Hotel Properties

Our Portfolio

Main Street Hospitality owns and operates properties that have a strong sense of place and express a unique and personal approach to hospitality. Our hotels are distinct, authentic destinations. They are connected to their communities and offer comfort, fun, individuality and style in a meaningful way. Our properties are architecturally significant, while remaining in harmony with their surroundings.

The Red Lion Inn

Stockbridge, MA

The Red Lion Inn has been providing food and lodging to travelers for more than two centuries. The iconic property features 125 rooms and suites – ranging from individually appointed, antique-filled accommodations in the Main Inn to a more contemporary look and feel in surrounding guesthouses. The Inn has four restaurants with formal and casual dining, a pub with free nightly entertainment, a gift shop featuring locally made items and a full range of amenities.

The Briarcliff Motel

Great Barrington, MA

This ‘hip & homey’ classic 60s motel has been transformed into a modern, stylish, affordable lodging option for today’s travelers. The Briarcliff is loaded with personality-  the guestrooms are Instagram-worthy and the cozy lounge area has a great vibe. The lounge is warmed by a roaring pellet stove, the tunes are always on, and the rustic continental breakfast draws everyone together each morning.  Mingle with guests or pick up tips on things to do.  In the evenings, the front lawn fire pit brings friends, families and strangers together.  Plus, we’re in a beautiful location at Monument Mountain, in the heart of the Berkshires, and just five minutes’ drive from Great Barrington, voted Best Small Town in America by Smithsonian Magazine! Come see what all the fuss is about…

The Porches Inn at MASS MoCa

North Adams, MA

The Porches Inn is located directly across the street from MASS MoCA – one of the world’s most renowned museums of contemporary art.  A collection of seven renovated, and now connected, Victorian row houses, the Inn’s esoteric décor reflects an artful, whimsical approach to life. Its retro-industrial architecture mingles with modern comforts and a cutting edge technology to create a design sensibility that can most closely be described as granny chic. A unique blend of color and texture creates a visually engaging experience that showcases a homey, quirky spirit that makes Porches a true original in the Berkshires.

Hotel On North

Pittsfield, MA

Some walls are not precisely straight. Ceiling heights vary. No two guestrooms are exactly alike. Every piece of décor was handpicked for its individuality. You can sip cocktails in a birdcage elevator. Lightning-fast Wi-Fi beams through exposed brick from the 1880s. That’s what Hotel on North is all about. This 45-room former men’s haberdashery is a place where urban styling and 19th Century charm mesh into one uniquely original experience.

Maple Glen at The Red Lion Inn

Stockbridge, MA

Located just footsteps from The Red Lion Inn. Maple Glen is a luxurious lodging option for those looking for traditional ambiance in a vibrant, contemporary setting. Exuberant colors. Eclectic décor. Rustic architecture. New England Charm. The Glen is the ultimate reflection of the Berkshire lifestyle. This 17-room guesthouse comes with a kitchenette, living room and public space that can be used for meetings, wedding parties or family gatherings.

Race Brook Lodge

Sheffield, MA

Nestled at the foot of Mount Race, Race Brook Lodge is the perfect spot for those looking for a tranquil, romantic Berkshires getaway. Surrounded by miles of breathtaking hiking trails and magnificent mountain vistas, The Lodge provides a unique setting for yoga and wellness retreats, weddings, corporate events or just a place to escape the everyday world. The Stagecoach Tavern at Race Brook Lodge is a candlelit gathering spot that has served guests and weary travelers since the 18th Century.