Step Back to the 1920s With Vintage Photos of New York’s Grand Hotels

When we think of 1920s New York, images of glitz, glamour, and grandeur come to mind. The city’s iconic hotels stood as towering symbols of luxury during this golden age, hosting celebrities, business tycoons, and international royalty.

These magnificent buildings weren’t just places to stay; they were social hubs where history was made and the pulse of Jazz Age New York beat strongest.

1. The Waldorf Astoria: Symbol of Manhattan Elegance

Rising 47 stories above Park Avenue, the Waldorf Astoria defined luxury accommodation in 1920s New York. Originally two separate hotels built by feuding members of the Astor family, they merged in 1897 before relocating to their iconic Park Avenue address in 1931.

The hotel’s famous Art Deco interiors featured gleaming marble floors, gilded ceilings, and custom furnishings that attracted the era’s elite. President Herbert Hoover called it home, while celebrities like Charlie Chaplin and Al Jolson were regular guests.

The Waldorf’s legendary ballroom hosted the most exclusive social gatherings of the decade, while its kitchens birthed culinary classics like Waldorf salad and Eggs Benedict. Its innovative room service concept forever changed hotel operations worldwide.

2. Hotel Pennsylvania: A Landmark Across From Penn Station

Strategically positioned across from Pennsylvania Station, Hotel Pennsylvania opened its doors in 1919 as the world’s largest hotel with 2,200 rooms. The McKim, Mead & White architectural firm designed this magnificent structure with a grand facade that stretched an entire city block.

The hotel’s famous phone number, Pennsylvania 6-5000, inspired Glenn Miller’s iconic swing tune and remains one of the oldest continuously used phone numbers in New York. Inside, the Café Rouge ballroom became a premier jazz venue where Benny Goodman and Count Basie performed for dancing crowds.

Famous guests included presidents, movie stars, and world leaders who appreciated its perfect location and first-class amenities. The hotel’s swimming pool was considered an engineering marvel, while its barbershop served 14,000 customers weekly during peak times.

3. The Plaza Hotel: Fifth Avenue’s Crown Jewel of the Jazz Age

Standing majestically at the corner of Fifth Avenue and Central Park South, The Plaza Hotel embodied the pinnacle of 1920s opulence. F. Scott Fitzgerald immortalized this 19-story French Renaissance château-style masterpiece in his literature, most notably in The Great Gatsby.

Wealthy guests arrived in chauffeur-driven Rolls-Royces to stay in lavish suites featuring gold-plated fixtures, silk wallpaper, and crystal chandeliers. The Palm Court, with its stained-glass ceiling and afternoon tea service, became the place for high society to see and be seen.

Silent film stars like Clara Bow and Rudolph Valentino frequented The Plaza, while financial titans conducted business deals in its ornate meeting rooms. The hotel’s legendary Oak Room bar operated as a speakeasy during Prohibition, serving illegal cocktails in teacups to its well-connected patrons.

4. The Biltmore Hotel: Grand Central’s Hidden Luxury Spot

Connected directly to Grand Central Terminal via an underground passage, The Biltmore Hotel welcomed travelers in supreme style after its 1913 opening. This 26-story Warren & Wetmore creation became famous for its magnificent clock in the lobby, where countless New Yorkers arranged to meet “under the clock at The Biltmore.”

The Biltmore’s Cascades Roof nightclub emerged as one of Manhattan’s hottest Jazz Age venues. Flappers danced until dawn while orchestra bands played the latest hits under a ceiling painted to resemble a star-filled sky.

Hollywood royalty stayed in its presidential suites, including silent film stars Mary Pickford and Douglas Fairbanks. The hotel’s innovative amenities included ice water on tap in every room and a special ladies-only floor with female staff. Its famous Billiard Room hosted high-stakes games among Wall Street’s elite throughout the Roaring Twenties.

5. The Roosevelt Hotel: A 1920s Icon With Timeless Style

Opening its doors in 1924, The Roosevelt Hotel became an instant landmark on Madison Avenue. Named after President Theodore Roosevelt, this Italian Renaissance-style building featured 1,025 rooms that quickly became the preferred choice for politicians and business leaders.

The Roosevelt’s magnificent lobby dazzled visitors with its terrazzo floors, marble columns, and intricate plasterwork. Guy Lombardo and his Royal Canadians began performing at the hotel in 1929, broadcasting their New Year’s Eve celebrations nationwide and popularizing “Auld Lang Syne” as a holiday tradition.

The hotel’s Madison Club Lounge operated as a speakeasy during Prohibition years, with secret panels hiding liquor bottles during police raids. The Roosevelt’s rooftop garden provided a glamorous escape for dancing under the stars, while its barber shop offered haircuts to Manhattan’s most powerful men.

6. The Commodore Hotel: Modern Luxury in Its Day

Constructed as part of Terminal City, the massive development surrounding Grand Central Terminal, The Commodore Hotel opened in 1919 with great fanfare. Named after “Commodore” Cornelius Vanderbilt, this 2,000-room colossus featured the latest technological marvels including circulating ice water and a state-of-the-art ventilation system.

The Commodore’s Century Room quickly gained fame as one of New York’s premier ballrooms. Tommy Dorsey and his orchestra held court here, while society events filled its calendar throughout the Roaring Twenties. Presidents Calvin Coolidge and Herbert Hoover stayed here during official visits to New York.

The hotel’s innovative services included a theater ticket office, telegraph station, and fully staffed medical clinic for guests. Its barbershop employed 42 barbers working in shifts, while the Grand Ballroom hosted elaborate fashion shows featuring Parisian designs for New York’s elite female shoppers.

7. The Algonquin Hotel: Literary Legends and Lasting Charm

Much smaller than its towering contemporaries but equally significant, The Algonquin Hotel opened in 1902 and reached cultural prominence in the 1920s as home to the famous Round Table. This daily gathering of writers, critics and wits included Dorothy Parker, Robert Benchley, and Alexander Woollcott, who exchanged barbed commentary over lengthy lunches.

The hotel’s Oak Room became a cabaret showcase where musical talents performed intimate shows for appreciative audiences. The Algonquin’s first owner, Frank Case, established its literary reputation by offering free accommodations to struggling writers who later became famous.

A succession of feline residents known as Hamlet lived in the lobby, a tradition that continues today. While lacking the grand ballrooms of larger hotels, The Algonquin compensated with intellectual atmosphere and personal service that attracted cultural luminaries from across America and Europe throughout the Jazz Age.