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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.

StrautmanHaus: All-Season Chalet at Berkshire East

Welcome to StrautmanHaus, a Bavarian style A-Frame home, nestled at the base of Berkshire East Mountain Resort. This charming chalet is newly renovated, with 4 beds/2 baths/4 decks and stunning views that sleeps 10! Surrounded by mature growth pine trees, the property offers a perfect combination of privacy and ski-on/off access to Berkshire East. In the summer & fall, you have on-site access to the resort’s mountain biking/white water rafting/zip line/mountain coaster & aerial adventure park.

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

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 swim pond (seasonal) • 120+ acres of private trails • Dog-friendly • Starry skies, total quiet, complete privacy • Second house available for larger groups • Local attractions: skiing, kayaking, white water rafting, zip-lining, and mtn biking

Cozy Winter Chalet I Close to Ski & Downtown Lenox

Your Modern Berkshires Ski Escape Elegant, light-filled chalet beside Kennedy Park. Sleek design meets comfort with a mesmerizing view, spacious living room, and a serene garden. Main suite upstairs with bath and comfy sitting area; downstairs features a queen room, twin ensuite, and cozy TV lounge. Stylish winter Berkshires retreat for intergenerational families. Minutes to Lenox dining, Butternut & Bousquet skiing— snow-shoeing, ping pong and top-tier destinations minutes away. Healthy fun!

Modern Mtn Chalet | 7m to Great Barrington & Ski

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.

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

Screened Porch, River Views, Center of the Berks!

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

Sleek Butternut Ski Chalet Lakefront HotTub Sauna

Newly Renovated Berkshires chalet with HOT TUB & Sauna, Pet friendly, 5BR 4 full bath on Lake Garfield 5 min to Ski Butternut, 15 min to Ski Catamount, 15 min Great Barrington dining /shops. Spacious, family-friendly home sleeps 14 with 2 living rooms, out door hot tub for 6, indoor infrared sauna, wood fireplace, BBQ, Solo fire pit sitting 6, fenced yard, decks, and 2 kayaks. Short walk to lake beach. Perfect for ski trips, lake stays, and group and family getaways.

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.