Chalet holiday rentals in Massachusetts

Find and book unique chalets on Airbnb

Top-rated chalet rentals in Massachusetts

Guests agree: these chalets are highly rated for location, cleanliness and more.

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Guest favourite

Chalet in Otis

4.94 out of 5 average rating, 350 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

16–23 Apr

£337 per night

Guest favourite

Chalet in Great Barrington

4.94 out of 5 average rating, 53 reviews

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.

1–8 Jan

£269 per night

Guest favourite

Chalet in Charlemont

4.98 out of 5 average rating, 42 reviews

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.

4–11 Oct

£464 per night

Guest favourite

Chalet in Orange

5.0 out of 5 average rating, 18 reviews

Spectacular Lakefront 3br House, AC, private beach

Perfect nature lover’s lakefront getaway on a private 3 acre peninsula with private beach. This 3200 sq ft home boasts: • Full kitchen w/ SS dishwasher, microwave, range & refrigerator • Three bedrooms • Three full bathrooms w/showers • Air conditioning in every room • Washer/dryer • High-speed WiFi • Deck with built-in grill & patio furniture • Brand new game room with pool table & bar • Parking • 180° stunning lake views • Private beach on the property with floating dock, canoes & fire pit

3–10 May

£535 per night

Chalet in West Stockbridge

4.8 out of 5 average rating, 15 reviews

Tranquility Glade - Tanglewood in minutes

Brand new renovated & back on Airbnb after 6 years! In a secluded woodland setting, this 2023 completely renovated contemporary chalet, set on 5.5 acres, only 7 minutes from Tanglewood and 1 mile to quaint West Stockbridge (and its famous coffee roaster). Open floor plan flooded with natural light, spectacular fieldstone fireplace, cathedral ceilings, skylights. All new stylish furniture & artwork. New European galley kitchen. Revel in the peaceful forest environment that is Tranquility Glade.

8–15 Aug

£555 per night

Guest favourite

Chalet in Cummington

4.86 out of 5 average rating, 101 reviews

Berkshire A-Frame Chalet!

Our secluded home is just off of route 9 in Cummington. We are less than 1 hour away from many attractions including Tanglewood, Mass MoCA, Glendale Falls and Northampton. This area is not only beautiful for hiking, but also motorcycle riding here is exquisite! No wifi or cable (plenty of movies!), good cell phone coverage for Verizon and AT&T (tMobile has not worked in the past, but recently guests have said that it does work). Friendly pets welcome! 1 pet maximum. We abut Shire Village Camp.

6–13 Jul

£162 per night

Guest favourite

Chalet in Monterey

4.97 out of 5 average rating, 73 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!

29 Dec – 5 Jan

£202 per night

Chalet in Lenox

4.7 out of 5 average rating, 10 reviews

Spacious & Private A-Frame Chalet near Tanglewood

Lenox A-Frame with “million dollar” views, in close proximity to Tanglewood & Kripalu. Enjoy a peaceful place w/ high ceilings, lots of natural light, a wood stove and a bright open layout. The 1st fl. is mobility friendly & perfect for elderly guests - 3 bedrooms, 3 bathrooms and modest large kitchen. The cabin is contemporary & *fully furnished* incl. outdoor furniture. Yogis, music and nature lovers - you are steps away from Kennedy Park & Undermountain Horse farm. Kid & Dog friendly.

14–21 Sept

£440 per night

Superhost

Chalet in Otis

4.89 out of 5 average rating, 35 reviews

Lake, Kayaks & Sauna - Family & Wellness

Join our unique Berkshire vacation experience, away from the hustle and bustle: 🌟Kayak & swim on the lake 🌟Boost your wellness in our barrel Sauna 🌟Relax around the gas grill, pizza oven & firepit 🌟Minutes to restaurant & hiking 🌟Have fun at Tanglewood (20 min) 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 (1Gbps Wifi) 👉arcade-style games and more.

27 Oct – 3 Nov

£503 per night

Guest favourite

Chalet in Charlemont

4.98 out of 5 average rating, 53 reviews

The Lodge on Warner Hill

On your journey to our lodge, you will pass through a nostalgic covered bridge, drive by a babbling brook, and meander up a winding dead-end 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 less than 10 minutes from Berkshire East and the Deerfield River

30 Mar – 6 Apr

£501 per night

Guest favourite

Chalet in Richmond

4.98 out of 5 average rating, 86 reviews

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.

10–17 Sept

£465 per night

Guest favourite

Chalet in New Marlborough

4.92 out of 5 average rating, 50 reviews

Modern & Secluded on 40 Acres - Fast Wi-fi

Total privacy and beautiful mountain views, set on 40 acres, floor-to-ceiling windows, wrap-around deck with table, and chairs. You can't see any other houses and they can't see you. 20ish min to Butternut and Catamount Ski 10-15 min to Restaurants and Shops Great outdoor space. 2 large TVs with Direct TV, Netflix, Amazon. Wifi throughout. Whirlpool bath. On-property hiking trails. ***VIDEO (copy and paste) https://rb.gy/29we4t***

3–10 Dec

£523 per night