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Rustic Secluded Cabin near Berkshires. *wood stove

The Red House offers a peaceful secluded retreat, surrounded by acres of forest & with excellent hiking trails. Enjoy the tranquility of nature while being minutes from antiquing, Kripalu, the Norman Rockwell Museum, The Mount, Tanglewood, skiing, & Shakespeare & Co. You'll appreciate the serene privacy, situated on an old dirt road. Relax by the wood stove or in the sunroom. Nearby towns of Spencertown, Chatham, & West Stockbridge offer unique charm. 4WD vehicle is recommended for winter visits

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna

Nestled in the serene woods of Saugerties, NY, this luxurious A-frame cabin offers modern comfort and natural beauty. Just 10 mins from Woodstock and 2 hrs from NYC, NJ. it sits on a private 2-acre lot. Easy Access. Featuring premium queen Casper mattresses, a Breville espresso machine, a 4K projector, a firepit, grill, a cedar wood-fired hot tub & Sauna. Dog friendly! A cozy & stylish retreat near hiking, skiing, and top dining spots in the Catskills. Visit our ig ‘highwoodsaframe’ for more!

Haddock + Cotter - Chic Farmhouse and Barn w/ Pool

This beautifully restored 1834 farmhouse blends historic charm with chic, modern comfort. Perfect for hosting family and friends, a holiday getaway, or a quiet country escape - designed for both relaxation and connection with cozy, elevated interiors. *Pool surrounded by lush gardens & a pergola *Barn converted into a luxe pool house *Basement gym (Peloton, punching bag,yoga&more) *Bar cart stocked for cocktail nights *Private, secluded setting immersed in nature Follow on IG @haddockandcotter

Fall Foliage Luxury Cabin & View Autumn Adventures

Welcome to our mountain retreat, nestled in the heart of nature and brought to you by Den Outdoors. 25 mins to Tanglewood, 35 mins to Jacobs Pillow, 15 mins to Jiminy Peak, 30 mins to The Clark, MASS MoCA, and the Berkshire region. 10 mins to a swimmable lake. 2.5 hrs from NYC and from Boston. Come experience all Autumn has to offer! Stunning views, no visible neighbors, Goodland wood fired hot tub, Breeo Fire pit, large Webber Grill, radiant floor, EV charging, and the MOST STUNNING view!

Barn Stay at Shadowbrook Farm

Welcome to the Shadowbrook Farm Stay. Tucked in the hills of upstate New York, this 1700's Shaker barn has been restored into a beautiful guest house. It sits upon a two hundred acre working pasture raised meat farm. This barn was used to hold, and milk cows for two hundred and fifty years. Guests will have access to portions of the farm lands which are highlighted on the maps provided in the Farm Stay manual. If you follow the farm road, you are able to meet every farm animal on the property!

NEW! Berkshires Farmhouse w/ Firepit & Wood Stove

Welcome to our little slice of heaven upstate. Located just a 5-minute drive to the MA border, a stay at our home in Canaan, NY means access to the best of both Columbia County and the Berkshires. In the summer, enjoy the private Adams Point Beach on Queechy Lake and easy access to Tanglewood. In the winter, explore 4 different local ski resorts and curl up by the cozy wood stove. In between, enjoy the peaceful pond views and secluded location on a dirt road. We can't wait to welcome you!

Berkshire Queechy Lake Haven

Private ,clean, cozy cottage on beautiful Queechy Lake. Easy access to all attractions, wineries breweries, & restaurants . Soapstone counters, farmhouse sink, large furnished screen porch/lanai, comfy beds, yard, wood stove, high Spd WI-FI, fire pit, barbeque. Apple picking 5 min,-walk or bike around the lake - private beach access. Paddle board, canoe from backyard. Lenox 20 min, Chatham 15, Hudson 35, Pittsfield 20. Welcoming cottage and home base to all the area has to offer.

Berkshires/Pet Friendly/Tanglewood/Private Ranch

Pet-Friendly, Child-Friendly Getaway! Modern suite with full kitchen on private horse ranch. Wake to horses in the fields, hiking, breakfast on your patio. Perfect location for individuals, couples, families animal lovers. Near all ski areas (Jiminy Peak/Catamount/Bousquet /Butternut), shopping, museums (Norman Rockwell/Mass MoCA) wine tasting (Balderdash Cellars, Hilltop Orchards) Tanglewood, Jacobs Pillow, Miraval, Kripalu, Canyon Ranch. Trail Rides /Horse activities available by appt!

Berkshire Lakefront House with Amazing Views

Enjoy the culture of the Berkshires & Hudson - 15 min from Tanglewood, Norman Rockwell Museum, Shakespeare & Co, PS21, McHaydn Theatre, Mount Greylock, Jiminy Peak Resort, zipline parks, Bousquet & more. Restaurants & market within driving distance and a membership-only beach within a short walk or drive. Great lake views with wrap-around porch. The lake is family-friendly. We welcome couples, solo adventurers, and families. Sorry, no "Group Bookings" - book & pay via one account only.

Modernized 1860s Getaway w/ Queechy Lake Passes*

Unwind in our quiet, spacious, light-filled, rural home without leaving modern conveniences behind. Located in Historic Lebanon Springs, our newly restored antique home is near both Hudson Valley restaurants and shops and the Berkshire's vast outdoor activities. We took great care to save this home's historic details while creating a fully modernized, comfortable retreat. Every room is thoughtfully curated with local antiques, artwork, and many unique touches you'll enjoy.

Hiking Nearby! Hot Tub, Movie & Game Room!

Welcome to your all-season escape in the heart of the Berkshires & Hudson Valley! Stretch out and relax in this cozy, stylish home that feels worlds away—yet is just minutes from everything. Whether you’re here for skiing, concerts at Tanglewood, wine tasting, or farm-fresh markets, you’re perfectly positioned to enjoy it all. ☀️ SUMMER BONUS: Your stay includes exclusive access to Queechy Lake’s private beach—perfect for sunbathing, swimming, and lakeside lounging.

Cozy cottage on peaceful pond

This little slice of heaven is located on the serene Richmond Pond. Right down the street from Balderdash winery and a 15 minute drive to charming downtown Lenox and Tanglewood. In Lenox you can find great dining, shopping, and there is plenty of hiking and biking around this area. This cozy cottage has everything you need for a Berkshire retreat. In the fall cozy up next to the fireplace inside or out take a break and unwind at this Peaceful oasis.