
Hawthorne Barn
farm, Stockbridge
This renovated barn guesthouse is located less than a mile from Tanglewood and a short walk to Lenox, with Stockbridge Bowl nearby, offering 6 guests a secluded stay with forest views.
This standalone guest house features a full kitchen with a fridge, freezer, and dishwasher, air conditioning, a garden, parking, and is equipped with internet, providing access to summer herb and vegetable gardens and proximity to Jiminy Peak and Butternut ski resorts for winter activities.
This standalone guest house features a full kitchen with a fridge, freezer, and dishwasher, air conditioning, a garden, parking, and is equipped with internet, providing access to summer herb and vegetable gardens and proximity to Jiminy Peak and Butternut ski resorts for winter activities.

Lakeside Berkshires Cabin W/ Private Dock & Views
cabin, Lee
This lakeside cabin in Lee offers a private dock and lake views, located 6.9 miles from Cranwell Spa & Golf Club and 9.5 miles from the Tanglewood Musical Center.
This 1500 square foot vacation home accommodates up to 7 guests with 2 bedrooms and 2 bathrooms, featuring air conditioning, internet, a full kitchen, and a terrace.
This 1500 square foot vacation home accommodates up to 7 guests with 2 bedrooms and 2 bathrooms, featuring air conditioning, internet, a full kitchen, and a terrace.

Modern Chalet Near Tanglewood & Downtown Lenox
chalet, Lenox
This modern A-frame house is located in Lenox, within walking distance of Tanglewood, Kennedy Park, and Kripalu, offering easy access to cultural events, outdoor activities, and wellness retreats. The property has received excellent ratings for user experience, location, and cleanliness.
The house has a split-level design that can accommodate up to 6 guests and features a dedicated lower floor for children and elderly members, while the upper mezzanine provides privacy for adults. This family-friendly retreat offers a fully equipped kitchen, laundry facilities, a private garden, ample parking, and a basement with a ping pong table for entertainment.
The house has a split-level design that can accommodate up to 6 guests and features a dedicated lower floor for children and elderly members, while the upper mezzanine provides privacy for adults. This family-friendly retreat offers a fully equipped kitchen, laundry facilities, a private garden, ample parking, and a basement with a ping pong table for entertainment.

Taggart River House: Modern Luxury Meets Nature: Stunning River Views, Sleeps 10
manor house, Stockbridge
This Stockbridge farm stay, a luxurious guest house near the Housatonic River, is two blocks from downtown Stockbridge and the Red Lion Inn, and within two miles of Tanglewood, the Norman Rockwell Museum, Chesterwood, and the Berkshire Botanical Garden.
The 4,500-square-foot property boasts five bedrooms, five and a half bathrooms, and accommodates up to ten guests, featuring a spacious open floor plan, modern amenities, and a terrace overlooking the river.
The 4,500-square-foot property boasts five bedrooms, five and a half bathrooms, and accommodates up to ten guests, featuring a spacious open floor plan, modern amenities, and a terrace overlooking the river.

Enchanted Tiny Tower Nestled In The Berkshires
cabin, Tyringham
The Enchanted Tiny Tower is located on the Santarella Estate in Tyringham, MA, just a short drive from the Berkshires' popular attractions like the Clark Art Institute and Mount Greylock. This unique accommodation has received excellent ratings for its location, cleanliness, and overall experience.
This charming tower features a cozy interior with a fully equipped kitchenette, a dining area, a comfortable sofa, and a canopied queen bed, perfect for a couple's getaway. Enjoy the serene sounds of the babbling brook, explore the spacious garden and pond, and relax by the outdoor fireplace.
This charming tower features a cozy interior with a fully equipped kitchenette, a dining area, a comfortable sofa, and a canopied queen bed, perfect for a couple's getaway. Enjoy the serene sounds of the babbling brook, explore the spacious garden and pond, and relax by the outdoor fireplace.

Gingerbread House Tower In The Berkshire Hills
cabin, Tyringham
This Tyringham, Massachusetts cabin, located on the Santarella Estate in the Berkshires, offers easy access to nearby Berkshire towns and walking trails.
The newly renovated two-bedroom, one-bathroom cottage sleeps four, boasting a loft with a tower bedchamber, an open-concept living space, a well-equipped kitchenette with a Ninja Foodi XL and induction cooktop, and a large bathroom with a double vanity; the four-acre estate grounds feature gardens, a lily pond, stone bridges, a brook, and a chimnea.
The newly renovated two-bedroom, one-bathroom cottage sleeps four, boasting a loft with a tower bedchamber, an open-concept living space, a well-equipped kitchenette with a Ninja Foodi XL and induction cooktop, and a large bathroom with a double vanity; the four-acre estate grounds feature gardens, a lily pond, stone bridges, a brook, and a chimnea.

Timpani Corners | Private Pond Ac
cabin, Lenox
This pet-friendly cabin offers a unique waterfront setting on a private quarry pond beside a brook in Lenox, located 9 miles from Tanglewood and The Mount, and 6 miles from Bousquet Mountain Ski Area.
This 820 sq ft retreat accommodates up to 6 guests with 3 bedrooms, a full kitchen, air conditioning, and Wi-Fi, situated on a spacious yard with an outdoor grill, providing easy access to local attractions and a full-time local support team.
This 820 sq ft retreat accommodates up to 6 guests with 3 bedrooms, a full kitchen, air conditioning, and Wi-Fi, situated on a spacious yard with an outdoor grill, providing easy access to local attractions and a full-time local support team.

Lakeside Berkshires Cabin W/ Private Dock & Views
cabin, Lee
This two-bedroom, two-bathroom lakeside cottage in Lee offers direct access to Goose Pond, featuring a provided kayak for water exploration and a waterfront deck for relaxing views.
This pet-friendly retreat accommodates up to four guests with amenities including internet, air conditioning, a full kitchen with a fridge and microwave oven, a big-screen TV, board games, a gas grill, and an outdoor shower, all situated within the scenic Berkshires.
This pet-friendly retreat accommodates up to four guests with amenities including internet, air conditioning, a full kitchen with a fridge and microwave oven, a big-screen TV, board games, a gas grill, and an outdoor shower, all situated within the scenic Berkshires.
