in New England. You’ll be within reach of the best lakes, hiking trails, and scenery that Western Massachusetts is known for.
Walk around this 4-acre property, filled with gardens, woods, and a pond, and you’ll see why this is among the coolest Airbnb rentals in MA!
Unique features: Cozy and unique Airbnb treehouse; 35 ft. conical ceiling; canopied bed; brook and pond on property; gardens; chimenea with firewood
Cool sights nearby: October Mountain State Forest | The Mount Edith Wharton’s Home | Berkshires Scenic Railway Museum | Stockbridge | Lee | Tanglewood Music | Benedict Pond
2. Old Village Windmill Cottage – One of the Most Unique Airbnbs in Massachusetts
Location: Chatham, Massachusetts
Rates from: $170 per night
Accommodates: 4 guests
Experience the charm and allure of Massachusetts from this windmill Airbnb in Chatham. This historic property is a part of Chatham’s Old Village neighborhood, just a short walk to the beach and downtown.
Enjoy the custom-built features inside this vacation rental, which exude personality. From the historic craftmanship to the warm and cozy furniture, it’s no wonder this is among the coolest Airbnbs in Massachusetts.
Unique features: Classic Cape Cod windmill accommodation; nautical features; spacious living room and bedroom; loft area; great location within walking distance of the beach and downtown
Cool sights nearby: Cape Cod National Seashore | Chatham Lighthouse | Monomoy Island | Lighthouse Beach | Atwood Museum | Ridgevale Beach
3. Beautiful Beach House Rental in Massachusetts on Cape Cod
Location: Barnstable, Massachusetts
Rates from: $455 per night
Accommodates: 10 guests
“One of a kind extraordinary waterfront rental. Wake up to the most spectacular views of the Ocean and enjoy watching the sun set over the Kennedy Compound. Build sand castles on your own private beach while watching sail boats set off to Nantucket. This home is quintessential for a family vacation or romantic getaway.” – Airbnb
If you’re looking for a secluded beach vacation with your family or friends, this is the perfect home base on Cape Cod!
Read next: 17 Cool Rentals in Cape Cod
Unique features: Ocean views; 100 ft. of private beach; outdoor grill; outdoor shower; beach deck; patio
Cool sights nearby: Craigville Beach | John F. Kennedy Hyannis Museum | Mayflower Beach | Edward Gorey House | Sandy Neck Lighthouse | Main Street | Cape Codder Water Park
4. Secluded A-Frame Cabin Rental in Massachusetts
Location: Becket, Massachusetts
Rates from: $162 per night
Accommodates: 6 guests
“Pack your bags and gear up for an outdoor adventure courtesy of this spacious Becket cabin, boasting easy access to State Parks, breweries, lakes, and more! With 2 bedrooms and 1 bathroom, there’s room for the family or your group of friends to tag along! You’ll love having your own yard space equipped with a fire pit, dining area, and patio furniture. Enjoy days on Little Robin Lake just steps from this vacation rental, or visit nearby attractions like Ashintully Gardens or Becket Quarry!” – Airbnb
Looking for an a-frame cabin with treehouse vibes in Massachusetts? You’ll love this vacation rental in Western MA!
Unique features: A-frame cabin; treehouse vibe with lake views; patio; fire pit; deck and Adirondack chairs; gas grill; foosball table
Cool sights nearby: October Mountain State Forest | Stockbridge | Lee | Tanglewood Music | Becket Land Trust | Chester-Blandford State Forest | Otis Reservoir | Becket Quarry
5. Enchanting Loft Cottage with Private Deck – A Budget-Friendly Airbnb Rental in Massachusetts
Location: Barnstable, Massachusetts
Rates from: $120 per night
Accommodates: 2 guests
Looking for a romantic getaway on the Cape? This Massachusetts Airbnb vacation rental has got you covered.
This cozy cottage is decked out with modern décor and amenities that you’d expect to find in a luxury resort. Relax on the spacious deck as you sip coffee. Marvel at at the vaulted ceilings and ship ladder staircase that leads to the bedroom. After a day at the beach, I can’t imagine a better home base than this beautiful Airbnb for rent in Massachusetts.
6. Luxury Oceanview Suite in Victorian – A Top Beach House Rental in Massachusetts for Couples
Location: Beverly, Massachusetts
Rates from: $192 per night
Accommodates: 2 guests
Looking for a romantic Massachusetts vacation rental on the ocean? This recently remodeled Victorian home in Beverly is calling your name!
Relax and rejuvenate from this beautiful seaside home with modern amenities. The sophisticated interior decor and location just steps from the beach makes this a top vacation rental in Massachusetts, hands down.
7. Chestnut Hill Luxury Home for Rent Near Boston College
Location: Newton, Massachusetts
Rates from: $695 per night
Accommodates: 9 guests
“An urban oasis! This beautiful, historical Spanish Colonial home (the John H. Johnson House, built in 1913), is located in Chestnut Hill. This lovely home has been extensively renovated for today’s modern living and is elegantly appointed with new furnishings. We are located on Mile 21 of the Boston Marathon course, just over Heartbreak Hill, and steps away from the Boston City line.” – Airbnb
This has to be one of the best luxury rentals in Massachusetts. It has a cool Spanish colonial vibe to it, with stunning interior décor and a perfect location in Newton.
With so much luxury and charm, this is definitely one of the best Airbnbs in Massachusetts, particularly for large groups!
Unique features: Historic colonial home; tall ceilings; excellent location in Chestnut Hill; indoor fireplace
Cool sights nearby: Boston College | Heartbreak Hill | Chestnut Hill Reservoir | Mount Auburn Cemetery | Emerald Necklace | Echo Bridge | Cold Spring Park
8. Modern Airbnb in Berkshire Mountains of Massachusetts
Location: Becket, Massachusetts
Rates from: $285 per night
Accommodates: 6 guests
“A new custom designed house awaits you in the Berkshire mountains. Finished in 2020, this Post and Beam retreat is on 2.7 acres and has 3+ bedrooms, 3 full baths, a large kitchen with brand new appliances and 14 foot high ceilings. Hiking trails are right out the front door.” – Airbnb
If you’re looking to venture into the mountains, you won’t want to miss out on this brand new home. This beautiful and modern vacation rental is among the coolest Airbnbs in the Berkshires, and in all of Massachusetts!
Unique features: Cozy mountain home; wraparound deck; high ceilings; perfect location near the ski slopes; dog-friendly
Cool sights nearby: October Mountain State Forest | Stockbridge | Lee | Tanglewood Music | Keystone Arch Bridges Trail | Chester-Blandford State Forest | Otis Reservoir | Becket Quarry
9. Dreamy Loft in Downtown Boston is Among the Coolest Vacation Rentals in Massachusetts
Location: Boston, Massachusetts
Rates from: $243 per night
Accommodates: 8 guests
“This beautiful apartment has exposed brick and an industrial feel, but also the warmth and comfiness of an inviting home. What makes this space unique is its history. The building hallways all show historic photos of the neighborhood dating back to the 1800s! Just steps from the Boston Common, this building has had many tenants over the decades, from retail shops to manufacturing companies!” – Airbnb
Boston is brimming with rich history and charm. Explore Boston’s restaurant scene and unique history from this amazing launchpad. You’ll be within walking distance from many of the top attractions, including the Boston Common, Boston Public Garden, and Freedom Trail. I can’t imagine a better place to experience it all than at this unique Airbnb in the heart of Boston, Massachusetts.
Unique features: Industrial-style loft in the heart of Boston; self check in; onsite security guard; laundry in unit; creative interior designs
Cool sights nearby: Freedom Trail | Boston Public Garden | Museum of Fine Arts | Faneuil Hall | Boston Common | Beacon Hill
10. Gloucester Condo with Ocean Views – One of the Best Airbnbs in Massachusetts
Location: Gloucester, Massachusetts
Rates from: $399 per night
Accommodates: 12 guests
Looking to stay at one of the best Airbnbs in Massachusetts? Look no further than this amazing vacation rental in Gloucester, MA. Here, you can wake up every morning to the sound and smell of the ocean. From its private deck, you’ll have some of the most breathtaking views of the East Coast. And it’s decked out with all the amenities you’ll need for a memorable stay in Massachusetts.
Unique features: Epic coastal views; 25×15 ft. private deck; gas fireplace; excellent location in Gloucester
Cool sights nearby: Halibut Point State Park | Hammond Castle Museum | Wingaersheek Beach | Good Harbor Beach | Singing Beach | State Fort Park
11. Hilltop Haven in Western Massachusetts
Location: Colrain, Massachusetts
Rates from: $799 per night
Accommodates: 12 guests
“Come and enjoy our country retreat with breathtaking mountain and valley views. This expanded 1770 farmhouse gives you 4,500 sq. ft. of space for large family and friends get togethers. The house overlooks the Green River Valley and at the end of a dirt road provides a quiet escape with views and vistas that are constantly changing through the seasons.” – Airbnb
If you’re looking for a secluded vacation rental tucked away in nature, you won’t want to miss out on this beautiful Airbnb in Massachusetts. With so much space for large groups, it’s also among the best vacation rentals in New England.
Unique features: Historic home with 4,500 sq. ft. of living space; swimming pool; indoor and outdoor hot tubs; views of a river valley; spacious decks; porches and patios; spa area; river access
Cool sights nearby: Green River | Arthur Smith Covered Bridge | Catamount State Forest | Eunice Williams Covered Bridge | McLeod Pond | H.O. Cook State Forest
12. Beachfront Cottage Airbnb in Massachusetts on Whites Pond
Location: Dennis, Massachusetts
Rates from: $95 per night
Accommodates: 4 guests
Enjoy acres of private pond property from this beautiful Airbnb cottage in Massachusetts. This charming home features a private beach, deck, fire pit, outdoor shower, and more, making for the perfect Cape Cod experience. If that’s not enough to convince you, the nearby beaches, restaurants, and bike paths, will!
13. Beach House Vacation Rental in Massachusetts with Hot Tub
Location: Swampscott, Massachusetts
Rates from: $229 per night
Accommodates: 2 guests
Dreaming of a romantic getaway on the ocean? This Massachusetts vacation rental in the North Shore has got you covered.
This two-level home for rent only 12 miles from Boston offers unparalleled ocean views at an affordable price. You’ll be just an easy stroll from local restaurants, shops, and beaches. However, after spending time beneath the skylights, relaxing in the Jacuzzi, and lounging on the wraparound decks, it will be hard to leave this beautiful vacation home in Massachusetts!
14. Spacious Vacation Rental Near the Beach in Martha’s Vineyard
Location: Vineyard Haven, Massachusetts
Rates from: $300 per night
Accommodates: 8 guests
“Minutes from Lake Tashmoo and the Woods Hole-Vineyard Haven Ferry, this ultra-modern 4BR home promises a relaxing getaway to Martha’s Vineyard. 2,672 square feet of upscale living space and a woodsy backyard add allure to your island retreat.” – Airbnb
I can’t imagine a more perfect Airbnb in Massachusetts than this vacation rental in Vineyard Haven. It’s brand new, decked out with all the best amenities, and located near the beach. What more could you want in a top Massachusetts Airbnb?
Unique features: Upscale home with 2,672 sq. ft. of living space; firepit; stone patio area; posh furniture and décor; expansive deck; gas grill; outdoor shower
Cool sights nearby: Tisbury Town Beach | Martha’s Vineyard Playhouse | Mink Meadows Golf Club | Flying Horses Carousel | Cuttyhunk Island | Gay Head Lighthouse
15. This Chatham Home is Among the Best Vacation Rentals in Massachusetts
Location: Chatham, Massachusetts
Rates from: $270 per night
Accommodates: 8 guests
Immerse yourself in Cape Cod living from this beautiful Massachusetts vacation rental in Chatham. It’s located just steps from the beach, offering breathtaking views of the harbor and surrounding landscape.
Take in the warmth and coziness that this accommodation emits at every turn. Enjoy the modern furniture and amenities before basking in the sun and taking advantage of the Cape. Is this one of the coolest vacation rentals in MA? Absolutely!
16. Lakefront Home That’s Among the Best Airbnbs in Massachusetts
Location: Sturbridge, Massachusetts
Rates from: $250 per night
Accommodates: 8 guests
Looking for a lake house in Massachusetts that resembles an a-frame cabin? Check this out!
This waterfront rental is situated on its own peninsula, with breathtaking views of the lake and surrounding scenery. It’s equipped with a wraparound deck, heated sun porch, private dock, and other unique amenities that will ensure a fun and comfortable stay at one of the best Airbnbs in Massachusetts. Spend a week or weekend here with a group of family or friends, and you’ll see why this is one of the best lakefront rentals in MA.
Unique features: Gorgeous views of the lake; wraparound deck; heated sun porch; patio; firepit; large yard and dock; private beach area; stone fireplace; high ceilings; rustic wooden interior
Cool sights nearby: Old Sturbridge Village | Bigelow Hollow State Park | Wells State Park | Bigelow Hollow Road | Nipmuck State Forest | Brimfield State Forest | Optical Heritage Museum
17. Beautiful Lake House for Rent in Massachusetts
Location: South Yarmouth, Massachusetts
Rates from: $278 per night
Accommodates: 7 guests
Experience the Cape in style from this beautiful Massachusetts vacation rental with a hot tub. It’s outfitted with a gas fireplace, dock for swimming and fishing, patio area, marble countertops, spacious deck, waterfront views and more.
Take full advantage of the two kayaks and SUPs available on the property. Relax and catch the sunset with a cocktail from the expansive porch seating area. With so much charm and personality, it’s no wonder this is among the best vacation rentals in Massachusetts.
18. Top Luxury Airbnb in Massachusetts
Location: Wellesley, Massachusetts
Rates from: $996 per night
Accommodates: 8 guests
“This glorious 1907 New England house, built by Katharine Lee Bates, author of “America the Beautiful,” is absolutely perfect for family and friend gatherings. Lots of beds, sitting spaces and sunny kitchen, this house is ideal for a “big chill’ weekend, or graduation and events at nearby Wellesley College, Olin, Babson, Regis and Dana Hall. We are also perfect for the Boston marathon – at exactly the halfway point, we have easy access for runners and perfect viewing for fans.” – Airbnb
Is this one of the best Airbnbs in Massachusetts? Absolutely! This historic home, decked out with modern amenities, is among the coolest vacation rentals for history lovers and bohemians alike. What more could you want in a top Airbnb rental in Massachusetts?
Unique features: Iconic New England house; huge living space; indoor fireplace; dedicated workspace; peaceful location; hammock
Cool sights nearby: Elm Bank | Warren Park | David Museum | Wellesley College Botanic Gardens | Lake Waban | Centennial Reservation | Mass Audobon’s Broadmoor Wildlife
19. Traditional Log Cabin Rental in Massachusetts that Feels Like a Treehouse
Location: Plymouth, Massachusetts
Rates from: $145 per night
Accommodates: 6 guests
“This log house is beautiful. Only minutes from historic Plymouth, beaches and the Cape. On an acre of private, wooded property. Located across the street from lovely cranberry bogs and walking trails.” – Airbnb
Looking to stay at one of the best Airbnb treehouse rentals in Massachusetts? This log cabin on VRBO and Airbnb has an elegant and cozy interior that’s among the best I’ve seen!
Unique features: Traditional log home near Cape Cod; deck with BBQ grill; views of cranberry bogs; excellent location; interior decor resembling that of a treehouse; pet-friendly
Cool sights nearby: Plymouth Rock | Mayflower II | Plymouth Plantation | Thomas Land/Edaville Amuseument Park | The King Richard’s Fair
20. Gorgeous Lake House Vacation Rental in Massachusetts on VRBO
Location: Orange, Massachusetts
Rates from: $152 per night
Accommodates: 2 guests
This lake house rental in Massachusetts is perfect for romantic getaways. It’s nestled on lake with breathtaking views of Tully Mountain in Orange, MA.
From the moment you walk inside this 4-season cottage, you’ll be amazed by the salvaged barn wood, maple floors, and custom-built furniture. Though it’s only 325 sq. ft., the space is efficiently laid out. Take advantage of the kayaks, walk-in shower, and other unique amenities at this property. If you’re seeking a romantic lake house for rent in Massachusetts, it surely doesn’t get any better than this!
Best Places to Stay in Massachusetts
Still figuring out where to stay in Massachusetts? Here are my favorite cities, towns, and nature areas where I recommend staying:
– Top Cities and Towns: Boston, Gloucester, Hyannis, Newburyport, North Adams, Provincetown, Rockport, Salem
– Best Cabins and Campgrounds: Berkshire County
– Top Regions: The Berkshires, Cape Cod, Greater Boston Area, North Shore
The Best Airbnb Rentals in Massachusetts in 2021
Have you ever stayed in a unique Airbnb vacation rental in Massachusetts? Let me know in the comments or on IG, as I’m always looking to add to this round-up of the best Airbnbs in Massachusetts!
Looking for more cool places to visit in New England? Check out these destinations:
– Coolest Airbnb Rentals in the White Mountains
– Unique Stays in Rhode Island
– Best Time of Year to Visit Massachusetts
– Coolest Airbnbs in New York State
– Most Beautiful Airbnbs in the Berkshires
– Best Places to Stay in Vermont
