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Mountain Serenity 20 Acres, Hot Tub, Jiminy<10min

Private Berkshires 20Acre estate designed by acclaimed architect and author Norton Juster. An exclusive 4 bedroom retreat, with mountain views from every room, cathedral ceilings, cozy fireplaces, elegant living spaces, and outdoor fire pit, it’s the perfect place to unwind. Relax in the hot tub or sauna after a day of skiing at Jiminy Peak or Bousquet. Newly renovated with high end furnishings and chef's kitchen. A perfect mix of adventure and tranquility awaits—book your mountain escape today!

Red Rock Summit: Pool | Privacy + Views | Sauna

Welcome to Red Rock Summit, where an award-winning architect-designed home takes advantage of majestic views at every turn. This contemporary 4-bedroom, 4-bathroom home on 80 impressive acres is just 2.5-hrs from NYC & Boston. Enjoy the bright and airy interiors and abundant outdoor amenities, including a large pool, sauna, serene swimmable pond, and firepit. Explore nearby villages for shopping and dining, or hit the slopes at Catamount Ski Area. Welcome to a mountain retreat like no other.

Sauna + Hot Tub Escape | Private & Pet Friendly

Relax with the whole family or escape with your partner for a romantic getaway to Lovers Lane. Surrounded by trees and set against the backdrop of Monument Mountain, you'll have everything you need in this quiet, private setting to fully enjoy some time away. It's a short drive to downtown Great Barrington & Stockbridge where you will find cute shops & great dining. Ski at Butternut, see live music at Tanglewood or hike Monument Mountain. Good times await at Lovers Lane in the Berkshires.

Scandinavian-Style Luxury Barn Retreat

**Summertime access to nearby Queechy Lake beach!** **Outdoor sauna coming for Summer!** Exceptionally private getaway on 8 beautiful acres near Chatham, NY, this historic barn has been meticulously renovated, including a full chef’s kitchen. One of the area’s most stunning accommodations, ideally located between picturesque destinations— the Berkshires, Great Barrington, Taconic State Park, Beebe State Forest, Ooms Conservation Area, Tanglewood, Hudson, Kinderhook, and so much more!

Berkshire Mountain home views, pool, Queechy Lake

Note: pricing includes all fees such as cleaning and air bnb services charges! Happy to break it down for you before booking. Serene house on 11 acres, surrounded by farmland. Perfect for families to share! Enjoy beautiful view of Berkshire mountains while sitting on expansive deck or in bright,sunny screened-in sunroom. Heated, 20x40 inground salt water pool. Membership to Queechy Lake included! Walk to Corkscrew Rail trail, 5 miles of flat, wooded trail for walking and biking.

Relaxing Mountaintop Retreat

Sitting atop the former Chickley Alps, this magical home is nestled between a XC Ski resort and conservation land. The many decks overlook the 50 acre property, which piqued the interest of acclaimed children's author, Eric Carle to build an inspiring retreat in the 1970s. Gather in the studio, where you may find some remnants of his artistic process splattered around the room. With 4 bedrooms, 2.5 baths, a workspace, and 3 distinct gathering spaces, there is room for all.

Bedroom Forest View I Sauna I Fire-pit I Trails

Escape to a secluded custom built tiny house nestled amongst old pines and the Umpachene River. Inside, rustic charm meets modern comfort with 2 lux queen-sized beds, a well-equipped kitchen and bathroom, a massive bedroom forest view and a private sauna. Outside the home you can find a cozy fire-pit, trails that lead down to the river, and a dining table for all your meals. Go out for a day of hiking and exploring, and come back to unwind to sounds of nature.

Elegant Mountain View Retreat By Evergreen Home

Evergreen Home Vacation Rentals invites you to this private country retreat, a recently renovated 1840 Schoolhouse. Just 7 minutes to Jiminy Peak and walking distance to Bloom Meadows, this stylish home features 360-degree mountain views, an in-home sauna, and a modern kitchen. Perfectly located near Williams College and world-class museums, you can enjoy hiking, cycling, and cross-country trails right from your door. Experience historic charm and modern comfort.

Berkshire Beauty + 6 BR/38 Acres mins from Jiminy

38 beautiful, private acres of Berkshire woods, cleared land, and mountain scenery. 6 comfortable bedrooms and 4.5 bathrooms. 9 Minutes from Jiminy Peak Ski Resort. 5 Mins from The Lake House cottages. Warm and cozy, modern gem. 4 Fireplaces, multiple hang out areas, napping areas, sauna, outdoor fire pit, views in every direction, two fridges, high speed internet, plus a kid cave in the basement. Perfect for all four seasons.

Misty Pines Cabin | Wood Stove • Sauna

Welcome to Misty Mountain Camp — a cozy 3-bedroom, 3-bath escape surrounded by peaceful woods and Berkshire charm. Enjoy nearby adventures at Beartown State Forest, Lake Garfield, Steadman Pond, and Greene Park, or explore local history at the Bidwell House Museum. After a day outdoors, relax on the deck, unwind by the fire pit, and soak in the quiet beauty of nature. The perfect getaway for families, friends, and nature lovers alike.

Steps to MoCA: 2bd + SAUNA!

A large, private 2-bedroom apt at the Small Mansion of Chase Hill Estate. Outdoor Sauna! Just a 5 minute-walk to MASS MoCA & downtown restaurants, 10 mins drive to Williams College & Clark. Whimsically restored (fast Wi-Fi & great water pressure!) and part of @chasehillartistretreat ✨ Your stay supports pro bono residencies for refugee & immigrant artists. Additional dates available beyond what the calendar shows—contact us!

Luxury Berkshires | Walk to Williams | Steam Sauna

Enjoy this private, design-forward guesthouse with a steam sauna, shower room, cathedral ceilings, and a Ritz-Carlton bed—set two blocks from Williams College and minutes from the Clark Art Institute and MASS MoCA. This is a smaller space, designed for luxury stays —more in line with a boutique hotel suite than a typical Airbnb. Featured in Insider Home, MSN Home, and the How to Decorate Podcast.