Vacation rentals in West Stockbridge

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Gingerbread House Tower in the Berkshire Hills

Escape to this off-beat retreat for a magical stay. Part of Tyringham’s Gingerbread House located on the Santarella Estate in the Berkshires, Western Mass. This one-of-a-kind loft with tower bedchamber offers guests a fairytale experience. The open concept living space filled with plants brings the outdoors inside and offers ample room to relax. Guests can spend the day exploring numerous nearby towns, lakes, skiing, hiking trails, and various performing arts performances the Berkshires offers

Luxury A-Frame Cabin in the Woods with Sauna

🔨 Heads up: We’re currently making improvements to the property and there’s a chance of construction activity nearby on weekdays between 8am–4pm for the next few months. Evenings, nights, and weekends are completely peaceful and unaffected. 🏡 Modern A-frame in the Catskills with woodland views. Cedar barrel sauna, outdoor shower, smokeless fire table, and wrap-around deck. Queen bedroom with forest views, outdoor fireplace, fast Wi-Fi. Minutes to trailheads, waterfalls, and farmers markets.

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.

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.

Private 2nd-floor studio on a working produce farm

Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or just relax out on the balcony and take in the views.

The Cottage at The Barrington House

Welcome to the Cottage at the Barrington House! The Barrington House is nestled in the serene Berkshires Mountains - which have long been a sanctuary for weary city dwellers seeking breathing space, a perfect retreat for artists, writers and thinkers! It's sprawling grounds offer stunning views of lush valleys and distant peaks, while the interior features a fireplace, cozy reading nook, and unlimited windows that invite the natural world inside.

Artist Cottage

Artsy vintage cottage with a private lodge in a quiet Berkshire neighborhood. Backyard opens to woods with trails nearby. Enjoy fireplaces and hot tub in winter, waterfall and outdoor shower in summer. Upstairs queen ensuite with bathroom and soaking tub; downstairs retro kitchen, living room, and full bath with shower. Lodge offers comfy seating, farm table, and big-screen TV. High-speed internet, Prime & Spectrum TV.

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.