Hotels in Berkshire County

Prime Berkshires Gem|Sleeps 4|WiFi|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 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

Bright 2BR Condo – Perfect for Family or Friends

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.

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.

Walk to Local Museums | Bikes. Porch & Pool Access

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.

Historic Inn 1773 + Pool, Spa, Bikes, Dining

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.

Walkable Stockbridge + Headed Pool & Bike Rentals

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.

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.

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.

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.