Holiday houses in West Stockbridge

Rustic Secluded Cabin near Berkshires. *wood stove

The Red House offers a peaceful secluded retreat, surrounded by acres of forest & with excellent hiking trails. Enjoy the tranquility of nature while being minutes from antiquing, Kripalu, the Norman Rockwell Museum, The Mount, Tanglewood, skiing, & Shakespeare & Co. You'll appreciate the serene privacy, situated on an old dirt road. Relax by the wood stove or in the sunroom. Nearby towns of Spencertown, Chatham, & West Stockbridge offer unique charm. 4WD vehicle is recommended for winter visits

Pixley Forest | 15 Mins To Tanglewood • Fireplace

Get away to this peaceful Berkshire escape tucked into the woods of Pixley Hill in West Stockbridge! The home boasts 3 full bedrooms as well as a smaller kids room and two extra special twin beds in a fun lofted space that feels like a campout even for the biggest of kids. Enjoy a night tucked in by the fireplace or a lazy Sunday lounging in the tub connected to the master bedroom. If being nestled away in the woods but still only 15 minutes to Tanglewood is your thing, hurry up and book today!

Berkshires Forest Retreat with Hot Tub

A freshly renovated modern home, set on 3.5 private acres at the end of a cul-de-sac is the perfect home base for your Berkshires getaway. Drive 6 minutes to Tanglewood & be in downtown Lenox in less than 10 minutes! Located in picturesque Stockbridge, MA this home is a short drive from Tanglewood, Wineries, Museums, Theatre, Skiing, Hiking, Golf, Shopping and Dining. Enjoy quiet country living, minutes from all Berkshires attractions. Longer stays are welcome. Ask us about monthly discounts!

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.

Secluded Chic Mountain Chalet near Tanglewood

Escape to Tranquility Glade, a newly designer-renovated modern chalet on 5.5 private forest acres near Tanglewood & Kripalu. Bathed in natural light with cathedral ceilings, skylights, and a dramatic stone fireplace, this serene retreat blends modern style with woodland calm. Enjoy curated furnishings, a sleek European galley kitchen, outdoor firepit, tranquil forest views, and easy access to lakes, waterfalls, hiking, and skiing—perfect for cozy evenings or peaceful mornings among the trees.

Sweet Victorian in Housatonic

Fresh and simple living in a three bedroom family friendly duplex. Experience the Berkshires while staying in a newly renovated Victorian house in Housatonic. Tasteful clean furniture, organic new sheets, pillows and duvets. Lovely clean kitchen that is fully equipped to host dinners. Situated up on a hill in Housatonic this three bedroom is conveniently located to to Great Barrington, Lake Mansfield, Stockbridge, Butternut, Catamount, Tanglewood, Kripalu and Monument Mountain.

Luxury Barn Retreat Near Hudson & the Berkshires

Set on eight private acres where New York meets the Berkshires, this architect-designed retreat combines dramatic contemporary design with warmth and comfort. Soaring ceilings, a chef’s kitchen, designer interiors, peaceful outdoor spaces and nearby lake access create the perfect escape. Ideal for couples, families with children or close friends, it’s a short drive from Hudson, Chatham, Great Barrington, Tanglewood and countless other destinations for shopping, dining, hiking and more.

Modern Log Cabin w/Pool & Views By Evergreen Home

Evergreen Home Vacation Rentals invites you to this refined log cabin featuring a heated saltwater pool, hot tub, and mountain views. Just 15 minutes to Butternut, this 3-bedroom (5 bed), 3.5-bath escape boasts a stone fireplace, screened porch, and spacious suites. Outside, enjoy the fire pit, lush gardens, and pool house. Perfectly located near West Stockbridge, Lenox, and Great Barrington, this retreat offers rustic charm with modern luxury. Your private Berkshire getaway awaits!

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.

Peaceful Stockbridge Cabin in the Woods

The Residence is a beautiful, secluded home in the Berkshire foothills. The 14-acre property includes hiking trails through the woods, a meadow, and a lovely babbling brook. Despite its secluded feel, the house just a short drive from many of the area's favorite attractions. The Residence provides a wonderful for base for enjoying all that the Berkshires have to offer, though guests may decide to spend much of their stay exploring the rustic beauty of the property itself.

Historic 1810 Farmhouse - Fully Renovated

Charm and history meet modern convenience in this stunning renovated farmhouse. Built in 1810, this beautiful home was once the residence of Mr. Prince, who presided over the Tobey Quarry Farm. Just steps into town, the cottage is the ideal retreat for a low-key, cozy getaway. Or as a launch pad to the area's many outdoor/cultural offerings. We warmly welcome you!

Guest House near hiking trails and excellent cafés

Studio guesthouse is all yours. In a quiet valley near walking and hiking trails. Close to Tanglewood, the Stockbridge Bowl, and Kripalu. 10 minutes to downtown West Stockbridge and No. 6 Depot Roastery and Cafe. 15 minutes to Great Barrington. The guest house is on owner's property and there is a dog on the premises. Absolutely no pets or children under 18.