The widest selection of unusual accommodations in The Berkshires

A cabin, a lighthouse, a glamping, your extraordinary stay awaits you

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The Berkshires unique stays
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344 Unique places to stay in The Berkshires

Best The Berkshires unusual places with a balcony

Scribe`s Stable | A/c  Screened In Porch  Sleeps 6 - The Berkshires
10 4 reviews

Scribe`s Stable | A/c Screened In Porch Sleeps 6

manor house, Monterey
This renovated barn, a short drive (less than 2km) from Monterey Town Beach in Monterey, Massachusetts, provides easy access to Tanglewood, Butternut Ski Area, and the Appalachian Trail.
The 167 square metre property features two bedrooms, one bathroom, sleeping up to six guests, and includes a kitchen with microwave, air conditioning, a terrace, garden, parking, and Wi-Fi.
Cabin W/ 3 Acres, Tennis Courts: By 4 Ski Mtns - The Berkshires
9.6 135 reviews

Cabin W/ 3 Acres, Tennis Courts: By 4 Ski Mtns

cabin, Sandisfield
This charming four-bedroom cottage is situated in Sandisfield, Massachusetts, just 26 kilometres from the Cranwell Spa & Golf Club, 27 kilometres from the Norman Rockwell Museum, and 29 kilometres from Tanglewood, offering easy access to popular attractions. The property has received excellent ratings for its location, cleanliness, and overall experience.
This 184 square metre dwelling comfortably accommodates up to 10 guests and boasts a fully equipped kitchen, a spacious living area, and a private garden. Guests can enjoy a range of amenities including a tennis court, a spa, and free Wi-Fi, ensuring a relaxing and enjoyable stay.

Discover Family-Friendly Unique Stays in The Berkshires

Reconnect with nature during family holidays in The Berkshires staying in accommodation everyone will talk about.

Little Longbow Lakefront Chalet - The Berkshires
9.8 35 reviews

Little Longbow Lakefront Chalet

chalet, Becket
This Becket lakeside lodge is situated within 3.2km of Pyramid Lake, Jacob's Pillow Dance Festival, and 3km from October Mountain State Forest, offering easy access to swimming, boating, hiking and world-class dance performances.
Sleeping five guests, this two-bedroom, two-bathroom property boasts a private garden, terrace, spa, air conditioning, Wi-Fi, and barbecue facilities, perfect for a family getaway.
Berkshires Chalet Natural Setting Deck & Fire Pit! - The Berkshires
9.8 27 reviews

Berkshires Chalet Natural Setting Deck & Fire Pit!

chalet, Otis
This charming chalet is located in the Berkshires, a short drive from Tanglewood and Jacob's Pillow, and a mile from Otis Ridge ski area, offering a peaceful retreat in a beautiful setting. This property has consistently received excellent ratings for its cleanliness, location and overall experience.
The chalet has four bedrooms, three bathrooms, and can comfortably accommodate up to eight guests. It features a spacious living area with a wood-burning stove, a well-equipped kitchen, a large private yard with a fire pit and a screened-in porch, and a variety of amenities for a comfortable stay.
Berkshire Treehouse Retreat - The Berkshires
9.8 178 reviews

Berkshire Treehouse Retreat

cabin, New Marlborough
This double treehouse is located in New Marlborough, just 8km from the town of Great Barrington and a 20-minute drive to its centre. The property has received excellent ratings for location, cleanliness, and overall user experience.
The treehouse has two levels, offering separate sleeping and working spaces, and can accommodate up to five guests. It boasts a unique design, incorporating a live tree running through the interior, and includes a kitchenette, gas grill, solo stove, and outdoor dish station for a comfortable glamping experience.
Berkshires Cabin 2 Mi To Appalachian Trail! - The Berkshires
9.6 45 reviews

Berkshires Cabin 2 Mi To Appalachian Trail!

cabin, Otis
The Berkshires Cabin 2 Mi to Appalachian Trail! is located in Otis, just 3.2km from the Appalachian Trail and within a short drive of attractions such as Cranwell Spa & Golf Club, Tanglewood, and Tanglewood Musical Center. The property has excellent user, location, and cleanliness ratings.
This 3-bedroom holiday home is 111 square metres and can accommodate up to 7 guests. The cabin has a fully equipped kitchen, a garden, a spa, free Wi-Fi, a flat-screen TV, and parking.

Frequently asked questions about unique stays in The Berkshires

  • What attractions is Monts Berkshire famous for?

    The Berkshires is known for its stunning natural beauty, with the Appalachian Mountains running through the region. You'll find plenty of hiking trails, lakes, and forests to explore. It's also known for its vibrant arts and culture scene, with several world-renowned museums, theaters, and music venues. Tanglewood, the summer home of the Boston Symphony Orchestra, is a must-visit for music lovers.
  • What clothing or gear is recommended for the climate in Monts Berkshire?

    The Berkshires has four distinct seasons, so pack accordingly. In the summer, it's warm and humid, so light clothing is best. In the autumn, it's crisp and cool, so you'll want to pack layers. Winter can be very cold and snowy, so pack warm clothing, a hat, gloves, and a scarf. And don't forget your hiking boots if you plan on exploring the many trails.
  • What are the best ways to travel to Monts Berkshire eco-consciously?

    The Berkshires is easily accessible by train from New York City. The Amtrak train line runs directly to Pittsfield, and from there, you can take a bus or rent a car to get around. Another option is to drive an electric car, as there are several charging stations in the region. If you're flying, consider offsetting your carbon emissions.
  • Which neigbourhood offers the best unique stays in Monts Berkshire?

    Stockbridge is known for its charming inns and bed and breakfasts, many of which are housed in historic buildings. You'll also find several unique accommodations in Lenox, including the historic Cranwell Resort and Spa and the modern The Orchards. For a more rustic experience, head to the Berkshires' western towns, where you can find cabins and glamping sites.
  • What should you know about unique stays in Monts Berkshire before booking?

    Before booking a unique stay, it's important to consider your needs and preferences. Some unique accommodations may be more remote or have limited amenities. It's also important to check the availability and pricing, as these can vary depending on the time of year. Finally, be sure to read reviews from other guests before booking.

Popular destinations

Best Unusual Places to Stay with a Jacuzzi in The Berkshires

Soak in the scenery from a private hot tub at these one-of-a-kind properties-the ultimate way to enjoy a unique stay in The Berkshires.

Quiet Comfortable Cabin 5 Min. Walk To Swimming And Boating - The Berkshires
9.6 259 reviews

Quiet Comfortable Cabin 5 Min. Walk To Swimming And Boating

cabin, Becket
This charming cabin is located in Sherwood Forest, just outside of Becket, within 10km of Pyramid Lake, Iroquis Waterfront, Jacob's Pillow, October Mountain State Forest, and Becket Land Trust Historic Quarry. It enjoys a peaceful setting, offering a tranquil escape from the hustle and bustle of town. This cabin has been rated excellent by previous guests.
The cabin spans 59 square meters and comfortably sleeps up to four guests in its two bedrooms. It boasts a range of amenities, including a fully equipped kitchen, a garden, a terrace, and a fireplace, allowing guests to enjoy both indoor and outdoor relaxation.

Best The Berkshires unusual places with a sauna

Misty Pines Cabin | Wood Stove  Sauna - The Berkshires
10 1 review

Misty Pines Cabin | Wood Stove Sauna

cabin, Monterey
This log lodge, situated amongst the tall pines of Monterey, Massachusetts, offers a secluded woodland experience and is located a mere few minutes' drive from Beartown State Forest, Lake Garfield, and the Bidwell House Museum.
This pet-friendly lodge accommodates up to eight guests across three bedrooms, featuring a fully equipped kitchen with a fridge and dishwasher, a garden, parking, and an outdoor wood-fired sauna for relaxation.
Misty Pines Cabin | Wood Stove  Sauna - The Berkshires
10 26 reviews

Misty Pines Cabin | Wood Stove Sauna

cabin, Monterey
This Monterey lodge is located among tall pines, a short distance from Beartown State Forest, Lake Garfield, Steadman Pond, Greene Park, and the Bidwell House Museum.
This three-bedroom, three-bathroom holiday home accommodates eight guests and features a fully equipped kitchen, a wood-fired sauna, a garden, and parking, with a rustic log cabin feel and an outdoor wood-fired sauna for relaxation.

Browse 5-Star Unusual Places to Stay in The Berkshires

Escape to a luxury unique stay in the hills of The Berkshires, where unconventional design meets high-end comfort for a memorable retreat.

Scribe's Stable | A/c  Screened Porch  Sleeps 6 - The Berkshires
9.9 67 reviews

Scribe's Stable | A/c Screened Porch Sleeps 6

farm, Monterey

Compare Unusual Places to Stay with a Swimming Pool in The Berkshires

Each mountain unique stay in The Berkshires with a pool provides a revitalising post-hike dip.

Cozy Cabin In The Berkshires - The Berkshires
10 21 reviews

Cozy Cabin In The Berkshires

cabin, Sandisfield
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