Top 10 Most Legendary Hotels in New York City

New York City’s best and most legendary luxury hotel stays, from the iconic Plaza to the historic Knickerbocker to the infamous Hotel Chelsea.

Last updated: March 2023

There are hotels in New York and then there are New York hotels. The latter fall into an elite class of fabled, time-tested locales boasting unparalleled luxury, service, amenities and in some…secrets and scandal. Above all? An enigmatic aura conjuring up the days of nostalgic New York.

Here, we’ve rounded up 10 legendary hotels offering just that: a truly unforgettable stay in a piece of quintessential New York City history.

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The Best, Most Legendary, Iconic and Historic Hotels in NYC / Twell Magazine / www.twellmagazine.com — The Plaza / Photo by Kevin Kaminski

The Plaza Hotel

Is there a hotel more synonymous with New York City than The Plaza? Arguably not. Since opening its doors in 1907 this Manhattan landmark has been hosting distinguished guests, opulent affairs and Hollywood icons alike at its prestigious Central Park South-meets-5th Ave address.

The illustrious hotel has witnessed everything from The Beatles’ stateside arrival to Truman Capote’s Black & White Ball, the filming of The Way We Were, Home Alone 2 and The Great Gatsby and the residency of legends Marlene Dietrich, Frank Lloyd Wright and one beloved six year-old by the name of Eloise. In 1980, The Plaza was even added to the New York State Register of Historic Places.

Whether checking into one of the property’s elegant guest rooms, luxurious suites or signature Legacy Suites, taking afternoon tea at The Palm Court or sipping a glass of bubbly at The Champagne Bar, you’re guaranteed an exceptional stay in this historic New York haven.

Book your stay at The Plaza Hotel.

The Knickerbocker Hotel

Built by real estate tycoon John Jacob Astor IV in 1906, this legendary beaux-arts style hotel was the place to see and be seen at the turn of the century. Famed for lavish parties in its elegant barroom – then named “The 42nd Street Country Club – the storied Times Square setting also played host to notable residents like novelist F. Scott Fitzgerald, screen star Mary Pickford and Metropolitan Opera singer Enrico Caruso. Rumor even has it the famed martini cocktail was created here.

Along came prohibition which promptly halted not only The Knick’s glamorous affairs, but the hotel’s operation altogether in 1920. The following year the site assumed new life as the office-brimmed Knickerbocker Building; later named a New York City landmark in 1988. Fast forward to 2015 and the history-riddled property reopened as a luxury, five-star hotel.

Today, The Knickerbocker counts 330 refined rooms, all equipped with premium bed linens, Diptyque bath amenities and 24-hour room service. For a truly nostalgic stay you can check into one of four signature suites paying homage to the property’s past, like the Martini (pictured above) or Caruso Suites. The St. Cloud Rooftop Bar further boasts wraparound Times Square vistas, including a coveted view of the New Year’s Eve ball drop.

Fun fact: “Knickerbocker” refers to the original Dutch settlers who arrived to New York in the 1600s. Specifically, their pants. They rolled up just below the knee and became known as “knickerbockers” or “knickers.”

Book your stay at The Knickerbocker Hotel.

Hotel Chelsea

An imperishable ghost ship of storied hallways, venerable guests and even infamous deaths, Hotel Chelsea has been a magnet for all things legendary since its opening in 1884. The iconic 12-story facade, a blend of Queen Anne Revival and Victorian Gothic architecture, was intentionally designed by French-American architect Philip Hubert as an incubator for the arts.

Century-old walls tell tales of creativity, eccentricity and scandal alike. Mark Twain, Jackson Pollack, Dylan Thomas, Janis Joplin, Bob Dylan, Andy Warhol, Betsey Johnson and Madonna are just some of the famed guest-residents who have contributed to the bohemian enclave’s legacy…not to mention Sid Vicious, who stabbed girlfriend Nancy Spungen to death in 1978 in room #100.

Shuttered in 2011 while embroiled in ownership changeovers and controversy, the former artists’ colony – a New York City landmark since 1966 – quietly reopened just this past March. A limited number of restored guest rooms are currently on offer while the property completes renovation. Travelers of intrigue can choose from the 800-square foot One Bedroom Pied-à-Terre to the 1700 square foot Deluxe Two Bedroom Pied-à-Terre, the latter complete with 2 1/2 marble bathrooms, soaking tub, skyline views and even an in-suite Bosch washer and dryer.

Book your stay at Hotel Chelsea.

The Carlyle, a Rosewood Hotel

On the polished Upper East Side, white glove service at The Carlyle is offered at such a level of discretion to have earned the prestigious property the nickname “The Palace of Secrets. The renowned luxury hotel, named in honor of British essayist Thomas Carlyle, has famously remained a pinnacle of sophistication, glamour and privacy since its 1930 debut.

A rich history of visitors counts the who’s who of royals, world leaders, Hollywood legends and pop culture icons, including Princess Diana, every American president since Truman, Michael Jackson and even Steve Jobs. Not to mention Marilyn Monroe, who allegedly navigated a series of secret tunnels before arriving to the 34th floor suite of newly inaugurated JFK in 1961.

Exquisitely decorated rooms and lavish suites take the form of Upper East Side pieds-à-terre, some equipped with residential-style amenities and others offering sweeping Central Park and Manhattan skyline views.

At nostalgic Café Carlyle – where the sultry sounds of Eartha Kitt once wafted through the banquette-lined room – guests can enjoy a signature supper club experience set to modern-day cabaret acts like Judy Collins, Alan Cumming and John Pizzarelli. Take afternoon tea in The Gallery, or sip a Manhattan at historic hideaway Bemelmans Bar – home to whimsical murals by illustrator and author Ludwig Bemelman (whom you might know from his Madeline children’s books).

Book your stay at The Carlyle.

Waldorf Astoria New York

Even though this New York City stalwart is temporarily closed for renovation, it would be sacrilege not to include the Waldorf Astoria on this list. An icon of Park Avenue, it wasn’t always located here. The original property was built between 1893 and 1897 as two separate yet connected hotels – The Waldorf and The Astoria – on 5th Ave and 33rd Street. The hoteliers? William Waldorf Astor (The Waldorf) and cousin John Jacob Astor IV (The Astoria).

Designed for and frequented by New York’s upper crust as well as prominent foreign visitors, the opulent hotel was the first to offer complete electricity and private, en-suite bathrooms, not to mention telephones in every room and first class room service. In 1929, the property was sold to – and later demolished by – the developers of the Empire State Building.

As New York society moved further uptown, so did the hotel. In 1931, now in the hands of hotelier Lucius M. Boomer, the new Waldorf Astoria opened on Park Avenue between 49th and 50th Streets. At the time it was the largest and tallest hotel in the world, gaining international renown for its glamorous dinner parties, fundraising galas and historic conferences attended by members of the social and political elite.

Alongside such prominent figures as Winston Churchill, the Duke and Duchess of Windsor, Ella Fitzgerald, Grace Kelly, Zsa Zsa Gabor, Pope Paul VI, Frank Sinatra and countless American presidents, the Art Deco landmark has also played host to important events like the Big Four Conference (1946), Hollywood’s Communist-banning Waldorf Statement (1947), the annual April in Paris Ball (1950s) and even the purchase of four Dead Sea Scrolls for Israel (1954). Hilton Hotels Corporation purchased the property in 1972 which, in 1993, was named an official New York City landmark. Got all that?

Fast forward to 2017 and the hotel, in addition to its storied dining and drinking spaces – Peacock Alley, The Bull and Bear Steak House, La Chine and Sir Harry’s Bar – closed for extensive renovations. A makeover to the tune of $1 billion+ in fact, granting a contemporary reboot while honoring the property’s fabled past – including the preservation of legacy objects like former resident Cole Porter’s 1907 Steinway piano and the hotel’s signature 19th-century lobby clock, commissioned by Queen Victoria in 1893 for the world’s fair in Chicago. The latest incarnation of the Waldorf Astoria is slated to open in early 2023, boasting 375 luxury rooms and suites alongside 375 exclusive private residences…starting at a cool $1.8 million.

Book your (2023) stay at Waldorf Astoria New York.

Algonquin Hotel

One of the first luxury hotels in Times Square, The Algonquin – named after the native Algonquian tribes who originally inhabited the area – opened in 1902 to quickly become known as a literary refuge. In 1919 the 12-story high-rise hosted the first Algonquin Round Table, a progressive incubator where prominent writers, thinkers and theatrics gathered to exchange ideas over lunch. Met with such success the Round Table continued almost daily for nearly a decade. Vanity Fair originals Dorothy Parker, Robert Benchley and Robert E. Sherwood were among the esteemed circle’s core cognoscenti, as was Harold Ross, who founded The New Yorker after winning a lucrative poker game against other Round Table literati in 1925. All hotel guests receive free copies to this day.

With its long legacy of trailblazing, it comes as no surprise the hotel was even the first to offer rooms in New York City to solo female travelers. Or that, in the 1930s, it took in a stray cat. The fortunate feline was originally named Rusty and later named (by actor John Barrymore) Hamlet, the first of many to have strutted the halls of The Algonquin. Currently you can find Long Island rescue Hamlet VIII taking up residence in the storied hotel.

In 1987 the property was designated a New York City landmark and in 1996, a National Literary Landmark. Just like Douglas Fairbanks, William Faulkner and Maya Angelou, you too can rest – and write – in any of the Midtown sanctuary’s 181 guest rooms and suites. Fittingly, all feature comfortable work desks, not to mention elegant decor reflecting the property’s beaux-arts heritage.

Now part of Marriott’s Autograph Collection brand, checking into The Algonquin means a transportive stay in a time-honored symbol of class, culture and literary legacy. Plus, the opportunity to order a $10,000 martini at the venerable Blue Bar.

Book your stay at Algonquin Hotel.

Hotel Elysée

Founded in 1926 by Swiss-born Max Haering, this heritage hotel was originally designed as European-style lodging for the carriage trade. In 1937, nightclub hatcheck mogul Mayer Quain purchased the property out of Depression-era bankruptcy for $473,000 – whose children fancifully decorated every room so that no two were exactly alike. Instead of numbers, rooms were given characteristic names. The “Sayonara” suite payed homage to Marlon Brando’s starring role in Teahouse of the August Moon. In the “Sunset” suite, illustrious playwright Tennessee Williams took up residence for fifteen years…and took his last breath. Rumor has it his ghost still wanders the halls.

Appropriately, Life described the property as a “a swank version of a theatrical boardinghouse.” Ava Gardner was even been spotted sunbathing on her Elysée terrace. The hotel is just as famed for its 1940s-era piano bar, The Monkey Bar. Featuring a wraparound hand-painted monkey mural by caricaturist Charlie Vella, later extended with 8 more monkeys by artist Diana Voyentzie, the curious characters are there as a playful reminder that drinking can, arguably, lead to making a monkey of oneself.

Now a Library Collection Hotel, the property offers a nostalgic stay more reminiscent of the French countryside than bustling New York City. Elegant rooms and suites range from deluxe to presidential, while Elysée’s guest-only Club Room acts as a glamorous all-day living room offering gratis refreshments morning through night.

Book your stay at Hotel Elysée.

The St. Regis New York

Founded by John Jacob Astor IV in 1904 – two years before he built the aforementioned Knickerbocker Hotel and eight years before he met his fate on the doomed Titanic – this 5th Avenue icon has seamlessly retained its regal legacy since its inception. The 20-story, beaux arts-style hotel has hosted such luminaries as Salvador Dalí, Nikola Tesla, Marlene Dietrich and Alfred Hitchcock, who stayed in “his favorite” 5th floor suite at least a dozen times.

Not just notable guests, The St. Regis is also renowned for its stately King Cole Bar. Here, the modern Bloody Mary was created by barman Fernan Petiot in 1934, while Maxfield Parrish’s iconic “Old King Cole” painting hangs watchfully above the bar. The historic hotel was declared a New York City Landmark in 1988.

Now owned by Marriott, the property’s fabled white gloved staff still attend to every guest need just as they did over a century ago. All guests – regardless of room type – can take advantage of the hotel’s hallmark St. Regis Butler Service, where unpacking and packing services, newspaper and nighttime reading delivery, in-room coffee and tea service, garment pressing and more are available at your whim.

Effectively transporting guests to a bygone era of unabashed luxury, 171 rooms and 67 suites count flawless furnishings like crystal Waterford chandeliers, silk wall coverings and ornate beveled mirrors. For those seeking the ultimate in luxury – the exquisitely appointed Dior, Milano and Bentley Designer Suites await.

Book your stay at The St. Regis New York.

Washington Square Hotel

Originally opened as the 8-story Hotel Earle in 1902, this Greenwich Village gem grew to its current state of 150 rooms across 9 floors by 1917. Following a change in ownership, the property was renamed to the Washington Square Hotel in 1986. But not before the legendary downtown hideaway – perched right on the corner of Washington Square Park – saw such literary greats as Ernest Hemingway, who checked in for a 3-week stay prior to serving in WWI as an ambulance driver, and Maeve Brennan, who happened to be the first woman columnist for The New Yorker under the pseudonym “The Long-Winded Lady.” Not to mention rock & roll icons Bob Dylan, Dee Dee Ramone, Chuck Berry, John & Michelle Phillips and The Rolling Stones.

Now, the family owned and operated hotel welcomes modern-day creatives, rebels and bohemians to experience a piece of history in the heart of the Village. Nostalgic rooms range from cozy Doubles to Penthouse Kings with Washington Square Park views, all featuring polished hardwood floors, Art-Deco styled furnishings and C.O. Bigelow bath amenities. Don’t miss the Rooftop Garden, a hidden oasis serving up seasonal organic fare from it’s classic downstairs bistro, North Square Restaurant.

Book your stay at Washington Square Hotel.

Hotel Edison

This Times Square treasure opened in 1931 when Thomas Edison himself turned on the storied hotel’s glimmering marquee lights. The property continues to pay homage to its Jazz Age roots, featuring Art Deco nostalgia and vintage glamour at every turn. An established magnet for theater stars, Hollywood icons and music greats, Hotel Edison’s stylish interiors have even set the stage for such films as The Naked City, The Godfather and Birdman.

In the early 1950s, big band legend “Glorious” Gloria Parker and her orchestra hosted an evening radio broadcast at the hotel. Legendary piano bar The Rum House continues to await with live jazz music, libations and one of the city’s most expansive selections of the namesake sugarcane spirit.

Now part of Triumph Hotel group, checking in today means staying in a piece of celebrated art deco history. Rooms and suites offer a restful escape from the city’s bustling theater district, offering everything from Frette linens and robes to marble baths, private terraces and kitchenettes. Plus, in-room dining from on-site American eatery Friedman’s, complimentary NYC walking tours and a generous 1pm check-out.

Book your stay at Hotel Edison.