Hotels in Berkshire County

Prime Berkshires Gem|Sleeps 4|WiFi|Near Tanglewood

Perfect for a family or friend getaway, this property features two luxury pillow-top queen beds, premium linens, a dining table and chairs for work or eating, a sparkling clean bathroom with a shower and a separate sink/vanity area, Roku Smart TV, and individually controlled AC and heat. Quiet, comfy, and comes with full access to East Rock Inn's outdoor dining tables and Adirondack chairs for lounging or enjoying your morning coffee while listening to birdsong. Only 1 mile to Ski Butternut.

The Berkshire Mountain Inn - Garden Room

Bright, cheerful, and unapologetically charming, the Garden Room is a sunny queen retreat in our 1776 historic inn—perfect for skiers and winter getaways. Pink accents throughout the room add a wink of personality (because winter stays don’t have to be beige). Warm up by the inn’s fireplace-lit sitting rooms after skiing Ski Butternut or Catamount, both just minutes away, with downtown Great Barrington only ½ mile away. PLEASE NOTE : NO ELEVATOR. THIS ROOM IS LOCATED ON THE SECOND FLOOR.

The Trail in Adams - Entire Inn (9 guest rooms)

Welcome to "The Trail in Adams" - Berkshires’ Art Hotel on the Ashuwillticook Rail Trail in Adams. "The Trail in Adams" is a 9-room boutique inn located in the heart of Adams. Nestled among world-renowned arts institutions, our artist-decorated boutique inn offers an intimate lodging experience that connects the art, culture, and nature of the Berkshires. Each guest room has its own ensuite bathroom and electronic door lock. Find out more about us on social media @theTrailinAdams

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.  **Additional charge 

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.

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!

Villa in the Berkshires Presidential Suite

2 bedroom- 2 bathroom Presidential Villa suite located in the Berkshires Massachusetts. The location is situated and close to many area attractions. There are plenty of fun things for the kids, including an indoor pool and game room. Perfect for families who want to explore nature, museums, and local culture.

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.

Endless Family Fun: Pools, Arcade Room & Mini Golf

Escape to the Berkshires! Experience hiking, boating, and skiing at our doorstep. Nearby, enjoy the Norman Rockwell Museum, Tanglewood, and the Appalachian Trail. Perfect for families and nature lovers.