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Cabin in the woods w cedar Hot Tub + private pond

The Hemlock Hideaway is a charming, rustic cabin in the woods designed for rest and relaxation. Guests will journey into simpler times, inspired by antique furnishings that remind them to slow down and unwind during their stay. The cabin is isolated yet only 10 min drive to Jiminy Peak for skiing as well as park and trails for hiking, apple orchards, excellent restaurants and foliage viewings. Cherry Plain State Park, Mount Greylock, Lebanon Speedway, Albany, and Pittsfield are all 25 min max.

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R3Bliss - Estate with Hot Tub, Tennis Court & Pool

Private estate in the Berkshires with 13 acres, 4 bedrooms, private pool + salt water hot tub (all year) indoor + outdoor fire pits, and sunset mountain views. Perfect for larger family vacations, group trips and special occasions. Located in the Berkshires, you'll be close to outdoor adventures, hiking trails (Mt Greylock) and art, theater, dance, music, film, and history. Kayak or swim at the local lake. - By the Jiminy Peak Bosquet ski resorts - 15 mins from Tanglewood and Jacobs Pillow.

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Berkshire Getaway Ranch 3 acres + saltwater pool

Escape to the Berkshires in my newly renovated home sitting on 3 acres of land with in-ground saltwater pool. Enjoy the private, rural feel at this property with picturesque sunsets on the hills beyond. Under 5 min to Onota & Pontoosuc lakes, 15 min to Jiminy Peak & Bousquet ski resorts & a short drive to Lenox/Williamstown/North Adams. Light a fire in the living room or master bed & enjoy the cozy ambiance of the vaulted wood ceilings & large picture windows framing views of the bucolic hills.

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The Catamount Haus w. Pool/Hot Tub

Welcome to the Berkshires! Located almost across the street from the Catamount Ski Resort - come unwind with some fun, peace and adventure. This 4 bedroom 4 bath sits on a 5 acre property nestled amongst the trees with a private pool, hot tub and Mountain View ’s to gaze at. Dine at the quaint, hip restaurant in little cat lodge next to the ski resort, have coffee in Hillsdale at Cook& Larder. Or check out the shops in Great Barrington. There is a ton to do in the Berkshires all year long!

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Palatial, central Berkshire, large family home

Welcome to The Manor - your escape to the beautiful and serene Berkshires. You will enjoy the perfect retreat away from the hustle and bustle with this spacious and well decorated 5-bedroom house featuring a pool, quiet surroundings, and easy access to nearby attractions like Tanglewood, Mass MoCA, The Norman Rockwell Museum, ski resorts and world class restaurants. Perfect for families and friends looking to get away and spend quality time with each other. We look forward to seeing you!

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Cozy Condo @ Jiminy Peak

Nestled in the majestic Berkshire mountains, this Cozy Condo is a home away from home! It features 2 bedrooms with closets & dresser space. The master bedroom connects to a full bathroom and has a TV for when it's time to unwind in the comfort of bed! The fully equipped kitchen/dining area opens into a spacious living room. It's the perfect place for evening gatherings with friends or a romantic night in front of the fireplace! Free access to 2 heated pools, hot tubs, sauna & fitness center.

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Stylish Rural Sanctuary

Recently re-opened for short term stays! Just minutes from Chatham, NY, and nestled in the heart of the Hudson Valley, this serene home on over 8 acres offers breathtaking mountain views. Impeccably renovated in 2022, it seamlessly blends the charm of 18th-century Shaker architecture with the sleek elegance of modern Scandinavian design. Indulge in lightning-fast fiber internet, large smart TV, top-tier appliances, including a Miele fridge, Bertazzoni stove, Bosch dishwasher, and more!

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House in beautiful Berkshires

Welcome to our home in the beautiful Berkshires! Enjoy this clean, private upstairs of a split-level ranch house. We are just 10-min from downtown Great Barrington and in a wonderful location for exploring. We live downstairs- myself, a 7 year old boy and medium-sized dog. You may hear us :-) In the summer you may see us on occasion with friends and family in the saltwater pool. We’re happy to meet you and also happy to give you space- it’s your call. Wishing you a wonderful trip :)

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Berkshire Mountain House

Bring the whole family to this beautiful home in the woods, just minutes from Mt Greylock hiking, Jiminy Peak skiing, local farms and activities. There's truly something for everyone. Go for pumpkin picking and hayrides at Whitney's Farm or walk/bike Ashuwillticook Rail Trail. We are 10 minutes to Pittsfield and 15 minutes to Williamstown. Or have a great time never even leaving the house, while grilling outside, watching movies in the home theater, or cooking in a chef's kitchen.

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Idyllic Berkshires Getaway

Secluded large ranch in the country on 8 acres with pastoral scenic views, only 7 minutes drive from the center of Great Barrington and Lake Mansfield Beach, 10 minutes to Ski Butternut, 12 minutes to Stockbridge, 20 minutes to Lenox and Tanglewood . Kids playroom and a spectacular jungle gym, perfect for entertaining inside by the fire or outside on the patio with the bbq with beautiful views surrounded by pine trees. Perfect for fall foliage, skiing, spring and summer!

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Perfect Base for Your Berkshire Adventure

Charming private cottage with shared pool use. This newly renovated garden studio features high ceilings, a separate kitchenette with granite counters, mini fridge, microwave, queen sized bed, and rustic Arts & Crafts furniture. Located in a separate outbuilding, the cottage is close to woodland hikes, excellent biking, as well as many other attractions in the Berkshires. The beautiful in-ground pool is perfect for an afternoon dip - guest hours are usually between 3-5.

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Hollywood Bungalow in the Berkshires

Cool Cozy Rustic Country Bungalow with Screening Room on filmmakers/artists' enclave that's well-located in clean and beautiful Williamstown, near incredible Hiking Trails, Farms, Skiing, MASS MoCA, Clark Art Institute, Williams College, with Pool access, Cable & Smart TV, Porch and Patio, Grill, Fire Pit, Piano Bar Outbuilding with stereo & its own WIFI, First Floor Bathroom with Jacuzzi Bathtub, Laundry, fast WIFI, and lots of outlets in a quiet area on a quiet street.

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Berkshires Oasis Retreat: Art Meets Nature

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Berkshire Lakeside Retreat

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Bougie B’s Mountainside Getaway

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Berkshire Lake House, gunite pool, Chef's Kitchen

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10 Acre Country Estate with Pool, Hot Tub & Views!

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Hilltop: Panoramic Views w/ Pool near Catamount

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Berkshire County modern home + pool

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Private & Stylish Berkshires House for All Seasons

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Condo Resort at Jiminy Peak Ski Mountain's Base

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Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base

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Unique - Country suite @ Jiminy Peak

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Jiminy Peak Country Inn 1 Bedroom Suite

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Ski-in/Ski-Out on Jiminy Peak

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