Chalet holiday rentals in Berkshire County

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" Cottage

"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.

Cozy Winter Chalet I Close to Ski & Downtown Lenox

Your Modern Berkshires Winter 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. Perfect stylish Berkshires retreat for intergenerational families. Minutes to Lenox dining, Butternut & Bousquet skiing— games, ping pong and top-tier destinations minutes away. Healthy fam fun!

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. /\

Secluded Mountain Home 7min from Great Barringtom

Sunlight filled, 3 Bed, 2.5 bath, modern, open-plan home in a quiet mountainside location, only 7 min from Great Barrington, 13 min to Lenox & Tanglewood. Cathedral ceilings, modernly furnished, well equipped kitchen with dining for 10. Enjoy mountain views with endless windows, screened porch and deck sitting with the trees. Fire pit for s'mores. Embrace the outdoors in any season - with apple picking, leaf peeping, skiing, sledding, spas, shopping, swimming, hiking etc., all 10 min drive.

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!

Thrill & Chill: Ski & Sauna in Winter Wonderland

Join our unique Berkshire vacation experience, away from the hustle and bustle: ❄️Minutes to ski (Otis Ridge), 20 min to Butternut ❄️Boost your wellness in the barrel sauna ❄️Relax around the gas fireplace ❄️Binge your fav show on the 80” TV ❄️Min. to restaurant & snow shoeing 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

SRC-Hudson Valley/Berkshires Cultural Corridor

We welcome you to explore the magic of Sunset Ridge Chalet (SRC). Ideally situated in the Hudson Valley/Berkshires cultural corridor, SRC offers unparalleled panoramic sunset views of the mountains and rights to Queechy Lake. On 7 private acres the Chalet offers the unique opportunity to disconnect from our busy lives and reconnect with ourselves, family, or friends. Imagine starting the day with sunrise yoga on the enormous mahogany deck and ending it with sunset cocktails on the same deck.

River Views, Screened Porch, Sun Deck, Fire Pit!

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!

Ski Cottage in the Berkshire hills

Ten minutes from Jiminy Peak, but surrounded by woods. Perfect for a family ski getaway or a small group of friends, our cottage features a cathedral ceiling in the open living/dining area. There's a galley kitchen & a table for six. There are 3 bedrooms (two double, one twin), one full and one half bath. There's a washer dryer by the entryway and baseboard heating in every room. The nights are starry and tranquil, and the days reveal the beauty of the Berkshire mountains.

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.

Updated Berkshires Chalet Mins to Tanglewood/Lenox

Our place is 4 miles to Tanglewood, and very close to Berkshire Attractions, Skiing, Swimming / Boating, hiking, Summer Theater, Restaurants. Easy On/Off Mass Pike & Taconic Parkway. You’ll love our place because it's newly renovated, open concept two story great room - new kitchen with soapstone counters and SS appliances, screened porch for relaxing in the summer, central A/C, Beautiful secluded grounds. 7 person covered outdoor hot tub; Water Filtration System.