Sometimes we make travel plans around a list of sights to see, but sometimes, travel in the South is more of a pilgrimage, centered around a single destination. The stories these hotel lobbies could tell and the feeling of dressing up for dinner in restaurants that have hosted generations of travelers before us are reasons enough to plan your trip around your accommodations — instead of the other way around.
After a stay at any of these timeless Southern hotels, you’ll understand why they’ve welcomed guests for centuries and still continue to top travel bucket lists today. These are the hotels that families visit again and again — they become a rite of passage, a way to mark the passing of time through generations. Couples celebrate anniversaries and honeymoons. Families pass down memories. Adults remember visiting as children with their parents and grandparents, and someday, they’ll bring their own children, too.
These iconic Southern hotels are more than just places to stay. They’re traditions.
8 Iconic Southern Hotels on Our Bucket List
The Greenbrier
101 Main Street West, White Sulphur Springs, WV 24986 • (855) 453-4858
Dorothy Draper fans will find their mecca at the bright, colorful, over-the-top Greenbrier. America’s Resort, as it’s called, has entertained guests, dignitaries, and movie stars since 1778. The resort found its home in the West Virginia mountains due to the natural mineral springs that occupy the area, and now visitors can golf, dine, relax, and shop, all on the 11,000-acre property.
The resort boasts multiple restaurants and a casino, and it’s the type of place where guests dress up for dinner. In fact, jackets and formal dress are required within the main dining room for the evening meal. You’ll find activities of leisure here, including clay shooting and falconry. The experience is like stepping back in time in the most luxurious way.
SB TIP: For history buffs, there’s an added bonus beyond The Greenbrier’s two and a half centuries of existence. Carefully concealed on this genteel property is a former Congressional relocation bunker that remained hidden in plain sight for decades before it was declassified. Visitors can now embark on a 90-minute tour revealing all of the former government secrets.
Grand Hotel
17855 Scenic Hwy 98, Fairhope, AL 36532 • (251) 928-9201
Each afternoon at 3:45 p.m., a cannon rings out over Mobile Bay. It’s a resounding reminder of the Grand Hotel’s history as a Civil War-era hospital and World War II training facility, where Allied forces trained prior to the final pushes of the war. But, now, life operates at a much slower pace at this 550-acre resort on the Gulf Coast. With more than 400 renovated rooms, two golf courses, a spa, beach, and pools, this historic hotel is a wonderful place to spend time on the water and enjoy the warmth of Southern hospitality. Saddle up for a drink at 1847 and order the aptly named 1847, a refreshing take on a mint julep. This timeless bar and the other restaurants on-site have a masculine, yet sophisticated, ambiance — you may be on the beach, but you won’t find any cliché beachfront decor in sight. Plus, you’re just minutes from the charming town of Fairhope, which makes for a fun day trip of dining and shopping.
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The Jefferson Hotel
101 West Franklin Street, Richmond, VA 23220 • (804) 649-4750
Founded in 1895 in downtown Richmond, The Jefferson Hotel is the embodiment of elegance and history. And, since its earliest days, it’s been on the cutting edge of luxury, bringing modern touches like electricity and running water to guests long before these conveniences were standard in homes. Now, The Jefferson continues to deliver a top-notch experience with impeccably renovated rooms and glittering bathrooms that will make you want to unpack and stay a while.
Don’t miss the famous champagne brunch on Sundays or afternoon tea, served Friday through Sunday. For a fine dining experience, check out Lemaire, an elevated take on Southern dining. Visit at Christmas for a particularly festive experience. The Jefferson Hotel lobby fully decorated is a sight to be seen and a Richmond tradition.
The Cloister at Sea Island
100 Cloister Drive, Sea Island, GA 31561 • (855) 572-4975
The Cloister was founded in 1928 on an island off the Southern coast of Georgia, and now, almost 100 years later, the resort is one of the most famed and beloved hotels worldwide. This “friendly little hotel,” as it was first called, stands out against the Lowcountry marsh and the sweeping views of the Atlantic with its terracotta roof and Mediterranean styling. The rooms at The Cloister have a traditional, dark wood, opulence that matches the luxury of the lobby and the ballrooms. Just steps away, you’ll find casual fun in the sun at the Beach Club, as well as golf, biking, tennis, bowling, and more. In addition to The Cloister, you also have the option to stay at The Lodge, The Inn, the Cottages, or Broadfield on Sea Island.
Old Edwards Inn and Spa
445 Main St, Highlands, NC 28741 • (866) 526-8008
Dating back to 1878 when it served as a boarding house, Old Edwards Inn and Spa is now a Relais & Chateaux property and the culmination of more than a century of hospitality iterations. It is home to multiple guest accommodations, including the historic inn. There’s no “wrong” season to visit the Old Edwards Inn and Spa, with its breathtaking views of the Blue Ridge Mountains changing drastically as the months pass by (though, autumn leaves are certainly a sight to behold!). Part of the beauty of this resort is that you’re both steps away from hikes and waterfalls along the Blue Ridge Mountains and yet still in the heart of the bustling mountain town of Highlands. This is a destination that will appease both your outdoorsy mom and your city-loving sister.
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Hotel Monteleone
214 Royal Street, New Orleans, LA 70130 • (504) 523-3341Â
Since 1886, five generations of the Monteleone family have run the Hotel Monteleone, a historic hotel in the heart of the French Quarter in New Orleans. Located just a short walk from the renowned debauchery of Bourbon Street, this hotel exudes all the Southern hospitality and formality that New Orleans is known for, and its glittering lobby seems like a luxurious respite from the hot, humid streets.
While the hotel itself is a famed place to stay, what the Hotel Monteleone is perhaps best known for is The Carousel Bar. Arrive early and grab a seat at this rotating bar (hence the name). Order a classic New Orleans milk punch or a Vieux Carre, with New Orleans’ own Sazerac whiskey, and settle in for the night. They have live music most evenings — this is New Orleans, after all.
Williamsburg Inn
136 Francis Street East, Williamsburg, VA • (855) 233-1437
Williamsburg Inn is a luxury experience that comes with a side of colonial history, but regardless of whether you’re a history buff, you’ll appreciate the luxurious and traditional rooms, some named after past visitors whose faces you might recognize, Queen Elizabeth and Prince Philip among them.
You’ll find all the classic resort amenities, from golf to a pool to the spa, but the Williamsburg Inn is known for its award-winning food, which ranges from fine dining to a step back in time at Chowning’s Tavern. If you do have an interest in 17th- and 18th-century history, then you’ll love being just a few paces from Colonial Williamsburg, the College of William and Mary, and more people in colonial dress than you ever imagined you’d see in one place (if Felicity was your favorite American Girl doll, this is the place for you!).
The Breakers
One South County Road, Palm Beach, FL 33480 • (877) 964-6847
We couldn’t tick off a list of iconic Southern hotels without including The Breakers, right? Founded in 1896 by Henry M. Flagler (a name you’ll see again and again in Palm Beach), The Breakers was named, as you might imagine, for the fact its location practically kisses the sea as waves crash in front of it. Over the course of its century-and-a-quarter-long history, The Breakers has become synonymous with Palm Beach. While the island may have a few fabulous hotels on the beach now, this is still the hotel.
Enjoy a drink in the grand lobby to see and be seen. Order a Railcar #91 at HMF, named after Mr. Flagler’s private car, for a refreshing, citrusy escape. Spend your days sitting by the beach, or take up a round of golf. When in Palm Beach, life is meant to be leisurely, and The Breakers is here to provide the perfect backdrop.
Here’s to new adventures!
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