Ferieboliger med pool i Berkshire County

Mountain Serenity 20 Acres, Hot Tub, Jiminy<10min

Private Berkshires 20Acre estate designed by acclaimed architect and author Norton Juster. An exclusive 4 bedroom retreat, with mountain views from every room, cathedral ceilings, cozy fireplaces, elegant living spaces, and outdoor fire pit, it’s the perfect place to unwind. Relax in the hot tub or sauna after a day of skiing at Jiminy Peak or Bousquet. Newly renovated with high end furnishings and chef's kitchen. A perfect mix of adventure and tranquility awaits—book your mountain escape today!

Berkshire Getaway Ranch 3 acres + saltwater pool

Escape to the Berkshires in my newly renovated home sitting on 3 acres of land with in-ground saltwater pool. Enjoy the private, rural feel at this property with picturesque sunsets on the hills beyond. Under 5 min to Onota & Pontoosuc lakes, 15 min to Jiminy Peak & Bousquet ski resorts & a short drive to Lenox/Williamstown/North Adams. Light a fire in the living room or master bed & enjoy the cozy ambiance of the vaulted wood ceilings & large picture windows framing views of the bucolic hills.

The Catamount Ski Haus with Pool & Hot Tub

Welcome to the Berkshires! Located almost across the street from the Catamount Ski Resort - come unwind with some fun, peace and adventure. This 4 bedroom 4 bath sits on a 5 acre property nestled amongst the trees with a private pool, hot tub and Mountain View ’s to gaze at. Dine at the quaint, hip restaurant in little cat lodge next to the ski resort, have coffee in Hillsdale at Cook& Larder. Or check out the shops in Great Barrington. There is a ton to do in the Berkshires all year long!

Berkshire Mountain Retreat

Studio apartment with private entrance nestled in bucolic Richmond. Located on a quiet mountain road adjacent to miles of hiking and biking trails. Close to 4 ski areas and minutes to Tanglewood, Kripalu, Clark Art Museum, Mass MoCA, Hancock Shaker Village, the Mass Audubon Wildlife Sanctuary and more. A short drive to Lenox, Stockbridge, and Great Barrington where shopping and fine dining await. Your relaxing vacation begins here with an expansive yard, views and in ground pool!

Stunning luxury home with pool

Welcome to our weekend home in the Berkshires! We now rent it out when we’re not there, following a top-to-bottom renovation with all new furniture, and hope our guests enjoy it as much as we do. Our home is in Great Barrington, 2.5 hours' drive from NYC, surrounded by trees and parkland (Monument Mountain is next door). Yet it's less than 10-15 minutes' drive to town, shopping, restaurants, skiing, and Tanglewood. Come enjoy the Berkshires with complimentary gourmet coffee!

Hollywood Bungalow in the Berkshires #C0191633410

Cool Cozy Rustic Country Bungalow with Screening Room on filmmakers/artists' enclave that's well-located in clean and beautiful Williamstown, near incredible Hiking Trails, Farms, Skiing, MASS MoCA, Clark Art Institute, Williams College, with Pool access, Cable & Smart TV, Porch and Patio, Grill, Fire Pit, Piano Bar Outbuilding with stereo & its own WIFI, First Floor Bathroom with Jacuzzi Bathtub, Laundry, fast WIFI, and lots of outlets in a quiet area on a quiet street.

Bougie B’s Mountainside Getaway

Escape to our updated 2-bedroom, 2-bath condo at Jiminy Peak! Perfectly situated for the ski season, you'll enjoy quick access to both the slopes and apres ski. After a day on the trails, unwind at nearby restaurants like Christianson's Tavern or Bluebird & Co, offering top notch local eats. Bougie B's features updated amenities and that perfect touch of class to make you feel special. Come experience the beauty of the mountains today—your perfect escape awaits!

Perfect Base for Your Berkshire Adventure

Charming private guesthouse with shared pool use. Newly renovated, the space features high ceilings, queen sized bed, rustic Arts & Crafts furniture, heat/air conditioning, and kitchenette. Located in an outbuilding on the property, the guesthouse is close to woodland hikes, excellent biking, as well as many other attractions in the Berkshires. The beautiful in-ground pool is perfect for an afternoon dip - guest hours are usually between 3 - 5.

Hillsdale Escape | Pool, Hot Tub, Game Room

Escape to this beautifully restored 7BR farmhouse nestled in the rolling hills of Hillsdale. Just minutes from Catamount ski area and close to Great Barrington, this spacious retreat features a private pool, 7-person hot tub, arcade game room, fire pit, and chef’s kitchen. Ideal for family reunions, group getaways, team business trips, or peaceful weekends in nature -complete with fast Wi-Fi, Smart TVs, and room for 14+ guests.