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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.

A Hidden Sparrow

/\ Keeping it cozy, yet modern. Our take on hygge minimalism. A Hidden Sparrow is a classic mid-century A-frame nestled on 60+ acres for hiking and has a picturesque creek that flows in the front of the property. With fresh upgrades, tasteful aesthetic and comfy accommodations, A Hidden Sparrow is an idyllic sanctuary offering complete privacy for your next getaway. This all season escape is the perfect place to disconnect from your typical dwelling and enjoy everything nature has to offer. /\

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!

Modern Mtn Chalet | Great Barrington & Tanglewood

Modern 3-BR Mountain Retreat. Sunlight-filled home (dining for 12) with cathedral ceilings in a secluded setting. Fall foliage galore: Large deck, screened porch, grill, firepit. 10 mins to Great Barrington/Stockbridge. Enjoy farmers’ markets, Norman Rockwell Museum, Appalachian Trail hiking, and nearby apple picking. • Luxury Kitchen: Open-plan & fully equipped • Outdoors: Screened porch, deck & fire pit • Culture: Near to galleries, antiques, historic homes, great dining, & fall festivals.

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

Berkshires Vacation Home 6BR, 4 ski mtns, sunsets

A getaway at the edge of the Berkshires - family friendly, 4 ski mountains nearby, charming towns, fireplace, expansive deck, sunset views, private in-ground pool, BBQ, secluded, wooded, nearby lakes, hiking, Tanglewood for summer music and performance festivals. We've set up this vacation home for ourselves to enjoy, so you know we've put our hearts into it and are excited for you to create memories for a lifetime. The home is set up beautifully for families and groups of friends.

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!

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.