As a Bostonian who escapes to the Berkshires every year, I’ve experienced some of the coziest, most scenic vacation rentals in the region. From dreamy treehouses to cozy mountain cabins and peaceful lake houses, Western MA has no shortage of amazing Airbnb stays. I’m excited to share 24 of my absolute favorites—each one offering its own unique charm to enjoy the natural beauty of the Berkshires. Whether you’re craving adventure or relaxation, this list has something for everyone!
- To discover more amazing Berkshires vacation rentals, check out these related articles: 11 Best Airbnbs in Massachusetts, 15 Unique Airbnbs in New England, 24 Unique Airbnbs in Vermont & 19 coolest Airbnbs in the US.)
The 24 Coolest Airbnbs in the Berkshires
Here are the best Berkshires Airbnbs by category, taking into account different amenities, trip types, and budgets. The subsequent sections will cover each listing in more detail.
- Top Overall: Berkshires Mountain Home
- Best Luxury Rental: Magical Country Retreat
- Most Romantic: Beautiful Mountain Cabin
- Best for Large Groups: The Taggart House
- Best Cheap Vacation Home: French-style Chalet
- Coolest Treehouse: Octagonal Treehouse
- Best Cabin: Beautiful Nature Cabin
- Best with a Pool: Luxury Berkshire Estate
- Top Winter Airbnb : Log Cabin Getaway
- Best Lake House: Cozy Retreat Lake Garfield
- Most Unique: Silo Studio Cottage Rental
Note: Some of 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. Silo Studio Cottage
Location: Tyringham, Massachusetts
Rates from: $244 per night
Accommodates: 2 guests
This treehouse in the Berkshires looks like it’s ripped from the pages of a fairytale. For that reason, it’s definitely among the most unique places to visit in the US.
Go swimming, kayaking, and hiking nearby the property, which was formerly a sculptor’s studio. With such quirky charm, Silo Studio is definitely among the most unique Airbnbs in New England.
If this one isn’t available for your selected dates, try the sister property at the end of this article for a similarly whimsical experience.
Unique features: Chiminea with firewood; 35 ft. conical ceiling; 2 acres of ponds, gardens, and woods
Cool sights nearby: Lenox | Tanglewood | Jacob’s Pillow | Stockbridge | Normal Rockwell Museum
2. Top Berkshires Vacation Rental for Budget Travelers
Location: Otis, Massachusetts
Rates from: $116 per night
Accommodates: 4 guests
Experience the Berkshires in style from this rustic apartment getaway in Otis. This modern accommodation is simple, beautiful, and within reach of many top sights in the Berkshires.
Spend your days exploring the surrounding hiking and biking trails, lakes and ponds, and local farms. Then, retreat to this cozy Berkshires vacation rental and you’ll truly feel like you’ve entered vacation mode. With so much charm and personality, this is easily one of the best places to stay in the Berkshires Massachusetts.
3. Berkshires Airbnb: Magical Country Retreat
Location: Great Barrington, Massachusetts
Rates from: $3,200 per night
Accommodates: 16 guests
It would be a crime to write about the best Airbnbs in the Berkshires and fail to mention this place. Located in Great Barrington, this magical country retreat has all the comforts of home in a surreal natural setting.
Explore 120 acres of private property as you take in the natural wonders and wildlife. Rejuvenate and find your inner peace as you relax in the pool and hot tub. It truly doesn’t get any better than this Airbnb mansion accommodation in the Berkshires. It won’t take long until you realize why this is among the best homes for rent in the Berkshires.
Unique features: 120-acre property with a main house, guest house, and barn; hot tub; pool; basketball hoop; ping pong table
Cool sights nearby: Great Barrington | Butternut Ski Area and Tubing Center | Catamount Mountain Resort | Lee | Lake Garfield | Hancock Shaker Village | Berkshire Theater Festival | Monument Mountain Reservation
4. Glass Treehouse Airbnb in the Berkshires
Location: Otis, Massachusetts
Rates from: $232 per night
Accommodates: 4 guests
Prepare to be amazed at this elegant octagonal treehouse in the Berkshires. This unique chalet offers a cozy stay and stunning panoramic views of the surrounding woodlands. This treehouse combines seamlessly pairs luxury with rustic nature vibes.
Unique features: Wood-burning fireplace; Floor-to-ceiling windows; 7 acres of forest
Cool sights nearby: Great Barrington | Tanglewood | Jacobs Pillow | Edith Wharton’s Home
5. Private Berkshire Mountain Escape
Location: West Stockbridge, Massachusetts
Rates from: $397 per night
Accommodates: 6 guests
Nestled in the serene landscapes of West Stockbridge, the Private Berkshire Mountain Escape beckons travelers with its promise of tranquility and comfort. This secluded retreat, surrounded by nature’s beauty, guarantees an experience that’s both rejuvenating and unforgettable.
The property boasts two spacious bedrooms, with the guest bedroom on the 2nd floor offering a combination of twin beds and a king bed, while the unique silo bedroom houses a twin bed. Every corner of this home whispers relaxation – from the well-appointed interiors to the outdoor spaces that beckon you to unwind and soak in the surrounding beauty.
For those keen to explore West Stockbridge, the Ebenezer II Gifts and Antiques is just a 12-minute drive away, offering a glimpse into local crafts and treasures. The Chesterwood, a historic site and former summer home of American sculptor Daniel Chester French, is a mere 14-minute drive.
The Private Berkshire Mountain Escape in West Stockbridge is not just a place to stay; it’s an invitation to immerse oneself in the heart of the Berkshires’ natural and cultural splendor. It’s where memories are forged amidst the backdrop of Massachusetts’ most cherished landscapes.
6. Beautiful Berkshire Cabin – One of the Most Unique Berkshires Vacation Rentals
Location: Sandisfield, MA
Rates from: $265 per night
Accommodates: 12 guests
Enjoy a slice of heaven at this amazing 3-acre property. Stay at this cozy cabin tucked in nature, and you’ll see why it’s one of the best Airbnbs in the Berkshires.
Unique features: Wrap around deck; Tennis court; Basketball court; Gas grill; Fireplace; Stationary bike
Cool sights nearby: Clam River | Lake Garfield | Great Barrington | Lee | Lenox | Old Sturbridge Village
7. Glamping in Hephzibah – Among the Top Berkshires Rentals for Families
Location: Chester, Massachusetts
Rates from: $133 per night
Accommodates: 4 guests
Looking for a unique glamping site in the Berkshires? The Tenor Signature provides the authentic nature getaway in New England you were looking for. During the day, relax on the Adirondack chairs and go hiking on the many trails throughout the property. At night, fall asleep to the sound of nature beneath a sky full of stars. The tent is comfortably furnished and there’s an outdoor shower and bathroom just steps away.
Unique features: Safari-style canvas tent with queen bed; Firepit; Adirondack chairs; Outdoor camp shower and toilet.
Cool sights nearby: Chester | Glendale Falls | Stockbridge | Chester-Blandford State Forest
8. Charming Unique Cottage with Stunning Mountain Views
Location: West Stockbridge, Massachusetts
Rates from: $410 per night
Accommodates: 5 guests
Tucked away in the picturesque landscapes of West Stockbridge, the Charming Unique Cottage offers travelers an oasis of calm and beauty. This delightful cottage, with its private mountain views, promises an experience that’s both serene and unforgettable.
The property features two cozy bedrooms, each furnished with a comfortable queen bed. The living room also provides additional sleeping space with a double sofa bed. Every nook and cranny of this cottage exudes warmth and relaxation, from the well-appointed interiors to the outdoor spaces that invite guests to bask in the majesty of the surrounding mountains.
For those keen to explore West Stockbridge, the Ebenezer II Gifts and Antiques is a mere 11-minute drive away, offering a treasure trove of local crafts and antiques. The Chesterwood, a historic site and former summer home of American sculptor Daniel Chester French, is just 13 minutes away by car.
The Charming Unique Cottage in West Stockbridge is not just a place to stay; it’s an invitation to immerse oneself in the heart of the Berkshires’ natural beauty and cultural richness. It’s where moments of peace and reflection are framed by the grandeur of Massachusetts’ beloved mountains.
9. The Taggart House – One of the Best Berkshires Airbnbs and VRBOs
Location: Stockbridge, Massachusetts
Rates from: $997 per night
Accommodates: 12 guests
It doesn’t get any better than this unique Airbnb in the Berkshires. Built in 1850, the Taggart House was one of the most notable estates in Massachusetts. It was restored in 2014, so the amenities are in tip top shape for a comfortable, large group stay.
Many of Normal Rockwell’s top paintings were inspired by the landscapes to the right and left of this home. Such a serene location!
Unique features: Famous historic home; indoor fireplace; each bedroom has its own bathroom; pool table; piano
Cool sights nearby: Lenox | Monument Mountain | Naumkeag | Chester Wood | Berkshire Botanic Garden | The Mount, Edith Wharton’s Home
10. Cozy Retreat on Lake Garfield – Among the Best Cabins for Rent in the Berkshires
Location: Monterey, Massachusetts
Rates from: $300 per night
Accommodates: 8 guests
Planning a getaway at a cabin rental in the Berkshires? Enjoy the best that the Berkshires has to offer at this cozy rental home on Lake Garfield. Go swimming and kayaking during the day, and watch the sunset every night over the lake and surrounding mountains. Like the rest of the Berkshires, the summer and fall leaf-peeping season in New England are the best times to visit here.
Whether you’re looking for outdoor adventure or a relaxing nature retreat, you’ll find that this home is one of the best Airbnbs in the Berkshires.
Unique features: Private deck with lounge chairs and grill; Woodstove; Master suite with loft
Cool sights nearby: Lake Garfield Beach | Tanglewood | Great Barrington | Normal Rockwell Museum |Stockbridge | Jacob’s Pillow | Bidwell House Museum
11. Beautiful Lake House for Rent in the Berkshires – A Berkshires Summer Rental Like No Other
Location: Becket, Massachusetts
Rates from: $189 per night
Accommodates: 8 guests
Looking to stay at a VRBO Berkshires or an Airbnb on the water? This house for rent in the Berkshires is the perfect summer vacation spot.
Enjoy this modern and spacious cottage in a private lake community, offering the quintessential New England retreat. Explore the 3-acre lot surrounded by trees and scenic water frontage. You won’t be far from many top outdoor activities in the Berkshires, including ski resorts, shopping outlets, and historic towns. However, once you step foot inside this cabin rental in the Berkshires, you won’t want to leave!
12. Newly Remodeled Country Castle
Location: Great Barrington, Massachusetts
Rates from: $552 per night
Accommodates: 8 guests
In the heart of Great Barrington lies a gem that redefines luxury and comfort – the Country Castle . This magnificent property, with its architectural grandeur, promises an experience that’s both regal and heartwarming.
The castle boasts three spacious bedrooms, each designed to offer the utmost comfort. The master bedroom, adorned with a king bed, is a haven of relaxation, while the guest bedroom and tower bedroom offer a queen and king bed respectively. The middle landing even houses a cozy double bed, ensuring ample space for guests.
Every corner of this castle whispers elegance – from the well-appointed interiors to the outdoor spaces that beckon you to unwind amidst nature’s embrace. For those eager to explore Great Barrington, the W.E.B. Du Bois Boyhood Homesite is a mere 12-minute walk away, offering a glimpse into the life of the iconic civil rights activist.
The Country Castle in Great Barrington is not just a place to stay; it’s an invitation to immerse oneself in the heart of Massachusetts’ cultural and natural beauty. It’s where moments of grandeur and tranquility come together, creating memories that last a lifetime.
13. Mountain and Lake View House for Rent – The Berkshires Vacation Rentals Like No Other
Location: Great Barrington, Massachusetts
Rates from: $595 per night
Accommodates: 9 guests
Nothing says the Berkshires like beautiful lake and mountain views from a Berkshires cabin rental. Relax and let all of life’s worries subside inside this unique mountaintop home. Go skiing, swimming, and hiking with a front-row seat of nature, and you’ll quickly realize why this is one of the most unique Airbnbs in the Berkshires.
This part of the Berkshires is a picture-perfect stop on a New England road trip itinerary. While it’s a great home base anytime of year, it’s one of the most popular Berkshires summer rentals.
Unique features: Hot tub; Fire pit; Grill; Hammocks; Screened sunroom
Cool sights nearby: Great Barrington | Stockbridge | Lenox
14. Lake View Cabin for Rent in the Berkshires
Location: Tolland, Massachusetts
Rates from: $220 per night
Accommodates: 8 guests
Planning on where to stay in the Berkshires of MA? Bring the whole family along to enjoy one of the coolest cabin rentals in the Berkshires. This vacation home overlooks a lake and gorgeous vegetation as far as the eye can see.
Spend your days exploring all the outdoor adventures that Southwestern Massachusetts has to offer. Catch sunrise with a cup of coffee in-hand on Cranberry Pond. Take advantage of the gas grill, Adirondack chairs, bath house, tennis courts, basketball hoops, and other unique amenities. It won’t be long until you realize why this is among the top Berkshires vacation rentals!
15. Wooden Cottage in Berkshires Hills – A VRBO Berkshires with All the Comforts of Home
Location: Monterey, Massachusetts
Rates from: $160 per night
Accommodates: 4 guests
Have you ever stayed in a wooden cottage before? This charming home in the Berkshires is decked out with rustic fixtures, beautiful gardens, and all the essentials to make your visit to the Berkshires a memorable one.
Enjoy the glass porch and lush gardens. While you can’t go wrong here any season, it’s especially considered one of the best Berkshires summer rentals in MA.
Unique features: Glass-enclosed sun room; Perennial gardens; Gazebo
Cool sights nearby: Tanglewood | Jacob’s Pillow | Shakespeare & Co. | Berkshire Theatre Festival | Great Barrington
16. Cozy French Country Chalet – Top Budget-friendly Airbnb in the Berkshires
Location: Monterey, Massachusetts
Rates from: $150 per night
Accommodates: 6 guests
Bring the whole family along to enjoy this cozy home in the heart of Western Massachusetts. This unique vacation rental in the Berkshires is reminiscent of the chalets that you’ll find in the Austrian, French, and Swiss Alps.
Unique features: Two-floor chalet; Screened-in porch; Grill; Family games, books, and movies
Cool sights nearby: Tanglewood | Jacob’s Pillow | Shakespeare & Co. | Berkshire Theatre Festival | Great Barrington
17. Private Island – Directly on Largest Fresh Water Reservoir in Massachusetts
Location: Otis, Massachusetts
Rates from: $449 per night
Accommodates: 6 guests
Imagine waking up on your very own private island, surrounded by the pristine waters of Massachusetts’ largest freshwater reservoir. The Private Island in Otis offers just that – an unparalleled experience of tranquility and natural beauty.
This unique property boasts two cozy bedrooms, with the first bedroom housing a comfortable queen bed and the second featuring a twin bunk bed. Additional sleeping space is provided in the common area with a plush queen bed. Every space in this island retreat is designed to maximize the breathtaking views of the reservoir, ensuring guests are always in touch with nature.
For those looking to explore the surroundings, the Otis Reservoir is just a 5-minute walk away, perfect for water activities and relaxation. A short 5-minute drive will take you to the County Beach, offering sandy shores and clear waters. The Tolland State Forest, a haven for hiking and outdoor adventures, is only an 11-minute drive from the property.
The Private Island in Otis is not just an accommodation; it’s a once-in-a-lifetime experience. It’s where the serenity of nature meets the luxury of modern amenities, creating an unforgettable escape in the heart of Massachusetts.
18. The Redway House – One of the Most Unique Berkshires Vacation Rentals for Summer Stays
Location: Stockbridge, Massachusetts
Rates from: $414 per night
Accommodates: 6 guests
Experience the Berkshires at its finest at this tranquil vacation rental in Stockbridge. The Redway House is set on 114 acres of beautiful forested property with sweeping views of the surrounding forest and valley. The property is also home to abundant wildlife, including whitetail deer, beavers, owls, and turkeys.
Unique features: Cozy fireplace; Spacious private deck; In-unit laundry machines; 114 acres of forest; Gas grill
Cool sights nearby: Stockbridge | Hancock Shaker Village | Berkshire Botanical Center | North Adams + Mass MoCA (50 mins)
19. Berkshire Mountains Cabin – One of the Finest Cabin Rentals in the Berkshires MA
Location: Monterey, Massachusetts
Rates from: $334 per night
Accommodates: 9 guests
Enjoy nature at its finest at this unique log cabin in Berkshire County. Relax in the hot tub while soaking in the beautiful wilderness, or go hiking, kayaking, and swimming nearby. With so much charm and top amenities, it’s no wonder this is among the top cabin rentals in the Berkshires.
There’s plenty of fun outdoor activities to justify spending at least a few nights, so bring your extended family or friends along to enjoy all that the Berkshires has to offer.
Unique features: Hot tub; Fireplaces; Gas grill; Screened porch
Cool sights nearby: Beartown State Forest | Lake Garfield | Tanglewood | Lenox | Great Barrington
20. Log Mountain Retreat is Among the Coolest Airbnbs in the Berkshires
Location: Monterey, Massachusetts
Rates from: $671 per night
Accommodates: 15 guests
Looking for a unique vacation rental in the Berkshires for large groups of families or friends? Then this is it.
This cozy and upscale log cabin is centrally located within 30 minutes of most attractions in the Berkshires. It comes with all the amenities you’d expect in such a large mountain lodge, ideal for large groups. It’s also among the few Berkshires vacation rentals that’s pet friendly! If you’re looking to stay at one of the coolest Berkshires summer rentals, this house for rent has got you covered.
Unique features: Charcoal BBQ grill; Wood-burning stove; 5 bedrooms; 4.5 baths
Cool sights nearby: Butternut Ski Mountain | Windy Hill Farm | Monument Mountain | Tanglewood | Jacob’s Pillow | Norman Rockwell Museum | Lenox | Great Barrington | Lee
21. The Playhouse: Berkshires Modern Luxury Meets History
Location: Lee, Massachusetts
Rates from: $1,207 per night
Accommodates: 20 guests
Nestled in the heart of the Berkshires, The Playhouse offers a blend of modern luxury and rich history spread across a sprawling 7,000 square feet. This exceptional property, with its six well-appointed bedrooms, promises a stay that’s both grand and memorable.
The interiors exude sophistication, from the spacious living areas to the state-of-the-art kitchen. Whether you’re preparing a gourmet meal, unwinding in one of the five pristine bathrooms, or simply soaking in the ambiance of this historic gem, The Playhouse ensures a delightful stay.
For those eager to explore the Berkshires, The Mount is just a 3-minute drive away, offering a glimpse into the life of famed novelist Edith Wharton. For music enthusiasts, the renowned Tanglewood Music Center is an 8-minute drive, promising unforgettable performances in a picturesque setting.
The Playhouse in Lee, MA, is not just a place to stay; it’s an invitation to immerse oneself in the heart of the Berkshires’ cultural and natural splendor. It’s where memories are forged amidst the backdrop of Massachusetts’ most cherished landscapes.
22. Quintessential House Rental in the Berkshires of Massachusetts – One of the Best Berkshires Vacation Rentals
Location: Lenox, Massachusetts
Rates from: $332 per night
Accommodates: 6 guests
Stay at this gorgeous house for rent in the Berkshires, and you’ll be in for a treat. This modern and elegant accommodation is just steps from downtown Lenox, but exudes a feeling of calm and tranquility.
Take advantage of the mid-century decor and vintage designs throughout the property. Relax in the sun from the large landscaped backyard with spacious deck. Curl up by the fireplace and roast some s’mores. If you’re looking for a top Airbnb or VRBO in the Berkshires, this home has got you covered.
23. Spacious Berkshire Home – A Unique House to Rent in the Berkshires during the Summer
Location: Sandisfield, Massachusetts
Rates from: $320 per night
Accommodates: 8 guests
Looking for the best place to stay in the Berkshires? Lose yourself in this amazing Airbnb overlooking 30 acres of unspoiled nature.
This spacious Berkshire home is equipped with all the Shop ‘til you drop in classic New England towns like Great Barrington, canoeing in pristine lakes and ponds, and hiking through the many trails nearby. With so much charm and personality, this house to rent in the Berkshires is easily among the best vacation rentals in Western Massachusetts.
Unique features: Fireplaces in rooms; 28-foot ceilings; 1200 sq. ft. deck overlooking nature
Cool sights nearby: Great Barrington | Hancock Shaker Village | Berkshire Theater Festival | Many lakes and hiking trails
24. Grand Silo Tower Suite – Unique Berkshires Airbnb
Location: Tyringham, Massachusetts
Rates from: $259 per night
Accommodates: 4 guests
If the unique accommodation above doesn’t have any dates available, try this one. The Grand Silo Tower Suite is another property on the same estate as the Silo Studio Cottage. It’s a bit larger yet offers the same magical treehouse experience. The pictures say it all.
The Grand Silo Tower Suite is a part of the Santarella Estate, one of the best hidden gems in the US.
Unique features: Winding staircase; third story loft; 2 acres of ponds, gardens, and woods
Cool sights nearby: Lenox | Tanglewood | Jacob’s Pillow | Stockbridge | Normal Rockwell Museum
Top Berkshires Airbnb: Coolest Rentals in Berkshire County MA
Have you ever stayed in a unique Airbnb or vacation rental in the Berkshires? Let me know in the comments or on Insta, as I’m always looking to add to this list of the most unique Airbnbs in the Berkshires!
Looking for more cool New England adventures? Check out these dreamy destinations:
– Coolest Airbnb Rentals in Massachusetts
– Unique Airbnbs in the White Mountains
– Best Airbnbs in Rhode Island
For further reading, check out my other New England and East Coast articles:
