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The Old Red Barn

Renovated studio in barn built circa 1830, centrally located to all activities in the Berkshires. Bright and sunny space with views of fields and spectacular sunsets. Open upstairs loft bedroom with pine floors, catherial ceiling, exposed beams, full kitchen , bathroom and washer and dryer. The Berkshires are beautiful in the fall , come stay ! 5 minute drive to town. Walk to the Green River , hike the trails. We provide all basic household supplies. We invite all to enjoy our old red barn.

May 26 – Jun 2

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Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!

Sep 13 – 20

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Hideaway with Spectacular Berkshire Views

Located on the border of Massachusetts and Connecticut with spectacular views of the Berkshire Hills and fifteen minutes drive from Great Barrington, MA, this apartment is located on a secluded seven-acre property. Owners live on the property. Above an artist studio this renovated one bedroom apartment with private entrance, full kitchen, fast internet is stylish, light and airy with a contemporary and eclectic decor. Please note During winter all-wheel drive vehicle is strongly advised.

Nov 27 – Dec 4

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COZY GUESTHOUSE MINUTES AWAY FROM HIKING!

Renovated 1880's one bedroom cozy guesthouse in beautiful Southfield, MA. Full kitchen stocked with all necessities. Comfortable & stylish with a luxury king size bed. Minutes away from Ski Butternut, Berkshire attractions & trails. Walking distance to breakfast and lunch at The Southfield Store or have dinner at nearby The Old Inn On The Green and Cantina 229. 10 minutes from Great Barrington. Enjoy leaf-peeping, hiking, waterfalls, apple picking, skiing, and much more!

Oct 3 – 10

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Perfect Berkshire getaway.Cozy cottage.Great wifi.

Family-friendly rustic modern getaway set on 4 acres in the beautiful Berkshires. Escape the city and work using our fiber internet, or just come relax and read a book by the fire. Spend time in the great outdoors skiing at Butternut, hiking at Bob's Way or taking in a cultural event at Tanglewood or Jacobs Pillow. 15 minutes to Great Barrington, Lee and Lenox. 5 minutes to Otis Ridge ski, 15 minutes to Butternut and 25 to Catamount there is always something to do.

Sep 28 – Oct 5

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The Granary at House on Golden Hill

The Granary is a 1735 carriage house situated on a historic Berkshires farmhouse compound. Featuring 20-foot cedar-lined ceilings, original wide-planked pine floor boards, and large windows and skylights, the Granary provides sweeping mountain views and an idyllic Berkshires experience. King-sized bedroom, eat-in kitchen, and bathroom with soaking tub and standing shower. Minutes to downtown Lenox, Tanglewood, and centrally located in the Berkshires.

Oct 26 – Nov 2

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Jaw dropping mountain & lake views

Curl up with a good book by the fire and gaze out at the dreamy picturesque mountain and lake views..... Or ski, swim, hike and enjoy so much more that the Berkshires has to offer in this centrally located Southern Berkshire county home. Private mountain top adventure awaits.. Centrally located in Southern Berkshire County: 10 minutes from Butternut ski, 20 minutes to Great Barrington, 25 minutes Stockbridge & Lenox and 2 ½ hours from NYC and Boston.

Feb 5 – 12

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Modern studio with views of the treetops

Our Stockbridge studio is located at the heart of the Berkshires, just north of the center of town. It is a brand new, modern, second floor studio suitable for up to four adults with views of the surrounding woods, a large kitchenette and comfortable, spacious living space for relaxing in your home away from home. There is a full bath and a private entrance. It is perfect for a weekend getaway or a seasonal stay, whatever your heart desires.

Oct 14 – 21

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Rustic-Modern Studio - Near Hudson, Chatham, & GB

Get a small rustic-modern cabin feel in this cozy and self-sufficient space. 10 minutes from Chatham, 15-20 minutes from Great Barrington, Lee, Lenox, Kripalu Center for Yoga & Health, Catamount Ski Resort, TangleWood Institute and seconds away from a beautiful hike up Harvey Mountain in Austerlitz, NY. The wood-stove will keep you warm in the winter months and the large field and creek in the backyard will relax you in the summer.

Oct 23 – 30

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Private Berkshire Barn Apartment

A private entrance and apartment all to yourself. You are within a 2 minute drive of downtown Sheffield or a 10-15 minute walk. Also within a short drive of superb restaurants and local ski areas, Great Barrington, Tanglewood, Jacobs Pillow, The Rockwell Museum and numerous other Berkshire attractions. Also within a short drive of Berkshire, Salisbury, Hotchkiss and Simon's Rock schools.

Nov 4 – 11

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Home in Great Barrington. Steps from downtown!

Central and Private! Just steps away from historic downtown Great Barrington and East Mountain Hiking trails. Enjoy sunset views with friends and family, before you walk into town for a night out! 10 minutes (2 miles) to Butternut Ski Area This brand new home features all new appliances and furniture. Enjoy luxury, charm, and privacy while you rest easy at The Maple.

Jan 11 – 18

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Newly built cottage on working farm

This light-filled, spacious, newly built, one bedroom cottage sits atop a knoll with full view of a working vegetable farm. Located on a quiet road, you will enjoy a comfortable space adorned with modern features. We are 4 minutes to Catamount ski area, 10 minutes to Great Barrington, and near all the Berkshires has to offer.

Feb 5 – 12

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Modern Farm House 5 minutes from Great Barrington

Apr 8 – 15

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A sunny, quiet chalet beautifully decorated.

Mar 20 – 27

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Berkshire Mountain retreat with Urban eco-luxuries

Apr 29 – May 6

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Cozy Berkshires Cottage

Sep 29 – Oct 6

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The old sawmill from 1771

Nov 20 – 27

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The Hideaway: Berkshire Home - village of Egremont

Sep 21 – 28

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Wow! Best BERKSHIRE SnowHome #1 Private SuperClean

Oct 10 – 17

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Elegant Year-Round Lakeside Retreat with AC

Nov 17 – 24

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Secluded but not isolated Berkshire Retreat

Oct 24 – 31

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Cozy Berkshire Cottage Style Apartment

Apr 21 – 28

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Station House 1E Private Room & Bath

Aug 26 – Sep 2

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Sunny Berkshire Studio Apartment

Jun 14 – 21

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Serene Suite Catamount Berkshires Walk to Brewery

May 18 – 25

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Bike Path Hideaway Near Smith, Cooley, Northampton

Sep 1 – 8

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The Beer Diviner Brewery Apartment

Oct 12 – 19

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Sunny, light filled loft in 1873 Colonial

Dec 21 – 28

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Cozy Mountain hideaway Windham, Hunter

Sep 19 – 26

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*Great Reviews* Hunter Mtn. Clean/Close/Cozy Condo

May 29 – Jun 5

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Stylish Condo Ski on/ Ski off Hunter Mountain

Jun 25 – 30

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Harmony Valley Home, bright & inviting 2-BR escape

Nov 8 – 15

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Spacious and stylish entire one bedroom apartment.

Jul 1 – 8

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Downtown Flat Iron Condo - walk to MoCA #12

May 7 – 14

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Elegant, spacious studio apt in historic mansion

Nov 16 – 23

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Hunter Mtn Liftside Ski In/Out, Slopeside!

Oct 17 – 24

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select.subtitle used in hero area to show the listing's privacy, property type and city one two three four five six seven eight nine ten eleven twelve thirteen fourteen fifteen

select.subtitle used in hero area to show the listing's privacy, property type and city one two three four five six seven eight nine ten eleven twelve thirteen fourteen fifteen

select.subtitle used in hero area to show the listing's privacy, property type and city one two three four five six seven eight nine ten eleven twelve thirteen fourteen fifteen

select.subtitle used in hero area to show the listing's privacy, property type and city one two three four five six seven eight nine ten eleven twelve thirteen fourteen fifteen

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