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3BR Guest House on 36 Acre waterfront

3br bedroom Adirondack lodge, complete with wrap around porch on our 36 acre waterfront estate. Updated kitchen with island bar and laundry. WiFi, high speed internet+fire tv. NewCentralAC. Estate featured on HGTV and The Wall Street Journal. “Salem Woods” on Gardner Lake features an amazing shared indoor 8000 sq. Year round:salt water pool & spa, hot tub, sauna, & steam room. Enjoy: walking trails, half a mile of private sandy beach, 2 docks, fire pits, canoes, kayaks, fishing, water sports.

Modern Mtn Chalet | Great Barrington & Tanglewood

Modern 3-BR Mountain Retreat. Sunlight-filled home (dining for 12) with cathedral ceilings in a secluded setting. Summer-ready: Large deck, screened porch, grill, firepit. 10 mins to Great Barrington/Stockbridge. Enjoy Tanglewood (20m), Norman Rockwell Museum (10m), Appalachian Trail hiking, and nearby lake swimming. • Luxury Kitchen: Open-plan & fully equipped • Outdoors: Screened porch, deck & fire pit • Culture: Near to galleries, antiques, historic homes, great dining, & farmer's markets.

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.

Natural Splendor: Forest Luxury Retreat

Discover your perfect retreat near the heart of the Berkshires! This charming house offers tranquility year-round. In autumn, vibrant golds surround you; in winter, enjoy the warm fireplace while snow dances outside. The game room features pool and ping pong tables, and the spacious family room has surround sound and a 65" TV. Relax on the screened porch or large decks, gather around the fire pit, and enjoy a baby grand piano. Close to top attractions and restaurants, your ideal getaway awaits!

Contemporary Rustic Lake Chalet

Chalet surrounded by glass and natural sunlight with cathedral ceilings. Fully stocked and equipped kitchen with island bar and chairs . Dining table seating for 6. Sony large screen TV. Bose surround sound Beautiful fireplace..HVAC over fireplace. Window AC's in bedrooms. Outdoor dining seats 6. Large screened in porch with a beautiful large patio, hot tub, gas grill. Charcoal weber grill & fire pit. Lake with 4 private beaches . 14night stay for pool use. 2 hours from NYC.

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!

Family Lake Retreat | Sauna, Deck & Games

🚣 Kayak, swim, or float on the lake 🧖‍♂️ Relax in the Scandinavian barrel sauna 🍕 Grill, bake in the pizza oven, or gather around the firepit 🎶 Enjoy restaurants and Tanglewood (20 min) All Year Round: The light-filled interior offers comfort and style: 📺 Two large flat-screen TV (75" in Master bedroom, 80" in living room) 🍳 Fully equipped kitchen (air-fryer, waffle maker, Nespresso) 💻 Home office with fast WiFi 🎮 board games and outdoor 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 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.

Waterfront lakehouse in Berkshires

Lovely new lakefront home with beautiful patio and yard overlooking Laurel Lake. Beautiful view of lake from kitchen, living room, loft, patio, and screened-in porch. House has 2 bedrooms plus a large loft with a double bed. Yard includes a dock for swimming. In the winter, enjoy beautiful views of the lake from the cozy living room with oversized windows. Also, easy access to Berkshire skiing! Perfect weekend get-away!