Chalet holiday rentals in Western Massachusetts

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

Peaceful VT Chalet w/ Mountain View’s

My peaceful 3-bedroom chalet has everything you need for your VT trip. The house comes with a washer, dryer, Roku TV’s, pullout queen couch. 2.5 bathrooms, indoor elec. fireplace, outdoor fire pit and fully equipped kitchen.Short driving distance to several popular golf courses, shops, restaurants, breweries, fishing, white water rafting, hiking, kayaking, ATV/snowmobile trails, & mountain slopes. An ideal base to explore the Green Moutain National Forests (VT) or the Berkshire Mountains (MA).

Chalet Sonsie: A Sweetwater Stay

Chalet Sonsie is a freshly-renovated waterfront getaway, where you can enjoy breathtaking views of Forest Lake year-round, from every room and all 3 levels of decks! Whether you're traveling with the kids, friends, or just looking for a quiet fishing retreat, there's something here for everyone. This cozy 2-bedroom home features 2 full kitchens, 1.5 baths, expansive fireplace and TV, plus a game room complete with foosball and mini-arcade! Book today, or check out other Sweetwater Stays! -Patti

The Mountain A-Frame at Mount Snow

Entire chalet-style A-Frame in Mount Snow with mountain views. Less than 1 mile from the base of Mount Snow and close to all the fun in the Green Mountains: AT access, swimming holes, covered bridges and more! Across the street you can hop on the Moover shuttle that takes you right to the mountain! 2 minute walk to market, coffee shop and local bar. 2 bedrooms + 1 loft, 1 bath, wrap around deck, cooking necessities, Smart TV and WiFi. You can find us on social (tag us!) @themountainaframe

Mountain Chalet mins from Mt Snow Skiing/hiking

Experience nature at this peaceful mountain retreat. World class skiing at Mt Snow is just 14 minutes away. After a day of outdoor activities enjoy a relaxing time in front of the fireplace. This cozy chalet boasts exposed wood beams and wood paneling all throughout the house. You will wake up in the master bedroom with views of the woods. During the off winter months, enjoy your morning coffee on patio with views of the mountain. The kitchen is well equipped with your cooking needs.

Mountain Chalet: Private Brook - Hot Tub - Firepit

The Brook House Vermont is set back in the trees and unbelievably cozy. It's a place to reconnect while listening to the brook. To enjoy big meals, conversations, and games by the fireplace. To bask in the sun or do yoga on the deck, or gaze into dark, starry skies from the hot tub and fire pit at night. There's skiing mins away at Mount Snow, swimming at Harriman Reservoir, as well as hiking, golf, mountain biking, antiquing, breweries, and some of the best food VT has to offer.

Highland Haus AFrame Lake Access Vintage 70s Charm

Authentic 1975 A-frame chalet nestled in peaceful Stoddard countryside. This cozy cabin sleeps 5 with two wood stoves and full kitchen. Perfect rural retreat just 2 hours from Boston! Explore nearby hiking trails, swimming spots, and fishing areas. Summer bonus: complimentary canoe access! Highland Haus offers a tranquil escape with vintage charm. Note for winter visitors: Shedd Hill Road requires AWD/4WD due to steep terrain. Your cozy retro hideaway awaits!

Catskill Chalet: Hunter Mtn Hideaway w/Hot Tub

Camp Van Winkle is a place to relax, unwind & reclaim your sense of calm. 🌳 Escape to our cozy Catskills chalet, the perfect base for your iconic mountain getaway! 🏡 Relax and unwind in our charming home, featuring a spacious deck with a bubbling hot tub, perfect for stargazing after a day of adventure. 💫 We are lucky to be surrounded by some of the most spectacular hiking trials and waterfalls in the Catskills, we dare you not to fall in love! 😻

Cozy & Bright Chalet near Mt Snow ◌ over the moon

A brand-new wrap-around cedar deck is complete and ready for you to enjoy! Our cozy and bright chalet is waiting for you. Come enjoy the outdoors however you'd like. Walking distance to a restaurant and market, and the Moover shuttle stop is just a stone's throw away -- skip the Mount Snow parking lot! Our chalet is close enough to what you need yet far enough away to offer you some peace and quiet.