A curated travel guide · Western Massachusetts
The Berkshires are defined by independent businesses, artists, farmers, musicians, chefs, and innkeepers. When you visit, staying at locally owned inns helps preserve the character and community that make this region special.
Explore Local InnsThe Berkshires, honestly
People don't travel to the Berkshires for chain hotels.
They come for the farm-to-table restaurants, historic villages, live music, art galleries, bookstores, hiking trails, and the independent spirit that defines this region.
From chefs and artisans to musicians and innkeepers, small businesses shape the Berkshires experience. Choosing locally owned accommodations helps sustain the community that makes this destination unique.
Why Stay Local
You're greeted by the people who actually shape the place — not a corporate front desk.
Local inns hire locally, source locally, and reinvest in the villages you came to enjoy.
Restored farmhouses, historic taverns, and small lodges — each with a story you can feel.
Featured Inns
A small, hand-picked collection of locally owned places to stay across the northern, central and southern Berkshires.
Sheffield
★ 9.6Our favorite for its vintage farmhouse character, thoughtful design, and modern comforts.
A beautifully restored Berkshire farmhouse blending historic charm with modern upgrades for comfort and convenience. Wilder House offers cozy design, peaceful surroundings, and is close to everything - hiking, waterfalls, food, music, and more.
Great Barrington
★ 9.4A stylish and intimate Berkshire stay.
Thoughtful details, calm interiors and a relaxed atmosphere — a small-scale boutique stay made for slow mornings and unhurried afternoons. With a pool table and dedicated room for listening to records, this vintage house is a fun place for a quiet weekend.
Great Barrington
★ 9.1Walking distance to Great Barrington
A historic Victorian retreat in Great Barrington, Massachusetts. Experience charming lodging accommodations with modern upgrades and a convenient location in great barrington.
South Egremont
★ 9.2A classic New England inn with timeless Berkshire character.
A classic New England Inn with an onsite restaurant and music venue - The Barn, bringing touring bands into a hip, rustic setting.
New Marlborough
★ 9.5Romantic countryside inn with a celebrated farm setting.
A beloved destination known for its restored barns, soft pastoral views and on site restaurant that's a reason to visit on its own. Gedney Farms is a beloved wedding venue for much of the summer, but you can also book rooms for getaways.
New Marlborough
★ 9.2One of the Berkshires' most iconic historic inns.
Colonial-era rooms lit by candlelight, fine dining that draws guests from across New England, and a sense of place you can't manufacture. Relive the 18th century in this longstanding mainstay of the Southern Berkshires.