porches inn

The Coolest Historic Hotels In the Berkshires to Visit

The Berkshires are not only full of jaw-dropping natural landscapes and exhilarating activities. They’re also the location of significant historical events, iconic landmarks, and meaningful legacies that continue on to this day. You can even stay at some of these renowned places because they’re also hotels! Next time you visit, check out these historic hotels in the Berkshires for a unique getaway experience.

Red Lion Inn

Silas Pepoon established a small tavern on a Stockbridge street corner in 1773 under the iconic Red Lion sign still swinging today. It was a welcome stop for stagecoaches, a gathering palace for American revolutionaries, and a center of a growing community. Even when a fire burned the entire building in 1896, the town rallied to rebuild the inn and restore its legacy. Since then, the Inn has taken on some modern amenities (including a heated pool), but has kept its small-town charm and eclectic. 

The Red Lion Inn is one of the few American Inns that has been operating continuously since before 1800. Each room at the Red Lion Inn is charmingly unique with different furniture and layouts. On every floor are collections of different art pieces, paintings, and even portraits of some of the famous historical figures who have visited—including five presidents! It’s a luxurious inn with a fascinating history and top-notch hospitality that will make for one of the most memorable stays of your life.

Stay At The Porches Inn 

The town of North Adams, like all the other Berkshire towns, also has a significant place in America’s history. The Porches Inn consists of several houses that once stood as sturdy, detailed Victorian row homes. Instead of tearing them down, businessman Jack Wadsworth renovated the houses. Now they are quirky, upscale homes with long verandas, unique common areas, and mixed striking colors that pay homage to their 19th-century heritage.

Every one of the homes of Porches Inn has a different feel, but the warm, welcoming atmosphere of the hotel remains the same. Just across the street from the historic Mass MoCA museum, your stay here will be unlike any hotel you’ve visited before. Book a stay with us to experience it for yourself!

Deerfield Inn

Originally opened in July of 1884, the Deerfield Inn has been providing exceptional stays and services to customers for a long legacy. It has the atmosphere and charm of the early days, with modern comfort and convenience. It’s no surprise that this corner of the Berkshires has the name “The Happy Valley.” One visit to this place will immediately bring a smile to your face.

The National Historic Landmark still sits on the original site, with the original hayloft doors, front porch, gardens, and horse-shaped wind vane. The surrounding villages, period houses, working farms, and rolling countryside look just as beautiful as they did then. The Inn has added new rooms, modern amenities, and fresh coats of robin’s-egg blue paint to its ceilings, along with electricity, running water, and the warmest hospitality you can find.   

The Hotel on North

Before it was a hotel, this Pittsfield stop was legendary menswear and sporting goods emporium called Besse-Clarke. It’s even on the National Register of Historic Places. Today, the Hotel on North balances its heritage while looking to the future. The owners preserved many architectural features that nod to its past eras, such as exposed brick walls, tin ceilings, decorative columns, and other charming quirks. But, it also sports state-of-the-art technology, modern conveniences, and luxurious amenities to make your stay comfortable and memorable.


The downtown district of Pittsfield is also a mix of history and contemporary draws. Originally a bustling transport center, Pittsfield is the new urban hub of the Berkshires, home to many artists, artisans, purveyors, and entrepreneurs. There’s always something exciting happening just a walk away from the Hotel on North. 

Seven Hills Inn

This Inn started humbly as a small farmhouse in the mid-1700s for early Massachusetts colonists. In 1885, Robin Chapin enlarged the home into a new estate called Norwood, one of the first grand Berkshire Cottages. The estate also became neighbors of Edith Wharton! In 1911, new owners took over and gave the palace extensive renovations, including staircases from England, fireplaces from France, and columns from Italy. In 1951, New Yorkers bought the home and turned it into what is now Seven Hills Inn.


The Inn today sports stylish guest rooms in three different buildings with distinct features: Manor House, Carriage House, and Terrace House. You can see the Inn’s 27 acres of gardens and lawns from Manor House, whereas Carriage House rooms have kitchenettes, and Terrace House has natural lighting from windows facing the tree-lined grounds. Every room has the most modern comforts, Bluetooth radios, large-screen TVs, and complimentary WiFi.

Contact Porches Inn Today 

If you are interested in staying at Porches Inn located in North Adams, MA, contact us today at 413-664-0400. We look forward to your visit!