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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

Lakefront | Pvt Dock | Kayaks | Firepit | 1G | W/D

The Yellow • 1,750ft² (170m²), 2-level cottage • Open concept with 180° view from living room • 3 bedrooms (all queen size beds), 2 full baths • Fully equipped kitchen • Private dock & firepit • Canoe & 2 kayaks • 50" smart TV and 4 Google Smart Speakers • 1 Gigabit Wi-Fi 'gorgeous with amazing views' • Workspace with laptop stand upstairs • Additional full size bed upstairs • Additional queen size sofa bed downstairs • Additional twin trundle downstairs • Washer and dryer with laundry detergent

Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!

Berkshire 4 season home

The house is located in the heart of the Berkshires. It's less than 10 miles from Tanglewood, Kripalu, Jacob's pillow Dance, Monument Mountain, Beartown state forest, Norman Rockwell Museum, Shakespeare & Co., Ski Butternut, Lee Prime outlets. Located 1.5 miles from the turnpike exit for easy travel, 3 miles from Laurel lake, walking distance to a public golf course and downtown Lee where you will find great restaurants. There is Cable internet that is fast and reliable if you have to work.

Artist Cottage

Enchanting, private, romantic, retro style, artsy, cottage & lodge building with fireplaces and outdoor hot tub and shower area in a quaint, quiet, neighborhood nested at the base of Flag Rock and near nature trails and downtown Great Barrington. Perfect for a romantic get-away. Open retro style kitchen with wood stove and TV is stocked with utensils and pans for cooking with gas oven and retro appliances. Upstairs bedroom with ensuite large bathroom with soaking tub and message chair.

Hillside Haven

Ideally located on “the hill” in a beautiful and quiet neighborhood just a short walk to downtown Great Barrington’s amazing cafes, restaurants, ice cream, and Lake Mansfield’s beach and loop trail. The perfect hillside haven for those looking to be in the center of it all. This private, modern, and clean space is completely new as of mid-2021 and has a well-appointed kitchen, outdoor patio with a firepit, fast internet, covered parking, radiant heat floors, and an air conditioning unit.

Double 3 Bedroom Tree House in the Berkshires

Escape, unwind and recharge in this double treehouse. A live tree runs through the interior connecting you directly with nature while in the comfort of home. Built with refurbished, materials and hand curated with care and love. Feel like you’re in the middle of nowhere, yet it’s only minutes to the town of Great Barrington for shopping dining or just a walk around town. Use these dreamy separate spaces for sleeping, writing or drawing in peace. LGBTQ+ owned and operated.

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 relax by the firepit- we hope you enjoy your stay and will visit us again.

Best of the Berkshires + Hot Tub by Evergreen Home

Ski, hike, shop, and dine with this beautiful 2-bed, 1-bath Berkshires cottage as your home base. 7 minutes to downtown Great Barrington, this stylish, cozy rental has everything you need for a great getaway. A new renovation brings modern amenities to this classic 50’s cottage. Enjoy a chef’s kitchen, 500 sq-foot deck with hot tub, and thoughtful touches like yoga mats, a record player, board games, and a backyard hammock. Monthly ski rental discounts are available!