House holiday rentals in Hancock

Rustic Swedish Barn/Featured in Airbnb Magazine

Enjoy expansive views of the Catskill Mountains from this stunningly renovated Scandanavian barn. Featured in more than 10 magazines and catalogues, including AirBnB Magazine! Walk the property, with its big open fields, an organic orchard, walking paths, and flower gardens. A large private pond is swimmable (after heavy rains it does get muddy). The Barn has central heat and air conditioning. A full bathroom features an antique bathtub. Enjoy dining inside, or outdoor grilling and dining.

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.

Cleveland House - renovated Berkshires' gem.

Enjoy a retreat in a home full of history - it was a tavern/stage coach stop in the 1800's. Today we have added modern comfort while keeping the charm. We are centrally located in the Berkshires making it easy to enjoy -ski Jiminy, hike Mt. Greylock, and enjoy the culture. Or stay in and unwind. Play games on the flat 3-acre yard or try yoga surrounded by nature. Work remotely in our library. Walk down our country road and enjoy the farms. Most of all, reconnect with family/friends.

Brooksong, the perfect Berkshires getaway

Part of this bright, sprawling, five-acre property was built in 1866 as a schoolhouse. Its historic charm now includes all the updated comforts of home, in an idyllic country setting that's lovely in all seasons. Located a short drive from Jiminy Peak, Brooksong is perfect for a ski vacation and close to plenty of lakes for summer fun. With a pool table, fire pit, and play set for kids, this is the perfect place to recharge and have fun with the people you care about. Welcome to Brooksong!

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!

Lakefront escape w/ Breathtaking Bald Eagle Views

Wake up to bald eagles soaring past floor-to-ceiling windows in the lakefront great room. Relax by the fireplace or unwind in the cozy TV room. A spacious kitchen makes cooking easy. Upstairs: 4 bedrooms (2 king, 2 queen, all w/ desks) + 4 full baths (3 w/ showers, 1 w/ tub). Enjoy fast Wi-Fi, seasonal lake access, dock, and deck. Swim or kayak at your own risk (no guest boats at dock per insurance). Your lakeside getaway awaits! Airbnb has a strict NO Events policy which we follow.

North Adams Getaway-walk to MASS MoCA

BRAND NEW! Ready for guests to enjoy all the Berkshires has to offer! Whether you are visiting for work or pleasure, with family or friends this is a perfect place for you. Located in downtown North Adams you are surrounded by breath taking mountains and foliage, nestled between award winning museums, access to great food, and a short drive to ski resorts, breweries, Tanglewood, the highest peak in MA, and more. A true outdoorsman paradise. BOOK NOW!

Berkshire Bliss- 6BR/Minutes from Jiminy +38 acres

38 beautiful, private acres of Berkshire woods, cleared land, and mountain scenery. 6 comfortable bedrooms and 4.5 bathrooms. 9 Minutes from Jiminy Peak Ski Resort. 5 Mins from The Lake House cottages. Warm and cozy, modern gem. 4 Fireplaces, multiple hang out areas, napping areas, sauna, jacuzzi, outdoor fire pit, views in every direction, two fridges, high speed internet, plus a kid cave in the basement. Perfect for all four seasons.

Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi

This charming location is perfect for a weekend (or longer!) getaway. With enough sleeping arrangements for 5 people, the cabin is ideal for a couple or a small group of close friends/family. Linens and toiletries are provided, as well as a fully stocked coffee bar. Escape from the everyday & enjoy experiences like Art Omi, local wineries, downtown Hudson & Chatham, skiing, hiking and so much more!

Cozy Modern Sugar House with spectacular views.

This beautiful Vermont home sits on 25 acres with spectacular views. We moved this sugar house structure to this land and had an architect adapt it to its surroundings. It has three walls of windows that display the amazing views. The house is surrounded by Mount Anthony hiking trails and a gorgeous pond. The location is a 5 minute drive to town or a lovely 20 minute walk.

Steps to MoCA private house + SAUNA! Near SKI

Yes, the house is entirely private! 4 bed/1 bath home tucked away at a historical estate in central North Adams. Outdoor sauna, fire pits, gardens. Just a 5-minute walk to MASS MoCA, 10 mins by car to Williams & Clark. Your stay sponsors pro bono residencies for refugee & immigrant musicians. Nearest ⛷️ SKI resorts: Jiminy Peak, Berkshire East Mountain and many others.

Tranquil mid-century modern Berkshires retreat

We love the Scandi House because of its simplicity, openness, warmth, comfort, trees, space, privacy, and convenience. We enjoy this Berkshires retreat for its close proximity to all what Berkshires has to offer in music, arts, and outdoor activities. Most of all, we treasure the tranquility and each other when we are here at the house in the woods.