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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

Dec 8 – 15

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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 23 – 30

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Country Cabin

Lovely private country setting. Listen to owls and coyotes at night, birds during the day. When it rains you can enjoy the sound on the metal roof. I only accept advance reservations of 2 nights or more. (You may reserve a single night booking within 5 days of the request.) The space is for 2 adults but I allow for flexibility, so don't hesitate to ask. Seasonal/weekend rates may apply. I live on the property with my partner and the cabin would not otherwise be on the real estate market.

Dec 21 – 28

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Sunny Riverside Apartment

The Berkshires are a perfect spot for a getaway week or weekend. You will enjoy this cozy 2-story apartment, easily accessible to all that the region has to offer. The apartment has a fully equipped kitchen, dining space, living area, and two bedrooms, overlooking the Housatonic River. Every town in South County is 5-15 minutes drive, and in 50 minutes you could be at The Clark Museum or Mass MOCA in North County. Several ski areas are nearby, and Kripalu is just an easy 10 minute drive.

Mar 22 – 29

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Riverfront Getaway

Our place is on a gentle flowing river, close to waterfalls, walks and the Berkshire cultural sites like Tanglewood and Jacobs Pillow . You’ll love our place because of the river, the deck, the hot tub; complete tranquility and a home away from home. Close to some great sites and activities, far enough away to escape. Our place is good for couples, friends and solo adventurers. Snowboarders/Skiers (or snow bunnies) and families can have great fun too! Sit back, relax and enjoy our home!

Sep 6 – 13

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Guest Suite in Old Chatham Hunt Country

Looking for all the perks of a hotel while staying at a house in the country? This tranquil, light filled room overlooks horse pastures and a dirt road in the heart of Old Chatham hunt country. A private entrance leads to a guest suite which includes a queen size bed, sitting area, kitchenette, and walk-in closet. Located on the first floor of a newly built, net-zero home. Power comes from solar and solar water panels provide for guilt-free hot showers! 50 MBPS fiber optic Internet!

Oct 4 – 11

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Sunny, light filled loft in 1873 Colonial

Relax in our bright, very spacious, and quiet loft, on six open acres. Lounge on the stone terrace, under the stars, by a cozy fire, near the garden. 35 min to Northampton, 35 min to MassMoca, 10 min to Berk. East. Pellet stove, Fiber Optic Wi-Fi, streaming options, and cell coverage. Fully outfitted kitchen with home made granola, and assorted beverages. Two hybrid bikes available for use. There are 3, 5-ft long skylights, and a cathedral ceiling= much natural light!

Mar 5 – 12

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Lenox - Walk to Town - Berkshire Home

Come, enjoy the Berkshires! This cottage built in the 1950's has recently been completely renovated from stem to stern to bring it up to date with the most current design standards. It is a 2-bedroom, 1-bathroom space with a large front yard and beautiful backyard for grilling. Explore the best of Lenox and the Berkshires activities and fare! Sitting in this cottage surrounded by forest, you really feel like you are in the shire!

May 19 – 26

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Spring sale! Cabin with views in the Berkshires

The Beaver Dam is a sunlight-filled & recently renovated cabin tucked in the woods, overlooking the October Mountain State Park and steps away from Basin Pond. We are located close to a number of excellent ski slopes. Our cottage is the last house on a private road and right next to protected forest. You can't ask for more privacy, peace and quiet than you'll find at our little piece of paradise on the pond!

Dec 13 – 20

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Sunny carriage house apartment

Our sunny apartment is located midway between Northampton and the Berkshires, in a lovely rural setting. The kitchen, bath and studio living area are in a private apartment, surrounded by 12 acres of open fields. The kitchen is well equipped and includes all the makings for tea and coffee. Orange juice, oatmeal, English muffins and homemade granola are also provided!

Jun 16 – 23

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The old sawmill from 1771

The oldest house in town, fully renovated. Beautiful two-story living room with leafy, private back deck for meals outside. Kitchen with stone counters, gas cook top, and dishwasher; two bathrooms with warm floors. Floorboards upstairs a foot wide; queen size bed with view over the trees, creek and porch.

Sep 19 – 26

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Charming 2BD apartment.

Newly renovated upstairs apartment. Central to all the major attractions. Enjoy a new kitchen with granite countertops. Small town mom and pop market across the street open 7 days. October mountain around the corner. Off street parking. Owner downstairs for any of your needs.

May 10 – 17

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Amazing Berkshire Mountains Cabin

Jun 5 – 12

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Waldtreff - quiet grand cabin

Dec 25 – Jan 1

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Container Cabin in the Catskills (Field)

Dec 18 – 25

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The Creation Station

Jun 10 – 15

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Norbrook Farm ~ Rustic farmhouse w/ pond & trails

Mar 22 – 29

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The Farmhouse - Hot tub eclectic farmhouse 3 br

Sep 8 – 15

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Escape in the Catskills w/hottub

May 16 – 23

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Cozy Condo @ Jiminy Peak

May 28 – Jun 4

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Sunny Berkshire Studio Apartment

Mar 10 – 17

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Dog Friendly Farm Spring bird watching

Aug 29 – Sep 5

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Unique People & Pet-Welcoming Haven

Jan 9 – 16

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Columbia County Getaway - Raspberry Ridge Cottage

Oct 30 – Nov 6

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Secluded but not isolated Berkshire Retreat

Sep 17 – 24

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‘Clavashack’ Country Cottage

May 1 – 8

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Magic Forest Farm's Mountain View Suite

Jul 4 – 11

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Wildlife Lakeside Cottage

Feb 22 – Mar 1

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Modern Barn on 12 acres w Sauna, FirePit+swimming

Nov 12 – 19

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Modern Upstate Cabin, near Rhinebeck NY

May 3 – 10

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Perfect Base for Your Berkshire Adventure

Sep 8 – 15

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Hollywood Bungalow in the Berkshires

Jan 3 – 10

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Lovely cabin by the stream

Aug 3 – 10

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Sunny Inspirit Apartment in best downtown location

Jul 17 – 24

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Need a Getaway??

Oct 21 – 28

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Palazzo Hudson: Luxury Pool, Hot Tub, and Sauna

Oct 6 – 13

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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

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