Chalet holiday rentals in Massachusetts

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Top-rated chalet rentals in Massachusetts

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Chalet in Truro

5 out of 5 average rating, 3 reviews

Magical Round Cottage Home

You'll love this unique and romantic escape. Nestled in the majestic woods of South Truro and just minutes to some the most beautiful beaches in the world. My home is truly a gem💎 Greats for writers and artists, remote work, and anyone who needs respite from the hustle and bustle of the world. Perfectly surrounded by national seashore on 3 sides. Hiking, biking and beaches within minutes. A wonderful place to see the northern lights nowadays and a lovely spot to vacation anytime of the year.

Guest favourite

Chalet in Otis

4.95 out of 5 average rating, 414 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

Superhost

Chalet in Great Barrington

4.96 out of 5 average rating, 70 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.

Top Guest favourite

Chalet in Charlemont

4.99 out of 5 average rating, 71 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.

Top Guest favourite

Chalet in Orange

5 out of 5 average rating, 27 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

Superhost

Chalet in Lenox

4.82 out of 5 average rating, 22 reviews

Peaceful Chalet in the Woods: Walk to Lenox

Family friendly, spacious cabin. Tons of natural light a wood stove and private garden. Woodsy feeling in contemporary setting next to Kennedy Park. Downstairs is mobility friendly w/ 1 twin ensuite, 1 Queen w/ separate full bath & TV room. Upstairs: Main bedroom with w/separate full bath and sitting area. Lovely deck, stunning views. Ping pong table and plenty of games for kids! 10 mins drive to Tanglewood, Kripalu; 8 min drive to Bousquet Ski Mtn., 15 to Red Lion & 25 to Butternut Mtn.

Top Guest favourite

Chalet in Monterey

4.98 out of 5 average rating, 83 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 Charlemont

4.99 out of 5 average rating, 101 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

Guest favourite

Chalet in Otis

4.91 out of 5 average rating, 64 reviews

Kayaks, Sauna & Family: Relax & Play

Join our unique Berkshire vacation experience, away from the hustle and bustle: 🌟Kayak & swim on the lake 🌟Boost wellness in our barrel Sauna 🌟Relax around the gas grill, pizza oven & firepit 🌟Minutes to restaurants & hiking 🌟Entertainment 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 (Fast Wifi) 👉arcade-style games and more

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.

Guest favourite

Chalet in Richmond

4.97 out of 5 average rating, 93 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.