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Cozy Berkshires Cottage

Stay in a cozy Berkshires 1920's cottage! The bedroom occupies the entire second floor with peaceful views of the surrounding field and yard. The cottage is set back from the main road, easily accessible yet private. - Zoned air conditioning & heating makes every room comfortable year-round. - Close to Tanglewood, Jacob's Pillow, Outlet Mall, Kripalu, Turnpike. - Ideal for couples, solo adventurers, business travelers, and furry friends (pets). (Note: MA requires 11.7% tax added to charges)

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All-Season Berkshires Escape: Ski, Hike, Swim

Explore the best of the Berkshires, then retire to this charming 4-bed, 2-bath New Marlborough home to lounge, grill, dine, and lay your heads. The Konkapot River runs next to this vacation rental, which abuts protected land and a nature preserve. Within 5 miles of the home, you can access the Gedney Farm wedding venue, warm-weather attractions like Lake Garfield Beach and the Appalachian Trail at Beartown State Forest, winter hotspots like Butternut Ski Area, and renowned farm-to-table dining.

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Netherwood - North Adams Guest House with Views

Stay at Netherwood in a classic New England carriage house converted into a guest house with modern amenities, including king beds and en suite bathrooms. Private with amazing views, yet readily accessible to local attractions. Price includes 1 king bedroom suite and exclusive use of the lounge and kitchenette. You can use 2 more suites for another $100 each per stay (for stays up to 2 weeks). Indicate the number of suites you will need (1, 2, or 3); you'll be charged for add'l suites later.

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Bright Stockbridge country home, near everything!

Berkshires charm in this fully renovated 1800's post and beam farmhouse set on 5 park-like acres. Features open plan living/dining/kitchen with gas cooktop and gas 3 sided fireplace, lovely sun room, master suite downstairs and 2 br, bath and sitting area upstairs. Spacious deck overlooking the expansive property Conveniently located between the charming towns of Stockbridge, Lenox & Great Barrington. We are surrounded by 4 ski areas, the closest is 10 minutes away! Many dining options too.

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The Brook House at Race Brook Lodge

Cozy, private brookside bungalow sleeps four. Bright studio living space with queen and two twin beds, full kitchen, breakfast nook. Beyond the shady porch, enjoy rolling lawn, hammocks, abundant hiking. The Brook House is situated on the grounds of Race Brook Lodge, with breakfast, swimming pool, lawn games, and great hiking right on the property, including direct access to Race Brook Falls. Also just steps away from the Stagecoach Tavern Restaurant and Barnspace and DCSC performance spaces.

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Bucolic Berkshires House~Hiking Heaven

UNIQUE, bright, open space with a great kitchen and thoughtfully decorated. Near MANY exciting destinations such as skiing, cultural and arts destinations, vineyards, antiquing, you name it, in both the Berkshires and Hudson Valley. Located on an unpaved road and adjacent to a beautiful park and a nearby lake. There's so much to do, but if you'd prefer to take a more relaxed approach to your get-away then shop the wonderful local food stores and farms and enjoy cooking and our lovely house.

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Spacious contemporary w/ beautiful gardens!!

Beautiful, spacious, comfortable, light filled contemporary home, set on 5 acres, truly a nature lover’s delight. 3 large BR’s, all en-suite. AC throughout. Gourmet kitchen & open flr plan w/ great flow plus office and den. Private on 5 Acres, set back from road. Super convenient location. Award winning gardens w/Koi pond to delight the senses. 50" and 65” smart TV's, hi speed internet with 200 MBS. Hiking trails right from the back of the property. A special property!!

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2 Bed Berkshire Getaway @ Stephentown Hotel

Welcome to the historic Stephentown Hotel in the heart of the Berkshire & Taconic Mountains. Completely gut remodeled two bedroom apartment, brand new everything! Located on the 2nd FL. Large apartment, private arcade with (x3) real arcade games, private custom kitchen, soaking bathtub, bright and spacious with plenty of windows, ductless ACs, plus a Washer Dryer in-unit. Located minutes to Jiminy Peak! Outdoor area w/ fire pits, BBQ, picnic tables, outdoor games, etc.

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Willowbrook: A Sun Filled, Mid-century Modern Home

Welcome to Willowbrook! Our home is the perfect getaway from which to explore all that the Berkshires has to offer. This secluded yet close to town property has access to miles of hiking trails, ski resorts, and cultural institutions. Once home to members of the Crane family who have lived in Dalton since 1799, you can stay in a piece of history and even visit the Crane paper museum in town! We are so looking forward to hosting you in this beautiful place we call home.

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Whistler's Inn/The Garden Room (#9)

Whistler’s Inn is an 1870 English Tudor mansion in the heart of Lenox near Tanglewood, Shakespeare & Co., and all of the Berkshires’ most popular cultural venues. The home was once owned by Mr. and Mrs. Ross Wynans Whistler, railroad tycoon and nephew of the painter, James M. Whistler. Whistler’s Inn captures the warmth, comfort, and elegance of a bygone era. The inn has been featured on National T.V. - The Travel Channel and Fodor’s Bed and Breakfast Country Inns.

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Berkshires retreat in Great Barrington

Nearby cultural attractions include Tanglewood, Berkshire Theatre Group, Mahaiwe, Norman Rockwell Museum. 22 minutes to Jacobs Pillow. Near Hiking and area lakes in Great Barrington/Housatonic. We are on a country road only 4 miles to the town of Great Barrington, 5 Miles to West Stockbridge. Great spot for peaceful relaxation with gorgeous grounds and gardens; swimming pool in summer, fire pit on private patio. In winter, visit ski areas Butternut and Catamount!

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Serene Lenox Hills Cottage - Berkshires

Lenox Hills Cottage is a rustic two bedroom cottage located in the heart of the Berkshires, surrounded by stunning nature views. Tranquil and secluded, yet just minutes away from major attractions like Tanglewood, Kennedy Park, Kripalu, the Mount, Miraval, and downtown Lenox - home to many great restaurants. It's the perfect getaway from the city. No central air though remains fairly cool during the summer. Has cieling fans and portable fans.

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Berkshire Mountain Guesthouse-Near Jiminy Peak

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Historic Housatonic Guest House - near Tanglewood

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The Inn at Freeman Elms Farm B & B -Telly Room

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MtViews☆Gorgeous Meadowhurst Farm MoCA

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Beautiful Hartfield House in The Berkshires

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Iris Room bright with 4 windows :)

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Charming Victorian Farmhouse-Bedroom 2

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Spacious King BR in Lee

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Studio 208 at Garfield Annex on Main St

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comfy, cute flat with the river in my backyard

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A Sacred Place

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New Studio In Town, By the Water

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2 Bed Berkshire Getaway @ Stephentown Hotel

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queen size bed in a cozy fun riverside apartment

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Downtown | Waterfront | Walk to Shops

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Sheffield Lodge - Monument Room

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Granville House - Queen traditional

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Sheffield Lodge - Greylock Room

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Sheffield Lodge

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Berkshire Hospitality and Comfort

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Whistler's Inn/The Petite Chambre (#11)

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