Chalet holiday rentals in Berkshire County

Find and book unique chalets on Airbnb

Top-rated chalet rentals in Berkshire County

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Superhost

Chalet in Lenox

4.81 out of 5 average rating, 27 reviews

Berkshires Escape | Stylish Chalet + Scenic Views

Elegant, light-filled cabin blending modern comfort with much charm; in Lenox besides Kennedy Park. Enjoy mesmerizing foliage views from the expansive deck, a cozy wood stove and a serene private garden. Main suite upstairs with bath and comfy sitting area; downstairs offers a queen room, twin ensuite, and TV lounge. Perfect luxe Berkshires retreat for intergenerational families. Games, ping pong and top-tier destinations minutes away: Butternut, Bousquet and plenty leaf peeping & hiking options

Guest favourite

Chalet in Otis

4.95 out of 5 average rating, 427 reviews

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

Guest favourite

Chalet in Great Barrington

4.96 out of 5 average rating, 74 reviews

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.

Superhost

Chalet in Otis

4.9 out of 5 average rating, 71 reviews

Starry Skies, Sauna & Smores: YOUR Fall getaway

Unique Berkshire vacation experience, away from the hustle and bustle: 🍁Boost your wellness in the barrel Sauna 🍁Relax around the grill, pizza oven & firepit 🍁Mingle around our 80” TV & gas fireplace 🍁Minutes to restaurant & hiking 🍁Kayak & swim (weather permitting) 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 and more

Top guest favourite

Chalet in Averill Park

4.96 out of 5 average rating, 80 reviews

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. /\

Chalet in Hillsdale

4.86 out of 5 average rating, 64 reviews

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!

Top guest favourite

Chalet in Monterey

4.98 out of 5 average rating, 87 reviews

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!

Top guest favourite

Chalet in Canaan

5 out of 5 average rating, 13 reviews

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.

Chalet in West Stockbridge

4.95 out of 5 average rating, 41 reviews

Secluded Mountain Home 7min from Great Barringtom

Sunlight filled, 3 Bedroom, open-plan home in a quiet mountainside location, but only 7 mins from Great Barrington, 13 mins to Lenox & Tanglewood. Cathedral ceilings, modernly furnished, open, modern kitchen and dining. Screened-in porch for outdoor dining. Enjoy mountain views with endless windows and deck. Fire pit for summer s'mores. Well positioned to embrace the great outdoors all year round - with swimming, hiking, boating, skiing, shopping, etc., ... all within 10 minutes drive.

Chalet in Canaan

4.57 out of 5 average rating, 69 reviews

R3Bliss - Estate with Hot Tub, Tennis Court & Pool

Welcome to Your Perfect Retreat Escape to a serene 15-acre estate in the heart of the Berkshires, where relaxation and renewal are effortless. Designed for peaceful getaways or intimate group retreats, this tranquil haven offers thoughtfully curated accommodations, Private tennis court and pool. Salt water hot tub. 4 bedrooms with queen beds, and expansive landscapes. Immerse yourself in nature, unwind, and gather with loved ones to create lasting memories in an unforgettable setting.

Superhost

Chalet in Great Barrington

4.85 out of 5 average rating, 20 reviews

River Views, Screen 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!

Guest favourite

Chalet in New Marlborough

4.92 out of 5 average rating, 53 reviews

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.