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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.

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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!

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Secluded Cabin w/ PRIVATE HOT TUB and LAKE ACCESS

Festive season is here! And so is the opportunity to stay at an idyllic, secluded property near SKIING, the lake, and hiking! Welcome to the Cabin on Hillside, a peaceful retreat from the hustle and stresses of daily life. Situated in the charming lake town of Copake, you get all the fun of a quaint lakeside community, with the privacy of your own log cabin. After a day of fun, relax in your very own hot tub, swing in the hammock, or cozy up on the couch with some lemonade. Your oasis awaits!

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Tiny House on 70 Private Acres in Hudson Valley

Welcome to "The Tiny" at The Hemptons in Upstate New York! The not-so-tiny house is 400sf with plenty of space to stretch out. Each of the two bedroom lofts have a comfy queen bed on a low profile frame. The kitchen is equipped for basic cooking (read: Not good for Thanksgiving, but perfectly suited for standard cooking endeavors). Although we'd encourage you to check out many the local eateries (see below)! The bathroom is full size and likely bigger than the one in your first NYC apartment.

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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.

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Walk to Brewery in Historic Railroad Depot

This light-filled space is in a separate wing of my house with its own private entrance. There is one bedroom with a king-sized bed, spacious living room with table for meals, a large TV, a refrigerator/freezer stocked with bottled water and 1/2&1/2 for coffee, microwave and coffee maker with coffee pods are provided. You will hear the train as it travels through town. There are several places to eat nearby. Be sure to check out GUIDEBOOK on my listing to see what our area offers!!!

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Cozy Cottage Catamount, Berkshires Walk to Brewery

This cute, cozy cottage is located in the center of Hillsdale, NY on the grounds of the Second Empire landmark Mount Washington House, located in the hamlet’s National Historic District. The cottage is perfectly located between Hudson, NY and Great Barrington, MA and you can walk to stores, parks, Roe Jan Brewing Company, Taconic Ridge, the Harlem Valley Rail Trail and more. Very close to Catamount Mountain Resort, Copake Lake and Bash Bish Falls. Public EV charger located in west lot.

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Relaxing secluded stay with loving social animals.

Do you love nature, animals, and spa comforts? Then this is the perfect place for you! This is a fully finished, private area ground-floor walk-out, in the basement of the main house. Right outside your front door is 800 acres of hiking trails. You are surrounded by a mature forest, with loving and social goats, geese, ducks, kitty, and pups. To enhance this private retreat there are a hot tub and sauna steps from your door. Just Added mini split AC!

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Hudson Valley Hilltop Barn

A private hilltop oasis in nature. Newly renovated barn with some luxury amenities including sauna & outdoor firepit & movie theater screen & on a 15-acre hilltop with views & privacy in Hudson Valley / Berkshires. Fully stocked for cooking and tons of games. Perfect for winter sledding right on our hill. 100 acres of untouched nature around property. Near great shops & restaurants in Hudson & Great Barrington. *Pets must get written approval*

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Copake Retreat

Our cozy 3 bedroom home is 120 miles from New York City and 150 miles from Boston. It's located in a friendly private lakeside community with 2 sandy beaches on Robinson Pond. The surrounding area is gorgeous with rolling hills and farms. We're within a half-hour drive from Great Barrington, MA., Hudson, NY, and Millerton, NY. and it's a very short drive to Taconic State Park. Enjoy our 4-season Copake Retreat!

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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.

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Beautiful cottage at the foot of the Birkshires

Come stay with us in our beautiful cozy cottage, on a small lot located in the heart of Copake Falls, walking distance to Taconic State Park. Enjoy great farm to table dining, ski the Berkshires (just under 10 minutes to Catamount Resort), hike to Bash Bish Falls, bike the Harlem Valley Rail Trail, and swim in the spring fed iron ore pit during the open season.

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A sunny, quiet chalet beautifully decorated.

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Overnight at Althouse-Higgins

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

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Lakefront +views +skiing +bbq +firepit +games

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The Ancram A - Luxury Mid-Century Modern Cabin

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Cozy Creative Retreat in Converted 1856 Church

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Gorgeous Tiny House with Mountain View

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Columbia County Getaway - Raspberry Ridge Cottage

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