8 Oldest Hotels in America

The hospitality industry is booming. From hotels to bed and breakfasts, people are opening up historic properties and converting old buildings into new spaces for travelers. With the rise of digital tools like Airbnb and VRBO, travelers have more options than ever when it comes to picking a place to stay.

But with so many options, do you know which hotels stand out as the oldest in America?

Hotels aren’t just places to rest your head for the night; they’re often historical landmarks in their own right. Many hotels are known for their beautiful architecture, old world charm, and even ghost stories.

Whether you’re looking for a cozy or a grand hotel, there are plenty of old inns waiting for you in every corner of the country.

From New England to the Midwest and everywhere in-between, these are the eight oldest hotels in America.

8. The Red Lion Inn

photo source: Booking

Over 200 years have passed since The Red Lion Inn first opened its doors. In the sleepy Massachusetts town of Stockbridge, Silas Pepoon built a small tavern on the corner of Main Street and erected a red lion as its sign in 1773.

The townsfolk rallied there a year later to oppose the Acts of Intolerance imposed on the American colonies and to boycott English products.

Mr. and Mrs. Charles Plumb, who were noted for their remarkable collection of colonial antiquities, bought the inn in 1873. They were ardent collectors of excellent and rare objects.

In spite of the building’s being destroyed by fire in 1896, a wonderful collection of artifacts was kept, and many of them are still on exhibit today.

Did You Know?

Visitors may enjoy New England cuisine in the Main Dining Room at the Red Lion before relaxing with a drink by the fire in the bar, the Lion’s Den.

7. The Omni Homestead Resort

photo source: Tripadvisor

Since Captain Thomas Bullitt initially built this great dane in Virginia’s Allegheny Mountains as an 18-room inn in the middle of the 18th century, it has been welcoming visitors. Over the years, the hotel saw a number of ownership changes as it grew.

There have been 23 presidents who have been there, most famously Thomas Jefferson, who spent three weeks relaxing in the natural hot springs.

The modern hotel offers a wide range of entertainment options for guests. While ice skating and tubing are available in the winter, summer activities include tennis, zip lining, fly fishing, horseback riding, kayaking, mountain biking, and falconry.

There are swimming pools both indoors and out, as well as a sizable water park with slides and a lazy river.

Did You Know?

The Omni is the PGA Tour’s official hotel, boasting two 18-hole golf courses.

6. Beekman Arms and Delamater Inn

photo source: beekmandelamaterinn.com

The Beekman Arms and Delamater Inn is one of the oldest continuously operated hotels in the United States, having first opened their doors in 1766.

Located in the heart of the Hudson Valley in Rhinebeck, New York, the inn has a long and storied history, having hosted everyone from George Washington to Marilyn Monroe.

Today, the Beekman Arms and Delamater Inn continue to welcome guests from all over the world, offering a unique and historic lodging experience. The inn was originally built as two separate establishments – the Beekman Arms and the Delamater House. The two buildings were merged into one in 1802.

The Beekman Arms and Delamater Inn is said to be haunted by the ghost of Eliza Jumel, who was once married to Aaron Burr. The inn was used as a filming location for the TV show “Mad Men.”

Did You Know?

The Beekman Arms and Delamater Inn have been featured in numerous films and TV shows over the years, including “The American President,” “Scent of a Woman,” and “The Man in the Iron Mask.”

5. John Rutledge House Inn

photo source: artfoodhome.com

The John Rutledge House Inn in Charleston was created in 1763 by John Rutledge, who also served as South Carolina’s governor and the Supreme Court’s interim chief justice.

Rutledge is a well-known singer in the U.S. In the second-floor drawing room, the first drafts of the US Constitution were even written.

The house underwent its initial renovation in 1853, adding elaborate parquet flooring and Italian marble fireplaces, and it was later converted into an inn in 1989.

The John Rutledge, which is situated on historic Broad Street in Charleston, is close to both the Heyward-Washington House and the Old Exchange & Provost Dungeon.

Did You Know?

A long-standing custom at the hotel is to serve port, sherry, and brandy throughout the evenings.

4. Kelley House of Martha’s Vineyard

photo source: thekellyhousehotel.com

The Kelley House has welcomed guests to Edgartown, on the Massachusetts island of Martha’s Vineyard, since 1742. It is surrounded by thick elm trees and residences built by nineteenth-century whaling captains.

The inn had numerous name changes, including Marcy Tavern and Vineyard House, before being shut down in 1878. Mrs. Elizabeth A.

Kelley and her husband, William Kelley, then reopened the inn as the Seaview House and then the Kelley House in 1891.

Judges, statesmen, generals, and other well-known people of the day frequented the hotel for its pleasant ambiance and to hear Bill Kelley’s tales.

The Kelley House on Martha’s Vineyard continued to be a well-liked destination even after Mr. Kelley passed away in 1907 and Mrs. Kelley passed away in 1935. It has since stayed in the family.

Did You Know?

There are four distinct structures from which visitors can select, and all suites provide complimentary warm cookies and milk at night (served in the main lobby at the Garden House).

3. Historic Inns of Annapolis

photo source: Tripadvisor

Three structures make up the Historic Inns of Annapolis, including the Maryland Inn, where delegates to the 1783–1784 U.S.

The Governor Calvert House, originally owned by a prominent local family who resided in the home from 1727 until the American Revolution.

This also included the Robert Johnson House, which housed members of the Johnson family who were prominent city and state government officials from the 1770s to the 1800s, were the places where Congress stayed when George Washington resigned as Commander in Chief of the Continental Army and ratified the Treaty of Paris.

The three buildings, which combine Victorian grandeur and modern luxury, are all situated in the downtown historic district.

Did You Know?

One of the highlights of this place is that the guest rooms offer a good view of the state capital.

2. Concord’s Colonial Inn

photo source: Wikipedia

The Revolutionary War was officially launched in 1775 from Concord, which is arguably most known for its crucial role in ensuring America’s freedom. From here, farmers and militiamen gathered to confront the invading British forces.

Dr. Timothy Minot Jr. resided and worked on the western side of the structure, which is now the Inn’s Liberty Restaurant, around the time of the war.

On April 19, 1775, Dr. Minot welcomed the injured Minutemen inside his home to get medical attention.

He utilized one of his bedrooms, now known as “Room 24,” as an operating room and the Liberty Room as a hospital (guest room 24 is now famous for its ghost sightings).

Did You Know?

Famous visitors throughout the years have included J.P. During the years when he attended Harvard, Henry David Thoreau, Morgan, Franklin D. Roosevelt, and others all lived in this area.

1. Hotel El Convento

photo source: Conde Nast Traveler

The Hotel El Convento, which bears its name from its more than 365-year-old beginnings as a Carmelite monastery, is considered the oldest hotel in America.

The hotel is a stunning specimen of Spanish Colonial architecture and is located in the center of Old San Juan. Old-fashioned and opulent, the public areas have black-and-white checkered flooring, ornately carved wood doors, and antique furniture.

In the middle of the restaurant, Patio del Nispero, a century-old Nispero fruit tree keeps watch over patrons enjoying potent Puerto Rican coffee.

The 58 guest rooms include brilliant textiles, carved chairs and headboards, and Andalusian tile floors, making them as lively as the neighborhood’s multicolored row buildings.

Did You Know?

The nearby ancient fort, Castillo San Felipe del Morro, the San Juan Cathedral, and the hotel’s rooftop with its tiny plunge pool are all great places to cool down after a day of exploring Old San Juan’s shops and cafés.