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Pool & Hot Tub Escape • Hudson Valley-Berkshires

A stylish 4-bedroom farmhouse, thoughtfully designed with modern comfort and historic charm. Located where the Berkshires meet the Hudson Valley. Surrounded by mature trees, the house offers multiple spaces to gather, with a chef’s kitchen, a den/family/children’s room, outdoor dining, a hot tub, and a generous yard. Minutes to Great Barrington’s dining, lakes, and hiking, and about 30 minutes to Tanglewood and Hudson — the Catamount House is an ideal year-round escape for families or friends.

Cheerful 3-bedroom cottage with woodstove.

Relax with the whole family at this peaceful Berkshire getaway with easy access to all the area has to offer. A quick 20-minute drive to Butternut or Catamount ski hills, as well as downtown Great Barrington. Tanglewood and Jacob's Pillow are a half-hour's drive. Or stay at home and enjoy the peace and quiet of the surrounding woods, light a fire in the woodstove, cook in the large fully-equipped kitchen or head out back to barbecue on the large deck and play a game of badminton in the yard.

Best of the Berkshires + Hot Tub by Evergreen Home

Evergreen Home Vacation Rentals invites you to this stylish 2-bed, 1-bath cottage, just 10 minutes from Catamount and 7 minutes from Great Barrington. This renovated 50s gem features a chef’s kitchen and a 500 sq. ft. deck with a private hot tub. Enjoy thoughtful touches like yoga mats, a record player, and a backyard hammock. Whether you're here to ski, hike, or shop, it is the perfect Berkshires base. Monthly ski rental discounts are available! Inquire today to secure your winter escape.

Kayak on Prospect Lake, Paddle Boards, Swim Dock+!

Due to last minute Cancelation, August 2026 dates available - please inquire! Amenities: 3 bedroom, 1 bath, sleeps 5 or 7 max. waterfront direct on Prospect Lake with dock and swim ladder, sun deck, bar and seating, propane BBQ grill, 2 kayaks, 2 canoes, 2 paddle board, floats. fishing rods, outdoor dining, exterior lighting, fire pit, central AC, washer/dryer, dishwasher, gas fireplace, and more! Quiet, well trained dogs welcome with a $150 pet fee, per pet. Strict on-leash laws apply.

Jug End Crest | Fireplace • Sunroom • Central Air

Welcome to your perfect getaway in the Berkshires! Nestled beside Jug End Reservation and the Appalachian Trail, this modern home boasts valley views and a cozy fireplace in the main living area. After a day of outdoor adventure, relax on the screened-in porch or enjoy the outdoor dining area, complete with a grill for meals outside with family and friends. Experience the unique charm of this one-of-a-kind retreat—your special escape awaits! Book now for an unforgettable experience!

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.

Secluded Mountain Getaway with Swimming Pond.

This is the perfect country getaway in a serene wooded setting yet close to town. Great for couples, solo adventurers, and families (with kids). A large deck and yard provide great views of the outdoors. This house is privately set but only a short walk to an inviting shared swim pond, meadow & trails. Area attractions include great hiking, skiing, restaurants, breweries, stores and markets. Near Great Barrington & Hudson and all the Berkshires and Hudson Valley have to offer.

3-bedroom Berkshire bungalow on 2.5 peaceful acres

Modern farmhouse bungalow with private bridge and brook! Offering privacy as well as nearby nightlife, set upon 2.5 acres of beautiful Berkshire landscape but only 7 minutes to downtown Great Barrington and a short drive to Catamount and Butternut ski area. Mountains, waterfalls, countless hikes and bike routes, farmers' markets, coffee shops, breweries, Shakespeare and Co, Tanglewood, and world-class restaurants all come together in this quintessential New England community.

Modern Farmhouse 5 minutes from Great Barrington

Completely updated with style, this shingled farmhouse combines modern decor with the charm of a country home. Enjoy a spacious, sunny kitchen that connects to a large outdoor patio featuring a fireplace. The cozy living room has a TV for streaming. The first floor includes a bedroom with an attached bathroom & laundry. The second floor suite boasts cathedral ceilings and a luxurious jet-powered shower. This home offers a perfect blend of comfort and elegance for your stay!

24 Main - The Egremont Village House

Welcome to the Berkshires! A large two family home nestled in town center. This space can accommodate multiple families or group of friends for a memorable vacation right in the heart of Egremont on Main Street. Equipped with two kitchens two living rooms, screened in porch outdoor patio and large yard, This house has all you need and more and the location couldn’t be better. Walking distance to restaurants and shops. And it's a short 5 minute drive to Great Barrington.

Seekonk Hill

Great Barrington countryside is waiting for you at this 2-bedroom house, nestled in a serene setting surrounded by conservation woodland and farm pasture. Walk down the winding driveway and find yourself one of the southern Berkshires’ finest walking and cycling routes. The property’s perennial gardens and maintained apple orchard offer brilliant flowers in the spring and summer and apple picking and foliage in the fall. Come enjoy each season's unique brilliance.

Catamount, Zip Line, Private Setting, Book Now!

Expertly renovated four bedroom house with views of Catamount, post and beam wood ceilings and a lovely centerpiece fireplace. High ceilings, renovated kitchen, perfect outdoor space and under a mile to Catamount Mountain for skiing in the winter and zip lining during the summer. Located on a private road with several restaurants within a five minute drive and only eleven minutes to downtown Great Barrington. Bring your family and your furry friends too and enjoy!