Stay in hotels and inns where history happened

When you drive up to the picturesque Deerfield Inn, imagine how those early visitors arrived in the 19th century: by stagecoach, carriages and horseback. That sense of history envelops you in this elegant inn, from the 24 rooms (11 in the main inn and 13 in the carriage house) appointed with antiques and period reproduction furniture to the robin’s egg blue ceilings of the charming front porch. The horse weathercock still turns, the original hayloft door is still part of the inn, the garden is still populated with native plantings. And Deerfield, a National Historic Landmark, with its 1774 liberty pole and gorgeous 18th- and 19th-century houses, still feels like the heart of colonial America. Please visit our website to see current COVID policies.

Don’t be surprised if you hear whispers of the past in the corridors of the Hotel on North, the boutique hotel in the center of the Berkshires region. The hotel’s buildings, on the National Register of Historic Places, have a long heritage as the legendary menswear and sporting goods emporium, Besse-Clarke. Many century-old details have been preserved, including exposed brick walls, tin ceilings, decorative columns – even a (stationary) birdcage elevator. But the present is evident here, too, with 45 individually appointed rooms, all with lightning-fast wifi, pillowtop mattresses and luxurious linens. The hotel is minutes away from all the great Berkshires attractions, from art and history museums to cultural venues, ski slopes, hiking, biking and shopping.

The former Westinghouse estate, nestled among the majestic Berkshire Mountains, is now the elegant Ponds at Foxhollow, with 48 condo units, providing guests with all the modern amenities and old-fashioned attention to service and detail that make for the ideal getaway. Each condo unit has a hot tub, full kitchen, dining area, living area and deck overlooking a lovely winding pond. (Canoes on site allow you to enjoy the pond up close.) There are indoor and outdoor pools, exercise room, a gorgeous fireplaced library, tennis courts, putting green and a Friday wine and cheese gathering. History buffs will love being close to museums, historic homes like Edith Wharton’s The Mount, and quintessential New England towns like Lenox and Stockbridge.

What do you get when you combine a celebration of 19th century heritage with modern conveniences like whirlpool tubs and Apple TVs? You get the Porches Inn, where sturdily built Victorian row houses that were once homes to mill workers have been transformed into a wonderful, whimsical inn where every room and suite is unique, from its architecture to its decor. There’s an intentional blend in this inn of old and new: cutting-edge technology and retro furniture and collectibles. You can relax on your private porch, grab a to-go continental breakfast, swim in the heated outdoor pool, then explore the history-rich Berkshires area starting with walkable North Adams, an old mill town now infused with a vibrant arts scene.

Visit our sister properties - Red Lion Inn - Briarcliff

The Harbor Light Inn, among the Ten Most Romantic Inns in America, is set in one of America’s Ten Most Beautiful Small Towns. Near the harbor district and the birthplace of the Navy, the Inn consists of two Federalist mansions joined together. Luxurious rooms are equipped with private baths, DVD players, WIFI, fireplaces, hot tubs and additional amenities for your comfort and pleasure. An extensive continental breakfast buffet is included along with afternoon tea, coffee and cordials. The inn’s popular Tavern serves fine wines, beers and cordials and local favorites like chowder, crab cakes, shrimp, and grilled panini. Within short walking distance, you’ll find shops, galleries, art organizations, museums and historic buildings and sites and a wide variety of casual and fine dining establishments.

Travelers on stagecoaches between Albany and Boston found welcome respite and genial hospitality at the Red Lion Inn when it opened as a tavern in 1773. That year, citizens gathered to protest Britain’s Acts of Intolerance and to propose a boycott of British goods. It was an exciting beginning to the inn’s proud history, which includes visits by Presidents Cleveland, McKinley, Coolidge and both Roosevelts as well as Nathaniel Hawthorne, Thornton Wilder and Bob Dylan. The stately white inn with its renowned front porch (perfect for rocking and beverage-sipping) honors its heritage throughout the property, from its individually decorated antique-filled rooms to the historical posters in the Widow Bingham Tavern to the colonial pewter used in the elegant Main Dining Room.

Visit our sister properties - Briarcliff - Porches Inn