Unwrap the Season: Festive Highlights & Holiday Events From Standout Hotels

As the holiday season approaches, a selection of standout hotels and resorts across the Caribbean and the U.S. are transforming into festive escapes designed to help travelers trade winter chills for warm-weather cheer.

From tropical tree-lighting ceremonies and beachfront New Year’s Eve celebrations to elaborate décor, immersive pop-ups, family-friendly traditions, and gourmet holiday feasts, each property is offering its own spirited twist on the season.

Whether guests are seeking a sun-soaked holiday retreat, a festively over-the-top city stay, or a luxurious winter wonderland with a coastal backdrop, these destinations deliver memorable ways to celebrate.

Whoville Hideout & Skyline Celebrations | Washington D.C.

Located steps from the National Christmas Tree and the National Monument, Hotel Washington goes all out for the holidays with over-the-top décor, from staircases draped in garland to caroling in the lobby and even a life-size Grinch. Guests can book the festive Whoville Hideout Suite (available November 22 to December 26) complete with themed bedding, a Christmas tree, holiday DVD classics, family-friendly books, homemade cookies, and mugs for cocoa or spiked eggnog, making it the quirkiest holiday stay in the capital. For a celebratory nightcap, guests can head up to VUE Rooftop for sweeping city views, festive seasonal bites and creative cocktails—the ultimate toast to the season above the skyline.

The Broadmoor | Colorado Springs, Colorado

Each winter, The Broadmoor transforms into a storybook setting of holiday wonder, where twinkling lights, towering Christmas trees, and festive décor fill the resort with seasonal cheer. The centerpiece of the celebration is the resort’s life-sized gingerbread display—a beloved Broadmoor tradition that unveils a new theme each year, crafted entirely from real gingerbread, icing, and candy, and often inspired by the property’s history or whimsical holiday tales. Guests can immerse themselves in the season’s spirit through The Broadmoor’s Twelve Days of Christmas celebration, offering daily themed activities like baking classes, whiskey tastings, candle-making workshops, and fireside story time with Mrs. Claus. The festivities continue with the Classic Broadmoor Holiday Show, a dazzling dinner-and-performance event featuring Broadway-caliber talent, as well as Breakfast with Santa, the indulgent Christmas Day Brunch in Broadmoor Hall, and a glamorous New Year’s Eve Gala and Bash. From the scent of freshly baked gingerbread to the glow of the resort’s iconic lights, every detail at The Broadmoor captures the magic and timeless elegance of the holidays.

The St. Regis Atlanta | Atlanta, GA

This holiday season, The St. Regis Atlantawill showcase festive programming and an exciting partnership for the 2025 season! Another spectacular tree collaboration with luxury fashion brand Mink, the return of The Astor Chalet, Santa Tuck-Ins, holiday cocktails, shopping experiences, an over-the-top spa offer, and more give luminaries countless reasons to celebrate the holidays at Atlanta’s Best Address.
Tradition Lives on with The Astor Chalet
- For its fifth year in collaboration with Buckhead staple, Lucy’s Market, The Astor Chalet returns. The holiday pop-up offers guests an incredible selection of festive gifts, stocking stuffers, food & wine and home décor right in the lobby.
Tea with Santa & Santa Tuck Ins
- Beginning Nov. 28 through select dates in December, guests can enjoy the celebrated tradition of Tea with Santa. The experience includes hand-selected teas, seasonal treats and live music, alongside a visit from Santa. Families staying in suites also have the option of booking a special Santa Tuck-In. And new this year, Santa by the Fire will allow guests to roast marshmallows, build delicious s’mores and share holiday wishes with Father Christmas.
24K Gilded Glamour Face and Body Ritual
- The Spa at The St. Regis Atlanta presents a luxurious holiday spa package available from mid-November through December. The 24K Gilded Glamour Face and Body ritual is an opulent body ritual drenched in collagen, gold and peptides. Skin is awakened with a dry brush exfoliation, then enveloped in a hydrating gold serum and 24-karat brightening cream for a cashmere-soft glow. The hands, feet, neck and décolleté are lavishly treated with gold collagen masks, leaving every contour replenished and radiant. This package includes a KNESKO Skin Repair Discovery Kit with a gemstone roller, full face, eye and lip masks, featuring 24K gold for at-home indulgence.
Holiday’s at The National, Autograph Collection| Oklahoma City, OK
- The National, Autograph Collection transforms into Oklahoma City’s most magical holiday destination. From early November through January, the landmark hotel becomes a storybook Christmas escape, complete with 12-foot nutcrackers, extravagant décor, and its signature Great Christmas Tree Lighting in the opulent Great Hall on November 28^th. To get in the holiday spirit, guests can indulge in the hotel’s beloved holiday tea service, ’Tis the TEAson, featuring themed teas like Elf on the Shelf, A Christmas Story, Fairytale Tea, and a Nutcracker-inspired Ballerina Tea on select weekends. Adults can sneak away to Vixen’s Vault, the moody speakeasy inside an original bank vault on property, for seasonal cocktails and live music. Festive dining is also available at on-site outlets including Tellers and Stock & Bond, with special Christmas Eve, Christmas Day, and New Year’s Eve menus. From Breakfast with Santa, a pop-up bar, a cozy winter getaway, The National offers a classic yet fresh holiday experience—all in the heart of Oklahoma City.

Dasher’s Den at Colcord Hotel | Oklahoma City, OK

Colcord Hotel invites guests to uncover a hidden gem in the heart of downtown OKC this holiday season at Dasher’s Den, a festive pop-up speakeasy tucked away on the hotel’s third floor behind what seemingly feels like a regular hotel room door. However, what was once a simple storage room transforms each holiday season into a warm, twinkling holiday hideaway decorated with candy cane pillows and shimmering baubles and feels straight out of a Christmas movie. Guests who purchase tickets to enter Dasher’s Den will check in at the front desk and receive a keychain to enter the speakeasy and are then guided upstairs to this magical hideaway, where seasonal cocktails, sweet treats, and a festive, cozy ambiance await. Inspired by a desire to surprise and delight, Dasher’s Den captures the joy of discovery and the nostalgia of the holidays for travelers.

The St. Regis Chicago | Chicago, Illinois

This holiday season, The St. Regis Chicago is unveiling details of its upcoming holiday programming, which will be unveiled through bespoke holiday experiences, blending the property’s timeless traditions with locally inspired programming.

The St. Regis Holiday Atelier: Transforming the lobby into a luxurious winter sanctuary, The St. Regis Chicago invites guests to immerse themselves in The St. Regis Holiday Atelier, a refined, experiential pop-up boutique. Reflecting the brand’s worldly elegance and flair for the exquisite, this shoppable experience celebrates the spirit of Chicago with glamorous decor and exclusive finds, featuring gifts, decor, bespoke branded items by Berlin-based brand Tom Àdam, beanies from Love Your Melon, and more.

12 Days of Sabrage: The third annual 12 Days of Sabrage will take place each evening at 5:30 p.m. from December 10-21 in The St. Regis Holiday Atelier, inviting guests to experience the art of champagne sabering, a storied ritual at The St. Regis hotels worldwide dating back to 1904. Guests and locals alike will come together as special nightly guests of honor step into the spotlight to perform this timeless ritual. Expect Chicago-based actors, journalists, tastemakers, TV hosts and more, who will raise a glass to the holidays adding a sparkling touch to the season’s celebrations. On December 20 and 21, the holiday’s most festive fellow, Santa Claus, will lead the Sabrage.

Seasonal Wellness at The St. Regis Spa Chicago: Guests can unwind in Chicago’s only Forbes Five-Star Spa, featuring bespoke treatments, a heated indoor pool, and panoramic views of the city. While on December 4, guests participate in the spa’s signature ticketed immersive Floating Pool Meditation & Sound Bath Experience, titled The Cold Moon, designed to encourage reflection and inner peace during the holiday season, allowing guests to enter the holiday season refreshed.

Family Traditions & The Astor Treasure Chest: Families visiting Chicago can enjoy their Family Traditions Package, designed to make each stay both festive and effortless. The package includes daily breakfast for four, monogrammed children’s robes, a festive welcome amenity, and a seasonal itinerary of family-friendly activities. At the heart of the experience is the Astor Treasure Chest, a whimsical trove filled with board games, books, sweet treats, and surprises—encouraging families to create unforgettable memories.

Giving Back: The St. Regis Chicago continues its partnership with nonprofit Cradles to Crayons®, with coat drop-off boxes in the lobby and donations made on behalf of each 12 Days of Sabrage guest of honor.

Sheraton Puerto Rico Resort & Casino | San Juan, Puerto Rico

This season, Sheraton Puerto Rico Resort & Casino invites guests to celebrate with a series of festive culinary experiences that highlight locally inspired cuisine, blending the rich flavors and diverse cultural influences that define the island of Puerto Rico. The holiday lineup includes a Thanksgiving, Christmas Eve, and New Year’s Eve buffets, as well as the Nikkei New Year’s Eve Six-Course Dinner & Countdown Event, blending an elevated take on how to celebrate the New Year. Expect seasonal décor, along with on-site activations from a Coquito Class (Dec. 13 + 27), and Live Local Music every Friday and Saturday leading up to Christmas, and much more!

Aloft San Juan | San Juan, Puerto Rico

At Aloft San Juan, the holidays kick off on November 21 with their “Let’s Christmas Shine at Aloft”, where guests can expect a lively tree-lighting celebration complete with cocktails, music, and a pet-friendly atmosphere, allowing travelers to celebrate with their furry loved ones. Throughout December, the property will begin to host a Social Wednesday with festive themes, along with a Holiday Pop-Up Market – December 16 and 17 – spotlighting local artisans, and the Vive el Sunset Coquito Fest on December 21, offering poolside coquito tastings and live beats. Seasonal cocktails under the Winter Sips & Wonder menu round out the celebrations, making Aloft San Juan, a vibrant social hub for the holidays.

The Westin Puntacana Resort & Club | Dominican Republic

The festive season begins early at The Westin Puntacana Resort & Club with a Christmas Lighting Ceremony on November 4 at The Village Puntacana, followed by the Lucky Turkey Tennis & Padel Tournament on November 29 and a Christmas Bazaar on December 6, featuring local crafts and culinary delights. Families can enjoy festive traditions like the Gingerbread House Opening on December 16, or tennis lovers can enjoy the holiday tournaments at the Oscar de la Renta Tennis Center from December 26–29. The season culminates with a New Year’s Eve Gala Dinner and Celebration – where they can expect an elevated culinary offering with live music!

The St. Regis Cap Cana | Dominican Republic

At The St. Regis Cap Cana, guests can look forward to the resort’s first festive season, blending Caribbean charm, local traditions, and refined luxury. The property will come alive with sparkling décor, live entertainment, and curated seasonal programming designed for both couples and families. Guests can indulge in gourmet holiday feasts, sun-soaked beachfront gatherings, New Year’s Eve celebrations, and restorative wellness rituals at the Iridium Spa. Children and teens can enjoy festive workshops and family activities, while adults savor cocktail hours, curated wine dinners, and poolside soirées—all set against the stunning backdrop of Cap Cana’s pristine shores.

The Ritz-Carlton, Grand Cayman | Cayman Islands

At The Ritz-Carlton, Grand Cayman, the holiday season is filled with festive experiences from Pie-Making Workshops with Executive Pastry Chef Camilla Testa, witnessing the grand Gingerbread House Unveiling on December 9, or joining in the Festive Cookie Decorating Sessions throughout Christmas week, along with Holiday Caroling on December 24. Expect elevated dining experiences on Thanksgiving and Christmas Day – from lavish feasts to chef-prepared meals to-go. While New Year’s Eve offers Michelin-level tasting menus to beachfront parties and fireworks on Seven Mile Beach.

Salterra, a Luxury Collection Resort & Spa, South Caicos | Turks & Caicos

Guests can expect a blend of local island traditions with refined celebrations from daily wellness rituals, culinary workshops, curated tastings, and much more! Guests can attend their signature events from a Tree Lighting Ceremony, Christmas Eve Gala Dinner, and celebrate entering the New year with their New Year’s Eve Celebration within the Lucari Ballroom. Guests are invited to enjoy the Yuletide Carol Gathering with Marjorie Basden High School choir, a local school within South Caicos, and a community gift drive.

The Ritz-Carlton, St. Thomas | U.S. Virgin Islands

The Ritz-Carlton, St. Thomas ushers in the holidays with a full lineup of festivities, beginning with Thanksgiving Weekend dining across their signature venues, including beachfront barbecues, Italian-inspired dinners, Caribbean feasts, and a Thanksgiving Parade featuring Moko Jumbies and steel pan music. Families can experience the holiday festivities by participating in the Ritz-Carlton Elf Hunt from December 17-25, along with festive dinners throughout the season, and expect cabana experiences. The celebrations culminate on New Year’s Eve with an All-White Countdown Carnival featuring DJs, fire dancers, and a chance to enter a future three-night stay giveaway!

Event Name

bread & Butter

Website

https://www.wearebreadandbutter.com/