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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

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.

Starry Skies, Sauna & Smores: YOUR Fall getaway

Unique Berkshire vacation experience, away from the hustle and bustle: 🍁Boost your wellness in the barrel Sauna 🍁Relax around the grill, pizza oven & firepit 🍁Mingle around our 80” TV & gas fireplace 🍁Minutes to restaurant & hiking 🍁Kayak & swim (weather permitting) 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

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!

North Goshen A-Frame

This beautiful A-Frame is nestled on 4.5 acres in the charming NW corner of Connecticut. Situated adjacent to 800 acres of state forest and just 8 miles from Mohawk Mountain Ski Area, this location offers numerous hiking trails and walking paths, making it a haven for outdoor enthusiasts! Local attractions include: Mohawk Mountain Ski Area, Goshen Fair Grounds, Action Wildlife, Sunset Meadow Winery, Nodine's Smokehouse, Thorncrest Milk House Chocolates, Infinity Music Hall, Lime Rock Park

The Goshen Glass Chalet

A vacation house furnished decorated 1 large master bedroom down stairs and full bathroom.2 bedrooms 1 full size bed upstairs & 2 twin size beds upstairs with a full bathroom bathroom .1 well stocked & equipped kitchen 1 large spacious combined living and a dining room with fireplace and large screened TV.A beautiful outdoor deck that sits 6 people for dining outside 1 screened in porch with a beautiful large patio with a barbecue & fire pit woods view, 10 minute drive to the Lake.

Candlewood Lake Vacation Home | jj chalet

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. Dog friendly w/ fee (must be listed on reservation) 3 bedroom / 2 bath 4 wheel drive vehicles required for winter travel.

"Nirvana": A Lakefront Retreat

Summer is here, now's the time to enjoy a lakefront getaway! Discover our rustic oasis amidst the treetops of Woodstock, Connecticut! Magnificent views in every corner; a spacious open floor plan with kitchen, living room and dining room; 2 private bedrooms; a large outside deck; and gorgeous Witches Woods Lake make Nirvana the perfect place to relax and enjoy nature. IMPORTANT: Nirvana is meant for small, relaxed getaways. Please review the house rules before booking.

Modern Secluded Ski Chalet | 40 Acres | Family

Enjoy privacy at a cozy mountain home on 40 acres, minutes from ski resorts and shops. Floor-to-ceiling windows offer stunning views. This pet-free retreat is ideal for families seeking adventure & relaxation. Kids enjoy the playroom and outdoor space while parents relax in the jacuzzi tub or comfy living area. The fully stocked kitchen makes meal prep simple. Friendly local hosts provide restaurant tips, babysitter bookings and insider advice to enhance your stay.