House holiday rentals in Boys & Girls Club of the Berkshires Ice Rink

Bright Stockbridge country home, near everything!

Berkshires charm in this fully renovated 1800's post and beam farmhouse set on 5 park-like acres. Features open plan living/dining/kitchen with gas cooktop and gas 3 sided fireplace, lovely sun room, master suite downstairs and 2 br, bath and sitting area upstairs. Spacious deck overlooking the expansive property Conveniently located between the charming towns of Stockbridge, Lenox & Great Barrington. We are surrounded by 4 ski areas, the closest is 10 minutes away! Many dining options too.

Berkshire 4 season home

The house is located in the heart of the Berkshires. It's less than 10 miles from Tanglewood, Kripalu, Jacob's pillow Dance, Monument Mountain, Beartown state forest, Norman Rockwell Museum, Shakespeare & Co., Ski Butternut, Lee Prime outlets. Located 1.5 miles from the turnpike exit for easy travel, 3 miles from Laurel lake, walking distance to a public golf course and downtown Lee where you will find great restaurants. There is Cable internet that is fast and reliable if you have to work.

Cantabile life in the Berkshires

Relax with your family and friends after a day of skiing, hiking or a night of Tanglewood concert in this newly renovated home at the center of the Berkshires. Located in a quiet and friendly neighborhood, our home is 5min to Pontoosuc Lake and Lake Onota, 10min to Bousquet, 15min to Mt Greylock, 20min to Jiminy Peak and Tanglewood. Multiple grocery stores and shopping centers near by. Child/baby friendly, we have books, games, PingPong, foosball and a grand piano. Musicians are welcome!

Berkshire Mountain retreat with Urban eco-luxuries

600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, hear the great musicians at Tanglewood, take in a play at Shakespeare & Co, or just relaxing our wood-fired hot tub- we hope you enjoy your stay and will visit us again.

Cozy lakehouse

Relax with family or friends at this sweet cottage on Center Lake in the Berkshires. This lakeside cottage is charming and rustic. Enjoy a beautiful day on the lake swimming, fishing off the dock and kayaking. Grill dinner on your private deck and watch the stars come out in the evening Or enjoy all that the Berkshires have to offer, Jacob’s Pillow (15 min), Berkshire Theater (20 min), Tanglewood (30 min). There are plenty of nearby hiking trails and charming towns to explore.

Belle Meade

Open concept home with a Zen feel and made for relaxation. Nestle into the covered porch and spend hours of peaceful contemplation with nature all around! When you’ve had enough recharging, plan a backroad trip to endless possibilities. Tanglewood and Jacob’s Pillow are nearby via beautiful country roads. There are hikes for any level. Great restaurants, farmer’s markets and Guidos gourmet market just minutes away. Eat out or stay in with a cook’s kitchen and grill deck.

Beautiful family home, Hike, Fireplace, Sleeps 12

Voted by Airbnb guests as a top "Wish-listed family home" * A beautiful 5 bedroom post & beam house in the woods off the Appalachian trail. * Butternut ski Mountain 15 mins * Roaring fireplace & free firewood * Outdoor fire pit * Great Hikes from the house * Pets welcome * Fast Wifi - Fiber * Great Barrington 15 mins/ local shops * Kids activities at the house & area. * Jacobs Pillow & Tanglewood 20 mins * Fishing, kayaking & Swimming Lake 5 mins

Jaw dropping mountain & lake views

Curl up with a good book by the fire and gaze out at the dreamy picturesque mountain and lake views..... Or ski, swim, hike and enjoy so much more that the Berkshires has to offer in this centrally located Southern Berkshire county home. Private mountain top adventure awaits.. Centrally located in Southern Berkshire County: 10 minutes from Butternut ski, 20 minutes to Great Barrington, 25 minutes Stockbridge & Lenox and 2 ½ hours from NYC and Boston.

Idyllic family retreat - spacious lake home,

This recently renovated waterfront home is perfectly situated close to many Berkshire attractions for an ideal getaway. Lake views are stunning year around. The fire-pit at shore offers a unique outdoor gathering option. Warm and welcoming interior with three levels of living for families and friends (up to 8 people). Area offers family-friendly hiking. Enjoy the whimsical decor and mid-century style furnishings. Cook in the well-equipped kitchen.

HOT TUB! Dog & Family Friendly in the Berkshires!

Secluded Berkshires Retreat! -Dog/s, Family Friendly cottage -Freshly painted & new floors for 2026! -Patio w/ Hot tub, fire pit, canoe use -Acre secluded lot -Historic Lee, Stockbridge, Lenox/Tanglewood, Norman Rockwell Museum w/in 30 min! -30 min Monument Mt. & Berkshires Scenic Railway -Appalachian Trail hiking -Wineries/Breweries -Outlets/Small Shops -Master w/Queen -2nd bed with 1 Twin/Full Bunk -Full size pull out couch

Walk to Town! Great Barrington 4-bedroom farmhouse

Enjoy the yard and garden at this charming 4-bedroom in-town farmhouse. The garden features various fruits and vegetables in season. Stroll to Great Barrington's restaurants and shops. Hike the woodland trail up the hill for a swim at nearby Lake Mansfield. Retreat to the private garden hideaway. This place has something for everyone who wants to relax in a cozy setting yet still be near everything Great Barrington has to offer.

Stylish Mid-century Modern Berkshires Cape

Stylish and design forward, yet entirely comfortable for families and kids. Fully renovated 4 bedroom, 2.5 bath home located in the heart of the Berkshires. Enjoy the large, sunny yard and deck with lots of seating and a large dining table - perfect for al fresco dinner and drinks! The house is decorated in mid century modern style with gorgeous design touches throughout!