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Historic Barn Stay at Gedney Farm

Welcome to Gedney Farm, 50 acres of rolling pastures and high open meadows in the historic village of New Marlborough. Originally built around 1906, our Lodging Barn has been imaginatively transformed into a premier boutique hotel experience. Every room features its own distinct layout, individually furnished decor, and a private bathroom. Many of our spaces feature spectacular vaulted cathedral ceilings, granite-surround wood-burning fireplaces, and deep whirlpool tubs perfect for unwinding.

Peaceful Berkshires Escape – 2BR Resort Condo

After a day of mountain adventures , our Resort in the Berkshires is the perfect New England-y place to unwind and kick off those hiking boots. Take the whole family for a relaxing indoor swim, enjoy a flick at our onsite movie theater, and end your evening with a toast at the Beartree Bar. • Pools, Gym, Movie Theater and mini golf  • Accommodate up to 6 people  • One guest in the party, must be at least 21 y/o or older.    * U$10 PER NIGHT OF RESORT FEE(WAIVED) .  **Additional charge 

The Becket Motel - Queen Bed *

Situated in the charming mountain of Berkshire, MA. The Becket Motel is close to a variety of area attractions, including hiking, cultural activities, and shopping. Jacob's Pillow Dance, Tanglewood, Museums, Becket Arts Center, and more. The Becket Motel is a place to take a vacation in an inspiring place and enjoy the outdoor attractions. The motel features comfortable accommodations, with a private bathroom with a bathtub In each room microwave, a mini-fridge, and a coffee machine.

Springs Motel Honeymoon Suite

Experience retro charm and modern comfort in our Honeymoon Suite at The Springs Motel. This beautifully designed suite features a spacious king bedroom, a cozy living area with a pull-out couch, and a dining space, all adorned with unique vintage decor. Enjoy the convenience of two full retro-tiled bathrooms, a private patio, and access to our seasonal front lawn lounge. You’ll love the stylish decor of this charming place to stay.

New England Landmark + 4 Dining Spots Onsite. Pool

Step into a living legend at The Red Lion Inn—welcoming travelers since 1773. In the heart of walkable Stockbridge, you're just 2 miles from the Norman Rockwell Museum, minutes to local shops, and surrounded by art, live music, and unforgettable food. Sip tea on the iconic front porch, dip into the year-round heated pool, catch a speakeasy show downstairs, or bike through town. It's all here—classic New England with a twist.

The Central Downtown Inn

The Central Downtown Inn & Suites – Comfort & Convenience in the Heart of the Berkshires Welcome to The Central Downtown Inn & Suites, a modern and upscale guesthouse in the heart of Pittsfield. Whether you're here for a weekend getaway, a business trip, or a family vacation, our thoughtfully designed accommodations ensure a comfortable and hassle-free stay. Prime Location, Unmatched Convenience.

The Berkshire Mountain Inn - Federal Room

The Federal Suite is a cozy queen room inside The Berkshire Mountain Inn, our historic 1766 inn refreshed for modern comfort. Plush bedding, blue-and-white touches, and a sunny seating nook set a relaxed mood. Enjoy a desk, streaming TV, and your own in-room fireplace for extra glow and romance—perfect for a Berkshire escape. PLEASE NOTE: NO ELEVATOR. SECOND FLOOR ROOM.

Little Cat Lodge -King room

Merging the rustic charm of an alpine lodge with the magic of mid-century Berkshires, our 400 sq. ft. King rooms are lined in mushroom wood, outfitted with a custom twin daybed, and accented by original artwork. Built in storage and a private terrace or patio ensure you can make the most of your mountain stay. Mini fridge and Keurig included!

Little Cat Lodge - Double Double

Merging the rustic charm of an alpine lodge with the magic of mid-century Berkshires, our 400 sq.ft. Double rooms are lined in mushroom wood and accented by original artwork. Built in storage and a private terrace or patio ensure you can make the most of your mountain stay. Mini fridge and Keurig included!

Mezze Guesthouse - Two Bedroom, sleeps 4

Experience luxury contemporary lodging alongside culinary excellence at the new Mezze Guesthouse. Accessed via a separate entry directly adjacent to Mezze Bistro + Bar, ascend the stairs to this Two Bedroom Unit, which exudes stylish and calming vibes of custom, one-of-a-kind finishes by local artisans.

Berkshires Retreat | 1 Unit |Pool & Fitness Center

Set in the scenic Berkshires, this resort offers easy access to outdoor activities and cultural attractions like Tanglewood and Norman Rockwell Museum. Guests can enjoy spacious accommodations surrounded by nature, making it an ideal spot for a countryside retreat.

Wyndham Bentley Brook 2 BR

Ski-In/Ski-Out Plus Year-Round Mountainside Fun. The Wyndham Bentley Brook is situated right at the base of Jiminy Peak ski mountain, making this resort an exceptional choice for mountainside play. In winter, ski out your door and onto the lifts.