Chatham Bars Inn
Cape Cod, Massachusetts

Long before Cape Cod was the idyllic summer destination, so loved by celebrities from Taylor Swift and Carly Simon to Harry Connick Jr. and Spike Lee, it was the favorite hunting grounds for three generations of Boston stockbroker Charles Hardy’s family. He was so confident that others would come to love the soft sea breezes and calming shores of the Massachusetts region that he built an extravagant hunting lodge in Chatham, opening up Chatham Bars Inn in 1914.

The grandeur had not been seen before in its day, complete with private bathrooms with both fresh and saltwater baths and soundproofed rooms. One of the highlights was looking out over the waters of Aunt Lydia’s Cove from the veranda to take in its sunset.

Over the decades, prominent names from Henry Ford, William Rockefeller, and the Dutch Royal Family checked in—and thanks to a major 2006 renovation, the 112-year-old property is still rooted in Hardy’s vision: offering the most lavish details of the day set in a stunning seaside setting.

The Colony Hotel
Kennebunkport, Maine

Hotelier Reuel Norton had fallen in love with—and saw the potential of—Maine’s Cape Arundel as a beach getaway and started building up properties in the region. So when it came time to create his dream project, he turned to architect John Calvin Stevens to develop this Colonial Revivalism masterpiece, making its debut as Breakwater Court shortly before World War I broke out. After Norton’s passing in the 1920s, the hotel stayed in the family for decades until it was sold to fellow hoteliers George and Agnes Boughton.

The couple already owned The Colony Hotel in Florida’s Delray Beach, so they changed its name to match its southern sibling’s, and the hotel was groomed and grown into the 140-room coastal escape it is today, still radiating with New England throwback charm. Its place in history is solidified by being registered as one of the contributing structures to the district’s U.S. National Register of Historic Places, as well as being welcomed into the Historic Hotels of America in 1999.

The Kendall
Cambridge, Massachusetts

Cambridge’s Kendall Square is where the first phone call ever was received in 1876 and where the first email message was ever sent in 1971. It's also where Engine Co. 7 was built in 1895, a marvel of its time as a standalone firehouse, in an age where most shared buildings with police stations or other city offices. Needless to say, this neighborhood had long been at the forefront of innovation—which also meant it understood when it was time for the fire trucks to relocate to a new facility in 1993.

But that wasn’t the end of the life of the 131-year-old fire station, designed by architects R.J. Fitzgerald and S.D. Mitchell of Boston, complete with stables for its horse cavalry, steam pumpers, coal bunkers, and firefighter dorms. Artist Charlotte Forsythe and her developer husband Gerald Fandetti saw the potential in the abandoned building in 1999 and transformed it into the 77-room boutique hotel The Kendall, retaining its historic Queen Anne-style integrity every bit of the way. And the odes to the past continue: the on-site restaurant Black Sheep Restaurant opened this year with its name honoring one of the company’s most legendary fireman.

Hanover Inn Dartmouth
Hanover, New Hampshire

Back in 1769, Dartmouth College was founded on the premise of giving equal educational opportunities to Indigenous students. Though it took two centuries to establish a proper Native American program, the Ivy League university has grown into a 269-acre campus set alongside the Connecticut River that’s the very definition of collegiate—so much so that President Dwight Eisenhower said during his 1953 visit, “This is what a college should look like.”

Running parallel to the school’s legacy has been The Hanover Inn, sitting adjacent to the campus’ grassy square, the Dartmouth Green. Opened in 1780 as a tavern, its storied halls have welcomed numerous Presidents, including James Monroe, Woodrow Wilson, Franklin D. Roosevelt, Dwight Eisenhower, Richard Nixon, and Ronald Reagan, as well as literary greats F. Scott Fitzgerald, Duke Ellington, J.D. Sallinger, and Robert Frost, and performers ranging from Duke Ellington and B.B. King to Mary Tyler Moore and Ella Fitzgerald.

Inn at Perry Cabin
St. Michaels, Maryland

Named after the archangel of the same name, St. Michaels was established as an Episcopal parish in 1672 and grew into a shipbuilding town. But it was during the War of 1812 when it cleverly got ahead of a 1813 British attack that it earned the moniker “The Town That Fooled the British.” A couple years later, Commodore Oliver Hazard Perry’s war aide Samuel Hambleton designed Perry Cabin as a manor.

Over time, the site has had lives as a plantation and riding academy, but it’s shined most as a hotel, eventually becoming the Inn at Perry Cabin. While it received various upgrades over the years, it was the 1999 addition of the Crescent Suites by the Orient Express that solidified its status as the region's most luxurious stay.

Wayfinder Newport
Newport, Rhode Island

While so much of American colonial times were rooted in religion, Newport was founded in 1639 on the concept of religious freedom, drawing a diverse population, including the Jewish and Quakers. Before long, the town was considered one of the nation’s leading seaports. By the time the Revolutionary War came around, there was such a patriotic spirit in town that the British made it their target, occupying it from 1776 to 1779.

That period shifted Newport’s personality, as it rebranded itself as a cultural hub, drawing artists and designers and architects and scientists, giving way to the Gilded Age, the era the city now holds onto best, with landmarks like The Breakers, Marble House, and The Elms. And it’s against this backdrop that the Wayfinder Newport also reinvented itself, turning an old motor lodge into a chic 187-room retro boutique property.

Explore more resorts and hotels across the Benchmark Resorts & Hotels portfolio, a collection of distinct, independent properties by Pyramid Global Hospitality. Located in diverse destinations across the globe, Benchmark’s resorts and hotels reimagine immersive travel, inspiring guests to create memories born from meaningful exploration, authentic moments, and innovative experiences – no matter the occasion. Benchmark guests can earn complimentary gift cards, on-property perks, and destination experiences through the collection’s signature Mosaic Rewards program.