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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380 Unique places to stay in The Berkshires

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 25 reviews
The Berkshires
31/08 – 03/09
£518/nighttotal: £1554 (3 )

Little Longbow Lakefront Chalet

2 2
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.
Cozy Cabin In The Berkshires - The Berkshires
10 17 reviews
The Berkshires
22/09 – 25/09
£236/nighttotal: £708 (3 )

Cozy Cabin In The Berkshires

1 2
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.
Simple, Rustic, Cozy Get Away - The Berkshires
9.4 32 reviews
The Berkshires
23/10 – 25/10
£171/nighttotal: £342 (2 )

Simple, Rustic, Cozy Get Away

1 2
cabin , Otis
This charming cabin in Otis is situated just one lot away from the lake, offering a shared dock and access to the water. The peaceful surroundings provide a tranquil escape from the everyday hustle and bustle.
The two-bedroom cabin can comfortably accommodate up to four guests. Amenities include a fully equipped kitchen, air conditioning, and a screened porch, perfect for enjoying the beautiful sunsets.
Family Lake Retreat | Sauna, Deck & Games - The Berkshires
9.8 92 reviews
The Berkshires
14/08 – 17/08
£741/nighttotal: £2223 (3 )

Family Lake Retreat | Sauna, Deck & Games

5 2
chalet , Otis
This chalet is located just 20km from Tanglewood, nestled in the tranquil forest setting of Otis, Berkshire County, Massachusetts. The property has received excellent ratings for its cleanliness, location, and user experience.
The chalet has five bedrooms, a cosy loft, and can accommodate up to ten guests. It offers a range of amenities, including a fully equipped kitchen, a home office with high-speed WiFi, a Tesla-compatible charger, and a unique Nordic experience with an exterior barrel sauna.

Best The Berkshires unusual places with a balcony

Cabin With 3 Acres, Tennis Courts By 4 Ski Mtns - The Berkshires
9.7 126 reviews
The Berkshires
31/08 – 03/09
£264/nighttotal: £792 (3 )

Cabin With 3 Acres, Tennis Courts By 4 Ski Mtns

4 2
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.
Scribe`s Stable | A/c  Screened In Porch  Sleeps 6 - The Berkshires
10 4 reviews
The Berkshires
16/07 – 19/07
£376/nighttotal: £1128 (3 )

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

2 3
farm , 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.

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.

Destinations nearby

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.

Butterfly Bungalow - The Berkshires
10 5 reviews
The Berkshires
22/09 – 25/09
£192/nighttotal: £576 (3 )

Butterfly Bungalow

1 2
cabin , Otis
Butterfly Bungalow, a woodland retreat in Otis, Massachusetts, offers a secluded escape in the Berkshires, easily accessible from local attractions.
This self-catering cottage, sleeping four adults in two bedrooms and one bathroom, features a full kitchen, laundry facilities, a private outdoor shower, fire pit, and covered porch with additional outdoor seating; solar-powered fairy lights enhance the evening atmosphere.

Best The Berkshires unusual places with a sauna

Bedroom Forest View I Sauna I Fire-pit I Trails - The Berkshires
9.9 166 reviews
The Berkshires
23/10 – 25/10
£265/nighttotal: £530 (2 )

Bedroom Forest View I Sauna I Fire-pit I Trails

1 2
cabin , New Marlborough
This one-bedroom cabin in New Marlborough is situated beside the Umpachene River, a short distance from the Appalachian Trail and the town centre.
The cabin is equipped with a well-equipped kitchen, a private sauna, and an outdoor shower, comfortably accommodating up to four guests.
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