As a local from the Boston suburbs, I’ve spent years exploring the best vacation rentals Massachusetts has to offer. From charming beach cottages on Cape Cod to serene lake houses in the Berkshires, and even unique treehouses tucked away in the woods, this state is full of cozy escapes.
I’ve personally stayed in countless vacation homes throughout the area, and I’m excited to share my top picks with you. Whether you’re dreaming of a coastal retreat or a peaceful getaway in nature, these 22 Airbnb rentals are perfect for your next Massachusetts adventure.
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The 22 Coolest Airbnb Rentals in Massachusetts
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 Overall: Modern Vacation Rental in Martha’s Vineyard
- Best Luxury Rental: Classic Wellesley House
- Top Romantic: Secluded A-Frame Airbnb
- Best for Large Groups: Gloucester Condo on the Ocean
- Best Cheap Airbnb: Beachfront Cottage on a Pond
- Coolest Treehouse Airbnb: Enchanted Tiny Tower at Santarella Gardens
- Best Cabin: Traditional Log Cabin on the Cape
- Top with a View: Hilltop Haven in Western MA
- Best Winter Rental: Modern Rental in the Berkshires
- Best Lake House: Lakefront A-Frame Home
- Most Unique: Exotic Spanish Colonial Home
Note: The properties below are featured on Airbnb, VRBO, Booking and Expedia. 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. Stunning Architect Designed Sun Drenched Ocean Front Cottage
Location: Mashpee, Massachusetts
Rates from: $952 per night
Accommodates: 6 guests
Imagine waking up to the gentle sound of waves and the soft glow of the morning sun. The Sun Drenched Ocean Front Cottage in Mashpee offers just that and so much more. This oceanfront gem, with its blissful views, promises a stay that’s both luxurious and rejuvenating.
The cottage boasts three spacious bedrooms, each furnished with a comfortable queen bed. Every corner of this home is designed to provide a serene escape – from the cozy interiors to the expansive deck and patio that offer breathtaking views of the ocean. Whether you’re preparing a meal in the well-equipped kitchen, unwinding in the garden, or taking a refreshing outdoor shower, this cottage promises a stay like no other.
For those eager to explore the surrounding area, the pristine Cape Cod Beaches are just a minute’s walk away. The beautiful Popponesset Beach is a mere 4-minute walk, and the expansive South Cape Beach State Park is a short 6-minute drive.
The Sun Drenched Ocean Front Cottage is not just a place to stay; it’s a journey into the heart of Massachusetts’s coastal beauty. It’s where memories are forged amidst the gentle rustle of the waves and where every sunrise and sunset becomes a moment to cherish.
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. Mahican Cabin – A Private Nature’s Reserve For 2
Location: North Adams, Massachusetts
Rates from: $275 per night
Accommodates: 2 guests
Nestled amidst the serene landscapes of North Adams, the Mahican Cabin beckons travelers seeking a tranquil escape. This private nature reserve is the epitome of rustic charm, offering a blend of comfort and the raw beauty of nature.
The cabin features a cozy bedroom with a queen bed, making it a perfect romantic getaway for two. Every corner of this home is designed to provide a serene escape – from the well-equipped interiors to the outdoor spaces that promise breathtaking views of the surrounding landscapes. Whether you’re preparing a meal, unwinding on the deck or patio, or exploring the garden, the Mahican Cabin promises a stay like no other.
For those looking to explore the area, the vibrant town of North Adams offers a range of attractions. The nearby Pittsfield Municipal Airport ensures easy accessibility for travelers. And for nature enthusiasts, the cabin’s location offers a plethora of hiking trails and scenic spots to explore.
The Mahican Cabin is not just a place to stay; it’s a journey into the heart of Massachusetts’s natural beauty. It’s where memories are forged amidst the gentle rustle of the trees and where every sunrise and sunset becomes a moment to cherish.
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. Private Lake House
Location: Lee, Massachusetts
Rates from: $564 per night
Accommodates: 10 guests
Nestled in the heart of the Berkshires, the Private Lake House offers travelers an unparalleled escape into nature’s embrace. This serene haven, surrounded by lush landscapes and the gentle ripples of a private lake, promises a stay that’s both rejuvenating and adventurous.
The property boasts four spacious bedrooms, accommodating up to 10 guests. Whether you’re unwinding in the great room with its breathtaking water views and working fireplace or preparing a meal in the well-equipped kitchen, every moment here is a testament to relaxation. The outdoor shower adds a rustic touch, while the deck and patio provide the perfect spots to soak in the scenic beauty.
For those eager to explore, the Beartown State Forest is a mere 4-minute drive away, offering a blend of nature trails and scenic spots. The Berkshire Theatre Festival is also just a 4-minute drive, promising a dose of culture and entertainment. And for those seeking spiritual solace, the National Shrine of the Divine Mercy is a 7-minute drive away.
The Private Lake House is not just a place to stay; it’s a journey into the heart of Massachusetts’s natural beauty. It’s where memories are forged amidst the gentle rustle of the trees and where every sunrise and sunset becomes a moment to cherish.
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. Iconic Cabin in the Berkshires
Location: Sandisfield, Massachusetts
Rates from: $2,000 per night
Accommodates: 12 guests
Nestled in the heart of the Berkshires, the Iconic Cabin in the Berkshires offers travelers a blend of rustic charm and modern luxury. This spacious cabin, surrounded by nature’s beauty, promises a stay that’s both rejuvenating and memorable.
The cabin boasts six well-appointed bedrooms, accommodating up to 12 guests. With a mix of king beds, twin beds, and futons, it caters to both families and groups of friends. Every corner of this home is designed for relaxation and enjoyment – from the cozy interiors to the expansive deck and patio that offer breathtaking views of the surrounding landscapes. Whether you’re preparing a meal in the fully equipped kitchen, unwinding in the common areas, or exploring the garden, the Iconic Cabin promises a stay like no other.
For those eager to explore the surrounding area, the serene Otis Reservoir is just a 15-minute drive away. The beautiful Lake Buel and the picturesque Umpachene Falls Park are also within proximity, offering a blend of nature and adventure.
The Iconic Cabin in the Berkshires is not just a place to stay; it’s a journey into the heart of Massachusetts’s natural beauty. It’s where memories are forged amidst the gentle rustle of the trees and where every sunrise and sunset becomes a moment to cherish.
15. 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
16. 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!
17. 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
18. Oceanfront Former B&B with 5 Bedrooms
Location: Scituate, Massachusetts
Rates from: $749 per night
Accommodates: 15 guests
Nestled on the shores of Massachusetts Bay, just a stone’s throw from the soft sands of Sand Hills Beach, lies a vacation retreat that whispers the promise of coastal serenity and charm. This Oceanfront Home is not just any lodging; it’s an exquisite former inn and bed & breakfast, now inviting you to make it your temporary seaside haven.
Imagine waking up to the soothing sounds of the ocean, stepping out onto your private balcony, and being greeted by the expansive blues of the bay. Each of the five bedrooms boasts full baths and oceanfront views, ensuring that every guest experiences the tranquility of seaside living. The Lighthouse Suite, with its cozy Murphy bed and commanding views, offers a unique nautical charm that is both comforting and inspiring.
Step outside, and within a mere three-minute walk, you’ll find yourself at Sand Hills Beach, a local gem where the sands beckon for sunbathers and the waves call to the adventurous at heart. A short stroll leads to the iconic Scituate Lighthouse, a beacon of history and a perfect backdrop for those cherished vacation photos. The nearby Scituate Harbor is chock-full of shops and restaurants, offering a taste of local flavor and craftsmanship.
Amenities such as a hot tub, free WiFi, and air conditioning ensure that your stay is as comfortable as it is unforgettable. And with a location that’s just a 58-minute drive from Boston’s Logan International Airport, your dream vacation is both accessible and inviting. It’s more than a vacation rental; it’s a slice of New England paradise, waiting for you to discover.
19. 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.
20. 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
21. 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
22. 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 rental in MA, it surely doesn’t get any better than this!
The Best Airbnb Rentals in Massachusetts in 2025
Have you ever stayed in a unique Airbnb vacation rental in Massachusetts? Let me know in the comments or on Insta, 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
