Stay in hotels and inns where history happened

Two elegant Federalist mansions make up the lovely Harbor Light Inn, where its 18th century past is celebrated in everything from hand carvings to finely tooled furnishings to paintings and other artwork. Stay in a room with a four-poster or canopy bed, with a working fireplace and cozy window seating, and you’ll feel you have slipped back into a more serene time. The gracious inn is located in Marblehead’s historic harbor district, not only close to shops, galleries and restaurants but also to other colonial homes. Guests can get a glimpse of this famous sailing town’s past at the Marblehead Museum or by visiting Old Burial Hill, with gravestones going back to the 1600s. The inn’s modern amenities include an outdoor pool and popular tavern.

You can stay at a hotel where all the rooms are alike, or you can stay at the one-of-a-kind Hotel on North, where each room has its own character and each piece of decor is handpicked for its individuality. The 45-room hotel’s history, as a famous menswear and sporting goods emporium, means you’ll find exposed original brick, tin ceilings, decorative columns – even a birdcage elevator where cocktails for two are served! Some rooms in the hotel, on the National Register of Historic Places, have wet bars and gas fireplaces; all have original art and locally crafted furniture. Casual dining is offered in the Berkshire Palate restaurant. It’s a short drive to art museums, Hancock Shaker Village, and dance and theater venues.

When the Deerfield Inn opened its doors to guests in 1884, they came by stagecoach, carriage and horseback to enjoy the inn’s warm hospitality. Today, that tradition continues, with uniquely appointed rooms, most with period reproduction furniture and antiques, hearty meals served by a crackling fire in Champney’s restaurant and tavern, and a comfortable front porch with a ceiling still painted robin’s egg blue. The original hayloft door is still at the inn, the horse weathercock still turns and floors in the main inn still offer unexpected turns. Stroll down Main Street past gorgeous 18th- and 19th-century houses or get up close and personal to the historic town’s roots at the Flynt Center of Early American Life or Memorial Hall Museum.

The Ponds at Foxhollow has been part of the Berkshires scene since the late 19th century, when George Westinghouse built a “cottage” on the 223-acre estate for his wife, Marguerite. The estate, originally called Erskine Park, went on to do service as a girls school for 40 years in the mid-20th century. Today, it welcomes guests seeking a respite in a scenic, secluded resort with in-room amenities including fireplaces, decks overlooking the pond, fully equipped kitchens and jetted tubs. Two-bedroom condos have loft sitting rooms. The resort has indoor and outdoor pools, a fitness center, hot tub, sauna, a playground and courts for tennis, bocce and basketball and is close to the region’s great restaurants, museums, recreational activities and arts venues.