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Berkshires Family Oasis with Hot Tub, Patio, Gym

All seasons family retreat in PRIME Berkshires location. Located adjacent to the famous Appalachian trail, 5 minutes from downtown Great Barrington, 2 minutes from Ski Butternut and 15 minutes from Tanglewood in Lenox. Easy access to sensational hiking, dining, lakes and museums. The home is spacious and open with 4 BR, 7 beds, a large finished basement TV & game room space and backyard patio and hot tub. A perfect spot to enjoy the spectacular beauty and unlimited activities of the Berkshires.

Sunbeam Lodge: Pool+Sauna, 50 Acres, ‘70s Oasis

Our peaceful, skylit, 3-bed 2-bath lodge is a totally private woodland paradise on a quiet country lane. Part secluded retreat, part rustic resort, part '70s-style cottage, it's only 2 hours from NYC & 20 minutes from Hudson. Unwind in 50 acres of untouched forest & grounds, a seasonal saltwater pool & cabana bar, a Finnish sauna & 7-person hot tub (open year-round), an open chef's kitchen & living room, & a sunny deck overlooking endless natural splendor. See more @sunbeamlodge on Instagram.

Modern & Cozy Cntr Square Townhouse Gem from 1854

This amazing Airbnb will give you all the comforts of home! Tastefully decorated with everything you need and then some!! -> Grab-N-Go items (Coffee, Tea, Light Snacks) -> Smart LED Tvs in (2) Livingrooms & (2) Bedrooms -> NordicTrack & Peloton bicycles -> Smart locks with keyless entry -> Fast wireless WiFi -> Queen beds with premium mattresses & pillow covers -> Fully equipped + utensil stocked kitchen + Keurig Coffee -> Full size washer/dryer And much more so come and enjoy your stay!

"Hemlock Shadow" near Tanglewood on Six Acres

Hemlock Shadow is located on 6 acres of native and wild forest and features a small stream and pond located at the bottom of the property. It is centrally located near Lenox, MA and is only 1 mile up the hill from Tanglewood and all of the amenities the surrounding area offers. You will find excellent hiking trails within walking distance of the house. This minimalistic home offers an in-forest oasis where you can escape your troubles and enjoy the majestic nature afforded by the Berkshires.

Antique Uptown Charmer w/ Five-Star Modern Kitchen

The best of modern designed paired with authentic historic Kingston bones. The house features 3 full luxe baths, HUGE new chef's kitchen with endless work surfaces - 3 ovens, and baking equipment galore. 2 full floors (+basement) offer room to cook and play, flowing from the kitchen to the dining deck to the hot tub deck. This freshly restored home will be your base camp for adventures, but once you come you won’t want to leave!Quiet workspaces, printer, choose your vibe to get work done.

Cozy chalet w/ fireplace near Hudson & hiking

Cozy 3-bedroom (5-beds), 2-bathroom home on 4 private acres in charming Ghent, NY. Recently renovated, Arch Bridge Chalet offers modern clean comfort with an open floor plan, luxury bathrooms, high-end appliances and cookware, a wood-burning fireplace, outdoor deck, and fire pits. Surrounded by trees, trails, and streams, yet close to Hudson Valley farms, breweries, Berkshires skiing, and the vibrant town of Hudson. Perfect for hiking, biking, kayaking, skiing, and year-round getaways.

Hidden Oasis in the Mountains by Evergreen Home

Evergreen Home Vacation Rentals invites you to this hidden oasis in the heart of the Berkshires. This attractive 5-bedroom home features a large, fully-outfitted kitchen, Tuft & Needle mattresses, and stunning mountain views. Relax in the hot tub, enjoy the perennial gardens, or gather on the stone patio by the fire pit. Just 7 minutes to Bousquet Mountain and minutes from Lenox and Tanglewood, this is the perfect retreat for family and friends. Experience luxury and comfort—book today!

Boho-Chic Cape Conveniently Located

Enjoy a spacious yet cozy home in a quiet neighborhood with off-street parking. Minutes from restaurants, shopping, universities (UAlbany, Sage, St. Rose), parks, museums, hospitals(Albany Med, St.Peters) and State Capital Offices for those traveling for business. We’re right off the main highway leading to the World Famous Saratoga Race Track (30 min) and Adirondack Mountains/Lake George (50 min)! From this Air Force Family to yours, welcome to our home.

Bright, Airy Home in Hudson w/ TONS of Character!

Welcome to 514 Route 66! Conveniently located 5 min from historic Warren St, this bright and stylish country home is just minutes from downtown Hudson, where you can enjoy fine-dining restaurants, hip cocktail bars, art galleries, antique shopping, and more. Or, just relax, stay home, and sip coffee or wine in the sun-drenched living area, beneath the vaulted ceiling. A perfect mix of town and country, for a perfect upstate weekend.

Spacious Lenox Farmhouse | Retreat Near Tanglewood

Welcome to Green Garden! This charming 3 bedroom, 2.5 bathroom New England farmhouse is your new favorite retreat in the Berkshires. After a day of exploring, kick back by the glow of the fire pit or relax inside. Minutes from Tanglewood and downtown Lenox, you’ll enjoy farmer’s markets, great dining, and peaceful star-filled nights. The house is kid-friendly with a Pack ’n Play, Tripp Trapp high chair, and Inglesina Fast Table.

Into the Woods- Berkshire Cabin Retreat!

Into the Woods- Berkshire Cabin Retreat Ditch city living and get lost in our majestic forest. Surrounded by lofty trees, this heavenly cozy cabin is your chance to curl up by an iconic wood-burning stove, sip coffee on a wrap-around porch while listening to the music of wildlife, roast s'more by the fire pit, or pour yourself a glass of wine and choose one of the many adorable rooms to retreat to.

Rabbit Run in the heart of Stockbridge Village

Old meets new in this lovely cottage, a short walk from the Red Lion Inn. Lots of light, comfortable, traditional furniture, beautiful, fenced-in backyard with mountain views. Kitchen updated with Smeg refrigerator, gas stove, granite counters, hardwood floors throughout. Hiking trails, park, and tennis courts within a 5-minute walk. Lake rights to Stockbridge Bowl, Weber grill, and Solo firepit.