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This Pittsfield apartment is located near Tanglewood Music Center, Colonial Theater, Herman Melville's Arrowhead, and Hancock Shaker Village.
This one-bedroom, one-bathroom unit accommodates up to four guests and features a king bed, a sofa bed, air conditioning, and internet.

This Jiminy Peak one-bedroom condo offers ski-in/ski-out access at the base of the ski resort, providing unparalleled convenience for winter sports enthusiasts. With very good user and cleanliness ratings, this condo is an excellent choice for travelers seeking a comfortable and well-equipped accommodation.
The condo features a fully equipped kitchen, a master bedroom with a king-size bed, and a living room with a queen-size sleep sofa, accommodating up to five guests. Amenities include air conditioning, a swimming pool, a Jacuzzi, a fitness center, and parking. The condo also offers a ski locker on the main floor for secure storage of ski equipment.

This 1847 New England farmhouse rental in downtown Pittsfield offers convenient access to theaters, restaurants, and is a short drive from Tanglewood, Bousquet Ski Area, and Hancock Shaker Village.
The four-bedroom, one-bathroom house sleeps seven guests and features a kitchen with a fridge, freezer, and microwave, keyless entry, on-site host assistance, a spacious sunroom, wraparound porch, backyard deck, and a fire pit.

This five-bedroom, three-bathroom house in Jiminy Peak Mountain Resort's exclusive Black Diamond section in Hancock, Massachusetts offers ski-in/ski-out access to Grouse Run.
The 2,600+ square-foot home boasts a chef's kitchen, game room, fireplace, private balcony with gas grill, and sleeps up to 10 guests (4 adults and 6 children), with access to the Country Inn's amenities including pools, hot tubs, and tennis courts.

This expansive country estate is located in Stephentown, approximately 5 miles from Jiminy Peak Mountain Resort and close to attractions like Tanglewood and the Clark Art Institute.
This 13-bedroom, 12-bathroom mansion accommodates up to 40 guests with a chef's kitchen, game room, heated pool, year-round hot tub, and sand volleyball court, offering 6500 square feet of living space.

This ski-in/ski-out condo is located at Jiminy Peak Resort in Hancock, Massachusetts, offering easy access to the Berkshires towns of Williamstown, North Adams, Lee, Lenox, and Pittsfield.
This spacious corner unit boasts two full bathrooms, sleeps four guests, and features a fully equipped kitchen, plus access to resort amenities including a heated pool, hot tub, fitness center, and sauna.

This 6-bedroom, 4-bathroom condo in Hancock is located a 5-minute walk from Jiminy Peak Mountain Resort and an 8-minute drive from Alpine Super Slide.
This pet-friendly accommodation offers Wi-Fi, a full kitchen with a microwave and dishwasher, air conditioning, a swimming pool, jacuzzi, garden, and on-site parking for up to 12 guests.

This Pittsfield vacation home offers a central location, within a 10-minute walk of the Berkshire Athenaeum, Colonial Theatre, and Berkshire Museum, and less than a mile from the Barrington Stage Company and the Housatonic River.
This four-bedroom, two-bathroom house sleeps seven and features a fully equipped kitchen with a refrigerator, microwave, dishwasher, and a coffee/tea maker, plus a Smart TV, in-unit laundry, and on-site parking.

This ski-in/ski-out condo at Jiminy Peak Resort in Hancock, Massachusetts offers direct access to 45 slopes.
The spacious one-bedroom unit features two bathrooms, a fully equipped kitchen with microwave and dishwasher, and accommodates up to four guests, boasting resort amenities including a pool, jacuzzi, and fitness center.

This 6,000-square-foot Williamstown estate, 18 miles from the Bennington Battle Monument and 28 miles from Cranwell Spa & Golf Club and Tanglewood, offers a spacious retreat for large groups.
The seven-bedroom, five-bathroom property boasts a fully equipped kitchen, fitness center, garden, and accommodates up to 16 guests, providing ample space and amenities for a comfortable stay.

Huttopia Berkshires luxury tents are located in Hancock, Massachusetts, approximately 23 miles from Cranwell Spa & Golf Club and 26 miles from Tanglewood.
The Huttopia Berkshires offer features a one-bedroom, one-bathroom unit with a fully equipped kitchenette, private terrace, access to an outdoor pool, and on-site restaurant, plus free parking and pet-friendly accommodations.