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Cozy Queen at The Whitlock Lenox

Tucked inside The Whitlock, a historic 1820 boutique inn on Church Street in the heart of downtown Lenox, the Cozy Queen is a warm, thoughtfully appointed room with one queen bed, ideal for couples or solo travelers. Step out to the shops and galleries of the village, or make the 2 minute trip to the Tanglewood gates. Back home, gather by the outdoor fire pit, settle into a firelit parlor, and enjoy specialty coffee drinks available 24/7. Your key code arrives before you do, so simply settle in.

Historic Beaver Mill Inn, Room 1

Located beside Natural Bridge State Park and just three minutes from MASS MoCA, downtown North Adams, and MCLA, the 12-room Historic Beaver Mill Inn combines the character of a restored industrial landmark with the comfort of contemporary private guest rooms, a communal kitchen, and ample common space. Sorry, no guests under 18, no smoking, no pets, 2-night minimum; discounts for 3-night, 6-night, and 12-night+ stays. Free admission to the Berkshire Art Museum; guided art studio tours.

Standard Queen at Hideaway Inn Lenox

The Hideaway Hive is a bright, cozy retreat for couples and solo travelers at Hideaway Inn Lenox, a design forward boutique hotel in downtown Lenox, MA. One comfortable queen bed, A/C and heat, mini fridge, TV, and private bath cover the essentials, while direct to door arrival and 24/7 specialty coffee keep it effortless. Walk to restaurants and shops, catch a show at Tanglewood just 3 minutes away, and unwind on the porch or at the fire pit. Your perfect Berkshires basecamp.

Hudson Whaler Hotel - Queen Deluxe 203

Beautifully designed with a queen bed, desk, modern bathroom with a multi-spray spa shower and bathtub. All of our suites have an electric fireplace, Smart TV, Cable, Complimentary WiFi, Refrigerator, Keurig Coffeemaker, In-room Safe, Heat/AC and an Iron/board. Enjoy Soap/Shampoo/Conditioner, Lux Bedding, Towels, En-suite Bathrooms, firm euro-pillow top mattress, and in-room amenities for purchase. This is a second floor room. We do have an elevator!

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.

Steps from Stockbridge Main Street | Dining & 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.

2 Full XL beds

This inviting 1-bedroom retreat in Becket is your perfect escape to the peaceful Berkshires. Featuring two extra long Full-sized beds, air conditioning, heating, Wi-Fi, in-room coffee and a mini-refrigerator, it’s designed for comfort and convenience. Surrounded by nature, it’s a great spot to relax lakeside or explore nearby trails and attractions. Whether you’re unwinding or adventuring, this cozy haven awaits!

The Reclaimed Motel, Hudson Valley - Three Farmers

Moving the past forward The Reclaimed Motel was built in 1960, and we wanted to respect its mid-century bones while making thoughtful modern upgrades. And the list of upgrades was long! From a new roof, to all new plumbing and electric, we've kept the integrity of this Red Hook landmark while investing in meaningful improvements to make this motel appealing and memorable for the modern traveler.

Hudson 4 at The Argus Hotel

Hudson 4 is a first floor queen room with private bathroom. Each room is equipped with a SmartTV and Apple TV as well as a desk. This room is pet friendly. Complimentary Services: Continental Breakfast Onsite Parking Electric Parking Wi-Fi & Apple TV Keyless Entry Ensuite Guest Rooms ​ Paid Services: Cocktails Meeting Space Rentals Pets (If applicable) Early Checkin (1PM) Late Checkout (12PM)

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!

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.