America's Weirdest Theme Hotels

Key Largo, FL

Guests need scuba training—offered on site—to check into this hotel's underwater suites. Incredibly, there's room service: Staff divers will deliver well-wrapped pizzas from local restaurants ($500 per person per night; jul.com).

—Amanda Pressner

Cottonwood, ID

Originally a roadside attraction, this massive wooden beagle is now a B&B. Alongside, there's a port-a-potty hidden in a 12-foot-tall fire hydrant (dogbarkparkinn.com).

Holbrook, AZ

1940s road-trippers witnessed the country's brief profusion of "wigwam hotels." A few remain, like this Arizona property where guests sleep in freestanding concrete tepees (doubles from $54 per night; sleepinawigwam.com).

Parthenon, AR

It took four years to turn this Ozarks cave into a hotel. Dehumidifiers keep dampness at bay, and natural sunlight penetrates the space through large windows (from $450 per night; beckhamcavelodge.com).

Boston, MA

For more than 100 years, this riverside property was a prison with a view. Today, it's a luxe hotel that retains the cell doors and catwalks from its past life. Visit Clink restaurant for crisp-seared Berkshire pork belly from Eleven Madison Park escapee Joseph Margate (doubles from $295; libertyhotel.com).

Litchfield Hills, CT

The Winvian's helicopter cottage houses a 17,000 lb chopper that's been turned into a private lounge. Want something cozier? Choose from the woodland compound's 18 other quirky rooms, like one modeled after the inside of a beaver's den (doubles from $650; winvian.com).

Mt. Tremper, NY

True to form for flamboyantly retro B-52s singer Kate Pierson, her Catskills retreat is awash in vintage kitsch. Multihued appliances complement Midcentury-Modern sofas and easy chairs (cabins from $175; lazymeadow.com).

Fairbanks, AK

Owners Mike and Sue Wilson pieced together their B&B from retired railroad cars, hauling them one by one to this ridge overlooking Fairbanks. The newest is an 85-foot-long dining car (double cars from $145; fairbanksalaskabedandbreakfast).

Portland, OR

Chalkboards hang on the walls of the classrooms-turned-guestrooms at this 1915 elementary school. The sizable, pink-tiled girls' restroom is now a brewery that turns out nearly half-a-million pints each year (doubles from $115; mcmenamins.com).