The Kelley House Hotel in Edgartown, Massachusetts, opened in 1742 as The Tavern, and served as a respite for sailors during the Revolutionary War. Booking can be a bit pricey — a one-bedroom suite can range from $400 to $600 a night — but if you're looking to explore Edgartown's history, this is the place to stay.

Kelley House Hotel

The Historic Inns of Annapolis is made up of three buildings in Maryland, the oldest of which was built in 1727. Today, visitors can enjoy modern amenities like Starbucks, or have a meal at the Treaty of Paris Restaurant and Drummer's Lot Pub; pricing for a room begins around $130 a night.

Historic Inns of Annapolis

The Beekman Arms has welcomed guests since 1766, and remains a central gathering place in Rhinebeck, a charming upstate New York town with estates nearby that belonged to the Roosevelts and Vanderbilts. Guest rooms start at $200 a night, and are decorated to resemble olden times while still having modern charm.

Beekman Arms

In 1771, Colonel Ebenezer Crafts, now called the Publick House Historic Inn, opened in Sturbridge, Massachusetts, and rumor has it that Crafts acquired the land after winning a card game. Starting at $69 a night, its three buildings are quaint and charming, and no stay is complete without visiting the 18th-century bake shoppe.

Publick House Historic Inn

The Red Lion Inn opened in 1773 in Stockbridge, Massachusetts, but was purchased by Charles H. Plumb and his wife, a collector of antique furniture and china, in 1873. The building burned down in 1896 but was completely rebuilt the next year, and Mrs. Plumb's antiques are still on display at the inn today, where rates start at $170 per night.

The Red Lion Inn