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

Cabin W/ 3 Acres, Tennis Courts: By 4 Ski Mtns - The Berkshires
9.7 132 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.

Cozy Cabin In The Berkshires - The Berkshires
10 20 reviews

Cozy Cabin In The Berkshires

cabin, Sandisfield
This charming two-bedroom cabin is situated in the beautiful Berkshires, just a short drive from Sandisfield, with Butternut ski resort 40km away and Jiminy Peak 80km away. The cabin has received excellent user, location, and cleanliness ratings, making it a top choice for travellers.
The property has two bathrooms and can comfortably accommodate up to eight guests, offering plenty of space for families or groups of friends. The cabin features a fully equipped kitchen, a screened-in deck, a loft with four twin beds, a basement with a pool table and dart board, a fire pit, and a grill, ensuring a comfortable and enjoyable stay for all.
Iconic Lodge In The Berkshires - The Berkshires
9.7 63 reviews

Iconic Lodge In The Berkshires

cabin, Sandisfield
This four-bedroom lodge is situated in the Berkshires, a scenic region of Western Massachusetts, about 48 kilometres from Stockbridge, Great Barrington, and Otis Reservoir. The property has received excellent ratings for location, cleanliness, and user experience.
The lodge is spacious and can accommodate up to 12 guests. It offers a range of amenities, including an indoor pool, a billiards lounge, a large dining room, a well-equipped kitchen, and a private garden.
Berkshire Treehouse Retreat - The Berkshires
9.8 158 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.
Cozy Monterey Family Chalet, Minutes From Lake & 10 Minutes From Butternut! - The Berkshires
10 221 reviews

Cozy Monterey Family Chalet, Minutes From Lake & 10 Minutes From Butternut!

chalet, Monterey
This charming French Country chalet is situated in the Berkshires, just 3 kilometres from Monterey town centre, 4 kilometres from Lake Garfield, and 10 kilometres from Butternut ski resort. The chalet has consistently received excellent ratings for its location, cleanliness, and overall experience.
The chalet spans 125 square metres and comfortably accommodates up to 6 guests in its two bedrooms and one bathroom. It offers a range of amenities, including a fully equipped kitchen, a screened-in porch, a deck with a grill, a spa, a fitness centre, and high-speed internet, making it ideal for families or groups seeking a relaxing getaway in the Berkshires.

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.

Fantastic Cottage In The Berkshire Mountains - The Berkshires
9.9 305 reviews

Fantastic Cottage In The Berkshire Mountains

cabin, Monterey
This four-bedroom lodge is located just a short drive from the Appalachian Trail, Beartown State Forest, and Lake Garfield, offering a peaceful retreat in the heart of the Berkshire Mountains. It has received excellent ratings for its location, cleanliness, and overall experience.
The 232 square metre property features a fully equipped kitchen, two fireplaces, a hot tub, and a screened porch. Guests can enjoy hiking trails, kayaking, swimming, and access to a fire pit, as well as a selection of DVDs, games, and books.

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 19 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.

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

Misty Pines Cabin | Wood Stove Sauna

cabin, 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.

Iconic Lodge In The Berkshires - The Berkshires
9.7 63 reviews

Iconic Lodge In The Berkshires

cabin, Sandisfield
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