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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!

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.

Walk to Williams | Steam Sauna | Heated Floors

Winter Wellness Escape in the Berkshires | Treat yourself to a cozy, luxury retreat in the heart of the Berkshires—your private spa sanctuary with a steam sauna, radiant heated floors, and the iconic Ritz-Carlton bed. Perfect for romantic getaways, creative recharge trips, or restorative winter weekends. Welcome to Mt. Williams Retreat, a designer guest cottage just two blocks from Williams. Featured in Insider Home, this refined escape blends wellness, design, and comfort in every detail.

House Among Trees - A Perfect Holiday Getaway

The House Among Trees is a tranquil property in the Berkshires. This mid-century 3-bedroom home is equipped with all amenities to offer a truly relaxing stay. During the colder half of the year, enjoy winter sports nearby and then step into your own private Sauna to decompress. Enjoy amazing restaurants, antique shops, hiking trails. Visit Tanglewood, Jacob's Pillow, Hancock Shaker Village and other cultural centers. We'll be happy to provide recommendations based on your interest.

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.

Sleek Butternut Ski Chalet Lakefront HotTub Sauna

Newly Renovated Berkshires chalet with HOT TUB & Sauna, Pet friendly, 5BR 4 full bath on Lake Garfield 5 min to Ski Butternut, 15 min to Ski Catamount, 15 min Great Barrington dining /shops. Spacious, family-friendly home sleeps 14 with 2 living rooms, out door hot tub for 6, indoor infrared sauna, wood fireplace, BBQ, Solo fire pit sitting 6, fenced yard, decks, and 2 kayaks. Short walk to lake beach. Perfect for ski trips, lake stays, and group and family getaways.

See MoCA from your mansion+Sauna!

Large bi-level 4 bedroom apartment tucked away on a hilltop oasis above Mass MoCA (3 mins by foot). 10 mins drive to Williams College & Clark. Whimsically restored (fast Wi-Fi & great water pressure). Fully private with no shared spaces + outdoor Sauna! Your stay’s proceeds allow us to host refugee/immigrant musicians pro bono year-round at @chasehillartistretreat Note: more dates are often available beyond what the calendar shows. Please don’t hesitate to inquire!

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.

Woodland 5-BR Retreat 5-Min to Jiminy Peak

Nestled in the Berkshires, this 5-BR family home combines comfort and tranquility. The open floor plan connects living areas, and the private backyard has a brand new pool! Bedrooms are spacious, featuring ample natural light. Surrounded by beauty, this home offers a perfect blend of modern living and natural serenity. Home includes a foosball table, and swimming pool. Attractions at Jiminy Peak (5-min away), Mt. Greylock (17-min away), and Ramblewild (5-min away).

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.

Berkshires Escape + 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.