Splurge-Worthy Getaways

When only the best will do.

Looking for upscale lodging, fabulous restaurants, and fun things to do? Our short list of Berkshire must-sees will help you plan your trip! Whether you want to traverse the whole county or stay in a more consolidated area, this list can help you make some great decisions. 

A Visit to the Northern Berkshires

Explore world-class art and nature in Williamstown, Adams, and North Adams.

The Barn Kitchen & Bar at the Williams Inn, credit Great Sky Media

Stay:

The Guest House at Field Farm, Williamstown
Mid-century art and architecture are the centerpiece of this B&B, set on a peaceful 300 acres with views of Mt. Greylock. Savor a farm-fresh breakfast before heading to nearby hiking and nature trails, or drive into town and explore Clark Art and the Williams College Museum of Art. 

The Williams Inn, Williamstown
In the heart of downtown, The Williams Inn offers a contemporary farmhouse vibe perfect for a cozy winter weekend escape. It’s also a good home base for day trips; MASS MoCA, Greylock Glen, and Berkshire Art Museum are within 30 minutes by car. 

Eat:

Freight Yard Pub, North Adams
Equal parts restaurant and casual gathering spot, this well-loved tavern is known for its house-made fare (think juicy sirloin burgers, crispy chicken wings, fresh salads, and hearty entrees) plus a good selection of cold beers on tap.

Casita Berkshires, North Adams
Pull up a seat at this Berkshire farm-to-table Mexican eatery on the MASS MoCA campus for a creative spin on traditional dishes (street corn gnocchi, braised beef tacos) and a whistle-whetting cerveza, margarita, or mezcal.

A Visit to the Central Berkshires

Discover the cultural scene, wellness resorts, and historic inns of the central Berkshires.

Canyon Ranch. Photo by Nicole Loeb.

Stay:

33 Main, Lenox
Conceived and curated by home furnishings entrepreneur and Lenox resident Annie Selke, 33 Main offers a one-of-a-kind stay for the discerning traveler. Immerse yourself in a thoughtfully designed experience where nearly everything you see is a product designed and manufactured by Annie Selke Co.

Doctor Sax House, Lenox
This sophisticated, boutique-style hotel in downtown Lenox has a highly rated on-site restaurant, dulu, and intimate, fireplaced bar for late-night drinks and snacks.    

Canyon Ranch, Lenox
This all inclusive award-winning wellness resort offers Gilded-Age elegance with modern amenities and exceptional service. The food is delicious, and the pampering is spectacular.

Eats

Hand Crafted, Pittsfield
Enjoy thoughtfully crafted food made with locally sourced, ingredient-driven fare. From beloved classics to creative new spins, every dish is thoughtfully prepared with a focus on quality and flavor.

Haven Café & Bakery, Lenox
Haven is popular for brunch (go early) and meet-ups over fresh-brewed coffee (the maple cardamom latte is worth the splurge). Don’t miss their signature carrot cake and other fresh-baked delights in the bakery case at the counter!

Alta Restaurant & Wine Bar, Lenox
Mediterranean-inspired cuisine, an extensive wine list, and excellent service have earned Alta a loyal following in the busy Lenox restaurant scene. Grab dinner, or sit and sip at the bar.

The Old Inn on the Green

A Visit to the Southern Berkshires

The southern Berkshires is home to historic inns and picturesque downtowns.

Stay:

The Old Inn on the Green, New Marlborough
The rural location nearly guarantees privacy, and the well-appointed guest rooms offer modern comforts with Old World romantic charm. Dine by candlelight on innovative dishes created by Chef/Owner Peter Platt.

1800 Devonfield Inn, Lee
Step into luxury at this top-rated B&B, centrally located between Lenox and Stockbridge. Start your day with a fresh country breakfast before hitting the sites.

Eats

Dream Away Lodge, Becket
Set in a 200-year-old farmhouse near October Mountain State Forest, this restaurant, bar, and music venue brings together locally sourced, delicious food, live music, and atmosphere found only here in the Berkshires.

You deserve a splurge! Find more places to play, stay, and eat with our Official Guide to the Berkshires. Want to learn more and explore even more of the Berkshires? Visit berkshires.org, as this is the quintessential Berkshire planning tool for all your local needs.

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