New York

Ducks, Docks, Detention: 9 Unique Hotels Worth The Trip

Some people look for luxury when they book a hotel, others want something quaint.

Then there are those who turn to trusty chains where they can build up their points and status. But for those who value experiences over things, vacations are a way to encounter something new and completely unexpected.

For this subset of traveler looking to break out of their comfort zone, these non-traditional places to rest your head are as quirky as can be. Ranging from schools to boats, museums, and even insane asylums, the weirder the venue, the more memorable the getaway.

McMenamins Kennedy School – Portland, OR


No More School, No More Books, No More Teacher’s Dirty Looks. You’re certainly not alone if Diane De Groat’s children’s favorite brings back memories. Most children can’t wait to escape their four-walled prison come summer, yet somehow parents are finding their way back to the classroom. McMenamins Kennedy School operated as an elementary school from 1915-1975, eventually shuttering due to declining enrollment. As a community-gathering place for 60-some years, neighbors fought tooth and nail to keep the building from being condemned.

The city eventually approved the proposal to turn the elementary school into a hotel and the quirky building was given a new lease on life. The premise is you can fall asleep in class, have a whiskey in detention and run through the hallways without any sort of principal or disciplinarian to scold you. The former classrooms have been converted into guestrooms without losing charming touches like chalkboard walls and cloakrooms. The English wing overlooking the courtyard is even literary-inspired, an ideal reprieve for book nerds and bibliophiles. The A+ amenities include an auditorium/movie theater, which plays cult classic classics, a soaking pool, bikes to rent (because… Portland), and even an on-site brewery (also because… Portland).

McMenamins Kennedy School

9.2 Excellent (766 reviews)

Madonna Inn – San Luis Obispo, California


A landmark property on historic Route 101, the Madonna Inn is 240-miles south of San Francisco and 200 miles north of Los Angeles. With virtually no other attractions in the area, it has become the major tourist draw. Despite having no overarching theme, each room is a stand-alone marvel from the Love Nest to the Golfer’s Haven. The property has been featured in everything from The Bachelor to a handful of music videos. It’s been mentioned in a Weird Al Yankovic song and even inspired an episode of The Simpsons.

First opened in 1958 with 12 rooms, a terrible fire in 1966 shuttered the property. Lucky for us, the rebuild was even gaudier. Rooms are themed every which way from pioneers and deserts to cars and queens. The Caveman room is one of the most popular, but the four rock rooms also book out months in advance. The first woman to sleep in all 110 rooms took seven years and completed the challenge in 1977. Several others have since finished the feat. If you swing by, don’t miss their most famous feature – a rock waterfall urinal created by Hollywood set designer Harvey Allen Warren. Girls have been known to sneak into the men’s room to snap a photo, so make sure you bring a friend to guard the door.

Madonna Inn

Top rated
San Luis Obispo
9.2 Excellent (2475 reviews)

Queen Mary – Long Beach, California

In her heyday, the Queen Mary was the grandest ocean liner ever built and an unthinkable luxury during the Great Depression. Heeding the call of duty, she was transformed from passenger ship to warship, aiding the allied forces in their time of need and then converted back again. She set sail for the last time in 1966 as the commercial airline industry took off. Larger and faster than the Titanic, a number of celebrities and dignitaries have graced her presence from Audrey Hepburn and Elizabeth Taylor to Queen Elizabeth and the Kennedys.

Today, the Queen sits docked in Long Beach, allowing passengers to spend the night (if you dare) or tour the ship without having to worry about getting sea legs. Notoriously one of the most haunted places in the US, the ship offers a number of ghost tours from “Dining with the Spirits” to paranormal investigations. The staterooms are appointed with their original art deco touches from the ‘30s and 50s. Over 50 types of wood are used for intricate carvings and finishes. While the décor is grand, the exhibits are even grander, celebrating the likes of Winston Churchill, Princess Diana, and of course, the Titanic.

The Queen Mary

Long Beach
8.1 Very good (3118 reviews)

The Liberty – Boston, Massachusetts


Constructed in 1851 as Charles Street Jail, the penitentiary has housed a number of (in)famous characters throughout its lifetime, perhaps most notably Malcom X. Declared in violation of inmates’ constitutional rights, it shuttered in the ‘70s due to poor living conditions. The 298 rooms have since been transformed from barebones cell blocks to the utmost in luxury. A national historic landmark, The Liberty retained its cell doors, bars, and catwalks as an ode to its former life.

While the building pays homage to its sordid past, the only real jailhouse touches in the rooms themselves are playful; “solitary” do not disturb signs. If the thought of sleeping in a prison gives you the heebie-jeebies, you can rest easy knowing a team of Buddhist monks cleansed the space before it reopened to the public. Bad juju begone.

The Liberty, a Luxury Collection Hotel, Boston

Top rated
8.8 Excellent (2119 reviews)

The Red Caboose Motel – Ronks, Pennsylvania


Believe it or not, The Red Caboose Motel was born out of a dare. Way back in 1969, the founder bid on nineteen 25-ton N-5 cabooses from an auction held by the Pennsylvania railroad. Soon after, he became the proud owner of 475 tons of steel. And what else to do with used train cars than to open a train-themed motel? Those 19 cars have since expanded into 38 with a collection that includes a variety of shapes, sizes, layouts, and floor plans.

Beyond the trains themselves, the property offers a hodgepodge of eccentric attractions. Free movies are shown in the barn out back, there’s a retro nickelodeon player, a quarter arcade, Amish buggy rides, a silo viewing tower, and a petting zoo complete with mini ponies, alpaca, and a potbelly pig. It’s also minutes away from the National Toy Train Museum and the Railroad Museum of Pennsylvania so you can geek out about the rails all the livelong day.

Red Caboose Motel & Restaurant

Top rated
9.0 Excellent (2083 reviews)

21c Museum Hotel – Louisville, Kentucky


The first hotel of it’s kind; 21c Museum Hotel is a multi-venue contemporary art museum housed in a converted tobacco and bourbon warehouse. The hotel features over 9,000 square feet of exhibition space with art that spans centuries including a double life-sized David. The museum is free of charge and open to the public 24 hours a day, seven days a week with docent-led tours twice weekly.

The rooms are designed to feel artsy yet approachable, like a well-appointed apartment you could come home to. Listed on the National Register of Historic Places, the concept caught on and they’ve since expanded to nine additional cities across the U.S.

21c Museum Hotel Louisville

Top rated
9.4 Excellent (2150 reviews)

The Peabody – Memphis, Tennessee


Despite being a Forbes Four-Star and AAA Four-Diamond hotel, The Peabody’s most famous guests are their ducks. A tradition that started back in the ‘30s, the GM had just returned from a hunting trip and found it amusing to leave three of his feathered friends in the hotel fountain. The guests fell in love with the Mallards and they’ve been a mainstay ever since. The ducks have appeared on the Late Show, the Oprah Show, and even graced the pages of People magazine.

In a serendipitous turn of events, their bellman at the time doubled as a circus trainer and assumed the ever-important job of “Duckmaster.” Every day for 50 years, he marched the ducks from their penthouse palace on the roof (that cost $200,000 to build) down to the red carpet in the lobby as a crowd of fascinated onlookers gawked in delight. Celebrities also delight in becoming temporary duckmasters with A-listers like Kevin Bacon and Molly Ringwald taking a turn at the coveted title.

Peabody Memphis

Top rated
9.3 Excellent (407 reviews)

Hotel Henry – Buffalo, New York


Long travel days can make anyone feel a bit loopy, which is why Hotel Henry might be a suitable reprieve.

Formerly the Buffalo State insane asylum, this beautiful boutique property was a collaboration between the best designers of the time from the Central Park landscape team to the Dean of Architecture at Yale.

A big part of the mental health facility’s philosophy was providing ample access to the outdoors, which hasn’t changed for hotel guests. Situated on 42-acres of land, they call themselves an urban resort with easy access to open-air cafes, a cultural corridor, and sweeping park grounds. But there are rumors of the property being haunted by former patients so stay alert for what goes bump in the night.

The Richardson Hotel

Top rated
9.2 Excellent (1603 reviews)

The Vintages – Dayton, Oregon


Generally, a trailer park resort would be considered the opposite of haute luxury, but The Vintages is the very definition of shabby chic. Each of the 13 trailers (in all shapes, sizes, and colors) has their own meticulously manicured lawn that looks like Pleasantville brought to life. Think cul-de-sac in the suburbs, with an irony that makes it a hipster haven. The 14-acre property resides in the heart of Willamette Wine Country with amenities to match. Pour over coffee, cruiser bikes, and terry cloth robes await.

The Vintages Trailer Resort

Top rated
9.2 Excellent (474 reviews)