Holiday houses in Alander Mountain

Chic Cabin in the Berkshires, Mountain getaway!

Find serenity at this cozy cabin set on ten tranquil acres at the end of a dead end road on top of Mt Washington, Massachusetts. This chic cabin is a private, peaceful oasis in the woods. You will find yourself very near the benchmark of Massachusetts, Connecticut and New York with endless hiking trails right outside your door, including The Appalachian trail. You will be at the doorstep of all the culture, shopping and dining that the Berkshires, Litchfield and Columbia County have to offer.

Private upstate home nestled in the Hudson Valley

Recently renovated chalet-style home located in Copake New York 10 minutes from Copake Lake. Modern design meets country living. Centrally located with access to the Berkshires, Hudson, Catamount Ski Resort, Bash Bish recreation area and more! This 3-bedroom, 2-bath home sits on 3.5 acres of landscaped grounds with beautiful western views, garden patio, wrap-around deck, fire pit, modern amenities, central air, and outdoor games. Set back from the road, the property is private and secluded.

TREE FARM Hilltop Getaway: Majestic Mountain Views

Surround yourself with sweeping, unparalleled views in our our bright, cheery 3-bedroom countryside treasure. We're nestled atop 9 acres on a serene country road, directly across from a quaint tree farm and its stunning panoramic backdrop--the Taconic mountain range and valley. Centrally located between Hudson, New York & Great Barrington, Massachusetts. Only 1.5 miles to Copake Lake and roughly 5 miles from Catamount Mountain, we offer the closest proximity to upstate’s very best year-round.

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.

Unique 30 Acre Waterfront Retreat

Spanning 30+ private acres, this waterfront retreat sleeps 14 across 3 buildings. The main house features a renovated open kitchen, dining, and living space with a fireplace, sunroom, and primary suite with an en suite bath. Upstairs, 2 bedrooms sleep 6 and in the basement a gym and living area. The 1960s boathouse has a cozy living area, sleeping for 2 and waterfront deck. The sleeper cottage sits at the water’s edge for a secluded stay. Enjoy nature, privacy, and stunning pond views.

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.

Copake Retreat

Our cozy 3 bedroom home is 120 miles from New York City and 150 miles from Boston. It's located in a friendly private lakeside community with 2 sandy beaches on Robinson Pond. The surrounding area is gorgeous with rolling hills and farms. We're within a half-hour drive from Great Barrington, MA., Hudson, NY, and Millerton, NY. and it's a very short drive to Taconic State Park. Enjoy our 4-season Copake Retreat! The furnishing is comfortable and cozy, but not upscale.

Modern Farmhouse w/ Firepit-5min to Bash Bish

Welcome to Copake, a peaceful, pastoral, hamlet ideally situated between Great Barrington, Mass. and Hudson, New York. This countryside cottage with views of Mount Washington and our expansive wildflower meadow provides the perfect retreat for your time exploring Columbia County and Western Massachusetts. You're a short drive from a host of restaurants, shops, and nature excursions in any direction you choose, not to mention a 12-minute drive to Catamount Ski Resort.

Hilltop Barn - Views, Hot Tub, Plunge Pool, Sauna

A private hilltop oasis in nature. Newly renovated barn with some luxury amenities including sauna & outdoor firepit & movie theater screen & hot tub & stock tank pool on a 15-acre hilltop w/ views & privacy in Hudson Valley / Berkshires. Fully stocked for cooking & tons of games. Near great shops & restaurants in Hudson & Great Barrington. We can point you to the best people to book for private massages or yoga classes right at the house.

Breathtaking Views of Secluded Paradise

Nestled atop a sprawling pasture and surrounded by the rolling Catskills, Casa Lobato Farmhouse offers refined comfort and timeless charm. Spacious yet intimate, this elegant retreat is designed for effortless relaxation with elevated amenities. Take in sweeping views, unwind by the firepit beneath the stars, or hike to a cascading stream. As a certified “Healthy Home,” we proudly provide a stay that feels both indulgent and restorative.

Bright/Spacious Getaway at foot of the Berkshires

Centrally located in the Hudson Valley at the foot of the Berkshire mountains, this is a beautiful duplex. After raising our family in the larger side, we moved to the attached, yet fully separate apartment . We're looking to rent the larger 2,900 sq. ft., 4 bedroom/3 bathroom side, which sits on 1.5 acres with a fenced in backyard and parking area. 60" satellite Tv in big room and two other smaller tvs in master bedrooms.