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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.

Chalet On The Hill

Escape the everyday in this hand-crafted timber frame chalet home nestled into the foothills. Tucked into the back of a private forty acres, surrounded by gardens, woodland, pasture, and thousands of acres of protected conservation land, you won't believe you're only seven minutes from downtown Amherst! Wether you're exploring the beautiful western Massachusetts, visiting family at UMass or Amherst colleges, or simply looking for an idyllic country retreat, there is something for everyone!

Berkshire Fall Chalet | Sauna, Lake & Firepit

Trade busy days for crisp Berkshire mornings at a stylish chalet set on 3 private wooded acres near Benton Pond. Designed for families and groups, it sleeps 10 in 5 bedrooms. 🧖‍♂️ Unwind in the Scandinavian barrel sauna 🔥 Gather by the firepit or gas fireplace 🛶 Enjoy seasonal lake access and nearby hikes 🍕 Grill, bake in the pizza oven and stocked kitchen 🎶 Discover local restaurants and entertainment 🎮 Board games and outdoor fun 💻Work easily with fast Wi-Fi, office and EV charger

Modern Mtn Chalet | Great Barrington, Fall Foliage

Modern 3-BR Mountain Retreat. Sunlight-filled home with cathedral ceilings and a spectacular view of fall foliage in a secluded setting. Deck, screened porch, grill, fire pit. 7 mins to Great Barrington, Stockbridge. Enjoy farmers’ market, Norman Rockwell Museum, Appalachian Trail hiking, and apple picking. • Luxury Kitchen: Open-plan, fully equipped • Outdoors: Screened porch & fire pit • Fireplace • Culture: Near to great dining, historic homes, antiques, galleries, & fall festivals.

Ski, Raft & Relax | Lodge w/ Pool Table & Fire Pit

On your journey to The Lodge on Warner Hill, you will pass through a nostalgic covered bridge, drive by a babbling brook, and meander up a winding dirt road. Our home sits in a quiet, peaceful 5-acre setting. It has been completely remodeled with earth-tone charm. Enjoy your time with friends and family relaxing, reading a book, playing pool, barbequing on the back deck, gazing at the stars, or hanging out by the fire pit. Located 10 minutes from Berkshire East and the Deerfield River

Sunset River Views, SIP, Spotless, Sleeps 8

Conway House: Conway House: Brand New Contemporary Chalet with 3 Bedrooms, 2.5 baths and sparkling river views! Sleeps 6 (8 max). Screened porch, central AC, propane wood stove, 2 HDTVs, 2 car garage with direct entry, propane grill, outdoor seating with solo wood stove, high speed internet, good cell service, washer/dryer, whole-house water filter for clean drinkable water, decks with river views and plenty of outdoor seating! All linens included. Pets considered. No Smoking, please!

Modern Chalet Near Tanglewood & Downtown Lenox

Your Modern Berkshires Escape Light-filled modern chalet next to Kennedy Park with beautiful views, a spacious living room, and a peaceful garden for morning coffee, evening wine or yoga. Designed for families and friends, with a private upstairs main suite plus comfortable guest rooms. Minutes to Tanglewood, downtown Lenox, hiking trails, lakes, great dining, and the best of the Berkshires. Perfect for a summer getaway filled with music, nature, and time to unwind. Healthy fun!

Joia Verde| Dog-Friendly Mtn Cabin| Trails| Ski

Joia Verde Mtn Retreat, a private 120+ acre Berkshire retreat surrounded by forest, trails, and a serene pond. This secluded hideaway offers true peace, quiet, and space to reconnect with nature. Highlights: • Fire pit & outdoor seating • Natural pond (seasonal) • 120+ acres of private trails • Dog-friendly • Starry skies, total quiet, complete privacy • Second house available for larger groups (additional fee) • Local: skiing, kayaking, rafting, zip-lining, and mtn biking

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 high-speed broadband internet, capable of streaming & more!

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.

Berkshires Chalet Natural Setting Deck & Fire Pit!

Relax with the whole family at this peaceful 4 bedroom 3 bath chalet as your base to enjoy the great outdoors of the Berkshires. Close to lakes, hiking trails and just a short drive to Tanglewood and Jacob's Pillow. In winter Ski Otis Ridge a mile away, or a 25 minute drive to Butternut. Relax and enjoy family time in the open plan living space with wood burning stove and deck, or venture down to the firepit in the large secluded yard.