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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

The Lookout

Massive 4,000 sq foot chalet on more than seven acres. Only 90 minutes from NYC, with incredible mountain views and stunning sunsets. Floor-to-ceiling stone fireplace, outdoor firepit, 8 person hot tub, and gas grill for use. Private hiking trail on property. Close proximity to all of Hudson Valley's best golf courses, breweries, wineries, hiking trails, parks, and ski resorts. Easy drive to historic Beacon, Cold Spring, Rhinebeck, Pawling, and New Paltz, and only minutes away from Metro North.

Berkshire "ZEN" Chalet

"ZEN" Palace Chalet perfect spot to chill & relax after a day of exploring or skiing. SPACIOUS,secluded,quiet, great grounds -3 bdrm 2 ba with LUSH VIEWS endless windows. BEAUTIFUL exposed wood beams & ceilings throughout. Super family friendly. 5 min GREAT BARRINGTON, Butternut, Catamount, great food, nature trails, lakes, great shopping & farmer's markets. Close to STOCKBRIDGE,Tanglewood, Norman Rockwell Museum, Wheatleigh, Kirpalu,Canyon Ranch & HUDSON NY. Accessible knowledgable local host.

Peaceful Chalet in the Woods: Walk to Lenox

Family friendly, spacious cabin. Tons of natural light a wood stove and private garden. Woodsy feeling in contemporary setting next to Kennedy Park. Downstairs is mobility friendly w/ 1 twin ensuite, 1 Queen w/ separate full bath & TV room. Upstairs: Main bedroom with w/separate full bath and sitting area. Lovely deck, stunning views. Ping pong table and plenty of games for kids! 10 mins drive to Tanglewood, Kripalu; 8 min drive to Bousquet Ski Mtn., 15 to Red Lion & 25 to Butternut Mtn.

Cozy French Country chalet

Perfectly situated, this cozy French Country chalet is minutes to downtown Monterey, Lake Garfield & just 10 minutes to Butternut for skiing. Family friendly, this home is stocked with games, movies & books for a fun-filled trip. If you're looking for a relaxing Berkshires getaway, look no further than this well-cared-for home, stocked with amenities to make your trip comfortable & relaxing! The home also has upgraded Internet with 2 internet satellite dishes, to handle Zoom calls & home work!

Secluded Lakefront Chalet-Firepit&yard Dogfriendly

Take it easy at this unique & tranquil getaway just over 1 hour from Nyc. 200 feet of private lake front all yours to enjoy. Secluded, modern chalet & fireplace. King size bed. Spacious bedroom & bathroom. Farm style dining table, sofa & daybed in open concept living room. Desk & lounge area with record player, karaoke & TV. Large sun room with comfy daybed & gorgeous lake views. Lakefront dining & swing. Fenced yard, deck,fire pit,bbq. Lots to do nearby! We❤️dogs. Serenity awaits!

Kayaks, Sauna & Family: Relax & Play

Join our unique Berkshire vacation experience, away from the hustle and bustle: 🌟Kayak & swim on the lake 🌟Boost wellness in our barrel Sauna 🌟Relax around the gas grill, pizza oven & firepit 🌟Minutes to restaurants & hiking 🌟Entertainment at Tanglewood (20 min) The newly designed light-filled interior offers comfort and style while being perfectly suited for children: 👉fully equipped kitchen (air-fryer, waffle maker, Nespresso) 👉home office (Fast Wifi) 👉arcade-style games and more

Hudson Valley Lakeview Retreat - Lake Access

Relax and enjoy nature in this lakeside retreat! Only 75 minutes from Manhattan, with Metro North access nearby. Wake up to the sunrise over the lake with stunning views from the master bedroom; enjoy the private lake or one of many nearby hiking & biking trails; cook in the fully equipped kitchen or outdoor grill; and wind down with a bath in the jetted tub and a fire in the indoor wood stove or outdoor fire pit. UPDATE: Summer Lake view is back! Freshly trimmed trees and bushes.

jj chalet | Candlewood Lake Vacation Home

Modern A-frame home on the northern end of Candlewood Lake in New Milford, CT. Only 1.5h drive from NYC, making this the perfect nature escape for families or small groups . Whether you're taking out the kayaks, going for a hike on miles of open trails, or relaxing by a cozy fire on the deck, you're bound to make some incredible memories here at jj chalet. Pet friendly w/ fee (must be listed on reservation) 3 bedroom / 2 bath 4 wheel drive vehicles required for winter travel.