Southern Hotels You Won't Want To Miss During The Holiday Season

The Cloister Lobby

Peter Frank Edwards

From dreamy decorations to themed cocktails or tea with Santa, these five hotels go all out for the season—and at some, you don’t even have to stay the night to join in on the fun.

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The Cloister at Sea Island

Christmas At The Cloister
Classic holiday finery complements The Cloister’s signature grand arches and stately lobby.

Peter Frank Edwards

Sea Island, Georgia

Make a trip to Sea Island (a private, 50-acre retreat nestled in marshes along the Atlantic), and visit The Cloister. The name conjures up hushed privacy, yet it’s a joyful place at Christmas with twinkling trees, a life-size gingerbread house, and carolers. At this almost 100-year-old gem of the Golden Isles, you can escape the season’s rush. It’s a gift to relax amid the grandeur of the Mediterranean-style design by architect Addison Mizner—known for his work in Palm Beach, Florida. From the main lobby, with row upon row of dramatic arches and columns, to the red-tile roof and lush courtyards, you’ll experience peace amid all the usual bustle. Guests have the option to stay in suites in the Main Building near the water, the Main Building Wings with garden and river views, the Beach Club, or the Ocean Residences. With a salon and golf courses, The Cloister lures couples looking to unwind or swing a club. Book a massage or facial at the award-winning spa or a lesson at the Golf Performance Center. Families can enjoy holiday extras like a warm cookie with milk accompanied by a bedtime story with Santa’s elves, while pet owners can enter the Reindog Parade. Kids even get a gift from Santa and Mrs. Claus at the Children’s Christmas Party. To ring in the New Year, Deck the Hallways Classic holiday finery complements. The Cloister’s signature grand arches and stately lobby. Watch fireworks crackle above the beach; then brave the chilly Atlantic waves during the Polar Plunge the following morning.

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Four Seasons Resort Orlando at Walt Disney World Resort

Four Seasons Orlando
The Four Seasons Resort Orlando at Walt Disney World Resort offers a variety of photo ops and kid-friendly activities.

Courtesy of Four Seasons Resort Orlando At Walt Disney World Resort

Buena Vista, Florida

Would you trade your Mickey Mouse ears for top-notch cuisine and a Mistle-Toes pedicure? You don’t have to. Combine a family vacation to Walt Disney World with some pampering at the iconic Four Seasons. The mix of Disney fun and high-end amenities feels as magical as the sorcery in Fantasia. Hotel guests can utilize the resort’s Disney Planning Center to map out trips to the parks, but they should make time for Four Seasons activities, from the on-site Good Morning Breakfast with Goofy & His Pals to cookie decorating with the pastry chef. Send your little ones to a story time with Santa or on an elf scavenger hunt. Sample gelato in flavors like peppermint or gingerbread at Lickety Split, the lobby cafe. Concierge childcare services allow dinner for two at Capa, a Michelin-star-rated rooftop restaurant with terrace views of Disney fireworks. If a stay isn’t doable, the lobby itself is worth a visit. Snap a Christmas card picture by the breathtaking tree. It’s decked in gold and reaches toward a chandelier meant to resemble fireworks, featuring specially crafted “bursts” made of 30,000 crystal components.

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Montage Palmetto Bluff

Outside of Montage Palmetto Bluff
Montage is aglow with lights inside and out.

Courtesy of Montage Palmetto Bluff

Bluffton, South Carolina

At Montage Palmetto Bluff, you get the chance to slow down and feel immersed in yuletide cheer. Gracious Southern style pervades at this large-scale inn with an in-house spa. It’s located on the moss-draped grounds of a rustic yet sophisticated community on the South Carolina coast. Anyone can enjoy dinner at two restaurants (elegant River Side and intimate Octagon) or visit the grounds to see the decorations, gorgeous nature trails, and a pedestrian bridge lined with flickering lamps—the perfect perch for spotting shorebirds. For resort guests, the fun starts during Thanksgiving week. Activities include an oyster social, a painting class featuring the local scenery, football-watching events, and the Lighting of the Inn. Through December, families who stay at Montage canorder a gingerbread kit or take a walk through the property with a resort naturalist and add a birdseed ornament to the outdoor Christmas tree. Mrs. Claus tells stories on Saturday afternoons, and Santa invites you to brunch. Those who’ve decorated the hotel in artful greenery and accents teach a wreath-making class, while the mixologists at Hush (the resort lounge) host a gathering to share tips and pour drinks. Find family fun like bounce houses, yard games, and tunes at the outdoor Festive Frolic Frenzy event. Every night of Hanukkah, there’s a menorah lighting in the inn’s library. On Christmas Eve, live musicians play most of the day in the lobby and the May River Chapel (just across from the inn) hosts a beautiful service with carols and scripture.

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The Jefferson Hotel

The Jefferson Hotel
The Jefferson Hotel comes alive in December with hundreds of poinsettias, garlands, and lights. Don't miss admiring the ornate stained glass ceilings and the marble statue of Thomas Jefferson.

Cedric Angeles

Richmond, Virginia

From a fountain bubbling with white lights and red bows instead of water to the glimmering 30-foot tree in the Rotunda lobby, The Jefferson offers Instagram-worthy backdrops aplenty. Even if you don’t stay at this 1895 hotel, a showcase of the Beaux Arts architectural style, it’s worth a visit. Take the requisite pictures; marvel at the annual gingerbread display; or make a reservation for dinner at Lemaire Restaurant, featuring Virginia and Atlantic seafood, steaks, and locally grown produce. The hotel’s popular winter brunches serve station after station of breakfast fare, soups, seafood, and more, with tables set in the Rotunda lobby, an adjacent lounge area, and on the Mezzanine. Everyone has a good view of the tree, and a jazz trio ensures a festive vibe. After a pandemic hiatus, it’s the first year back for this annual tradition, meaning it’s best to book early. Likewise for the Holiday Afternoon Tea or the Chocolate Lover’s Tea, both served on the Mezzanine. To surprise a child with a Santa Tea (when the big guy himself appears alongside your Earl Grey and sweet treats) snag your spot as early as October. The real star of these events is the resplendent hotel itself. If you’re interested in a stay next Christmas, ask about midweek Holidays at the Jefferson packages. (Start checking the hotel website in August for information on the scheduled festivities.)

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Hotel Emma

Hotel Emma Private Dining
Hotel Emma's Christmas spirit shines in Supper's private dining room as well as cheery displays throughout the property.

Courtesy of Hotel Emma

San Antonio, Texas

Most Texans are familiar with the multicolored bulbs that dangle in loose strands over tourist boats in downtown San Antonio, but on the River Walk’s quieter Museum Reach, the luxe Hotel Emma offers a different kind of show. This historic brewhouse turned hotel overlooks trees outlined almost branch by branch in lights. They beam at the river's edge like spotlights, reflecting on the water and wowing visitors of all ages. Topped with a turret and accented by the brewery’s former smokestack, Hotel Emma’s 1894 brick building boasts Second Empire architecture and adds a sense of heritage to the city’s skyline. After meticulous renovations, it proudly presides over the restored Pearl district, which is now a hub for restaurants and boutiques. There, you’ll also find weekly Holiday Night Markets highlighting regional artisans, Posada at Pearl (a Latin American celebration that centers around the reenactment of the Holy Family’s search for lodging in Bethlehem), and a Hanukkah event with a menorah lighting. Dining options range from Pearl’s eclectic Food Hall at Bottling Department and French bistro Brasserie Mon Chou Chou to Southerleigh Fine Food & Brewery, a down-to-earth spot where beer bottles decorate the indoor tree. If you’d prefer to stay in, try the on-site restaurant Supper (an elegant eatery run by San Antonio native chef Jorge Hernández) or sip on cocktails in the cozy Sternewirth tavern, which features intimate seating inside restored beer tanks. Other culinary traditions here include Mexican hot chocolate and wedding cookies, tamales, and German stollen (a fruit-and-nut bread). Yes, be sure to check out the ever-popular lights downtown, but don’t miss Hotel Emma—your taste buds and your sense of wonder will thank you for it.

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