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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

Comfortable Berkshires retreat on mtn resort, SISO

Once a retreat for an NYC real estate family, this grand yet comfortable place in Jiminy Peak has retained the feel of a chalet: perfect after a ski/hike/bike through the beautiful mountains around it. 4 bdrs allow your group to space out, and a great room with 20 foot high ceilings extends through the dining area. Convenient to many Berkshires spots (Tanglewood, museums, etc.), a 2nd living room, fireplace, jacuzzi, and access to slopes, hot tubs, heated pool & gym complete the perfect getaway.

Barn Stay at Shadowbrook Farm

Welcome to the Shadowbrook Farm Stay. Tucked in the hills of upstate New York, this 1700's Shaker barn has been restored into a beautiful guest house. It sits upon a two hundred acre working pasture raised meat farm. This barn was used to hold, and milk cows for two hundred and fifty years. Guests will have access to portions of the farm lands which are highlighted on the maps provided in the Farm Stay manual. If you follow the farm road, you are able to meet every farm animal on the property!

Historic Stone Church in The Berkshires

<b>Hinterland Hall</b> was built in 1836 by the Saint Luke's Episcopal Parish and joined the National Register of Historic Places in 1972. Ripe with history and impeccable beauty, Ian & Jane purchased the old stone church in May of 2021, completing an extensive restoration process in accordance with the Massachusetts Historical Commission. It is with great pleasure that we open our doors to you for a wondrous stay. <b>Follow us @hinterlandhall</b> Please inquire about weddings & events.

1 Bedroom; 1.5 miles to Jiminy Peak; Pet Friendly

Our country suite is nestled on the 2nd floor of the horse barn of our gentleman farm. It features a one bedroom with a queen bed, open concept living room & full kitchen, a large bathroom with washer & dryer, spacious entry and a large deck. A queen sleeper sofa with mattress pad allows for an additional two guests. With Jiminy Peak Mountain Resort the backdrop at 1.5 miles away, it is perfect for a weekend getaway or lengthy vacation should the numerous area attractions keep you here longer.

Cozy apartment near Jiminy Peak

Two cozy bedrooms with an efficient kitchen make this a great weekend getaway for 2 adults or family of 3 to use as a base to explore both north and south Berkshire county in every season. About a mile from Jiminy Peak Ski Resort, less than 5 minutes to Bloom Meadows, 15 minutes to both Williamstown and Pittsfield, and 30 minutes to Mass MoCA, the quiet, wooded mountainside surroundings let you enjoy nature at its finest while easily getting to the area's many cultural attractions.

Beautiful Jiminy Peak Townhome Family Friendly

Leave the city behind and come work remotely from our 3 bedroom, 2 bathroom newly renovated townhome. Whether you're visiting the Berkshires area in the winter for skiing at Jiminy Peak, or you're seeking summertime adventures on the lakes and the hiking trails, this 3 level home with puts you right in the middle of the action. Perfect for families, this rental is located in a community just a mile (3 minute drive) from the mountain and managed by Moresi Property Management.

Corey Road Condo | @ Jiminy Peak • Pool • Hot Tub

Escape to our updated 2-bedroom, 2-bath condo at Jiminy Peak! Perfectly situated for the ski season, you'll enjoy quick access to both the slopes and apres ski. After a day on the trails, unwind at nearby restaurants like Christianson's Tavern or Bluebird & Co, offering top notch local eats. Bougie B's features updated amenities and that perfect touch of class to make you feel special. Come experience the beauty of the mountains today—your perfect escape awaits!

Jiminy Peak Slopeside Getaway • Ski & Adventure

Jiminy Peak Slopeside Getaway • Ski & Adventure ★☆ ABOUT THIS SPACE ☆★ Welcome to Jiminy Peak Slopeside Getaway, your all-season mountain retreat. Enjoy scenic views and a true ski-in/ski-out experience—just a 3-minute walk to the chair lift at Jiminy Peak. This 2-bedroom, 2-bath home sleeps up to 7 guests and offers private parking, a porch, and a deck, plus access to a heated pool, indoor/outdoor hot tub, and clubhouse.

Jiminy Peak Country Inn - ski in/out condo MT view

Rent your very own condo in the Country Inn at Jiminy Peak Mountain Resort.This unit is just steps away from the entrance and your ski locker. Ski in/out and never have to move your car! Spectacular view of the mountain from your windows, close to all the amenities the resort has to offer. The resort offers a year-round heated pool, 2 hot tubs, a gym, fireplace lounge and restaurants. The perfect mountain escape.

Mountainside Condo Ski on/off

Recently Renovated!! Nestled in the Berkshires, a getaway to Jiminy Peak offers everything you need, so close to home. Just a short walk back to your vacation home to relax before heading to dinner at one of our on site restaurants. Jiminy offers all that you need in a resort experience – lodging, dining, shopping and an array of activities and entertainment.

Rustic Cabin | Barrel Sauna | Private Pond

The Hemlock Hideaway is a freshly renovated, charming cabin tucked into 14 acres of quiet woodland in the Berkshire foothills, built for the kind of rest that's hard to find anywhere else. This is a genuine rustic escape: complete with antique furnishings, a wood-burning stove, mid-century stove, no television, and the sound of nature just outside your door.