Twinkling lights, handmade ornaments, ice skating rinks in the middle of the city. Few places bring out holiday cheer like a good old-fashioned holiday market. These winter wonderlands originated in Europe, but you don’t need a passport for an authentic experience. From D.C. to San Diego, cities and towns across America have kept tradition alive with their own unique holiday markets infused with local flair. 

Luckily for guests of Independent Collection Hotels & Resorts, some of the best holiday markets are right outside our doorstep. Discover our top picks for wintery destinations with amazing holiday markets for the whole family.

Table of Contents 1. Philadelphia 2. New York City 3. San Diego 4. Washington, DC 5. Boston 6. El Paso 7. Annapolis

Philadelphia

Rich with history and high-drama architecture, Philadelphia’s City Hall is a magnificent backdrop to the city’s largest holiday markets. 

The iconic Christmas Village in LOVE Park draws from German tradition for a month-long celebration marked by German arts and crafts, steamy mulled wine, stein-holding contests, and live performances by German artists and musicians. Running November 23 through December 24, the sprawling market also features a double-decker carousel, a Ferris wheel, storybook readings, and other family-friendly happenings; not to mention, more than 100 vendors from all over the world including Käthe Wohlfahrt, a famous German Christmas store that sells glass ornaments, birdhouses, and other traditional gifts made by German artisans.

Nearby at Dilworth Park, the annual Made in Philadelphia market has even more holiday shopping, crafted and curated by local artisans from Philadelphia and the surrounding Tri-State area. Admission is free to this local favorite, running November 15, 2024 through January 1, 2025. 

Where to stay: The Rittenhouse, an opulent Forbes Five-Star hotel and MICHELIN Key awardee, is located within walking distance of all the excitement and history Philadelphia has to offer. Retire from an exhilarating day of sightseeing with a cup of hot cocoa in the lobby, tuck into a sumptuous meal at Lacroix or Scarpetta, or slip into the cozy comfort of Library Bar for a seasonal cocktail.

New York City

New York City is an epicenter of holiday spirit, from the Macy’s Thanksgiving Day Parade to New Year’s Eve in Times Square, to famous holiday markets in Manhattan. 

Bryant Park in Midtown draws thousands of holiday revelers for its famous Winter Village (October 25, 2024 – March 2, 2025), an all-ages event that’s practically bursting with activities. Join an ice skating class; après skate with rinkside cocktails; cozy up in a private igloo; try your hand at curling; or challenge your friends to a bumper car race on ice! (Pro tip: Make your reservations in advance online.)

Across town at Union Square, you’ll find a funkier market focused on local vendors selling everything from vinyl records to mosaic lamps and hand-made jewelry. Named one of the best holiday markets in America in 2023, the Union Square Market (November 16–December 24) is surrounded by award-winning restaurants, perfect for a pit stop when you’ve had all the strudel you can stomach.

Another European-style market, the Columbus Circle Holiday Market (December 3–31) is decidedly smaller, though no less impressive. Shop gourmet goodies and home decor from NYC’s own, followed by a stroll through Central Park.

Where to stay:  For easy access to all the holiday happenings, opt for the Aliz Hotel Times Square, home to one of the highest open-air bars in Manhattan. Over in Midtown East, the glamorous Hotel 48LEX offers sophisticated luxury with residential-style suites perfect for couples and families.

San Diego

A cultural hub of San Diego, Balboa Park is a massive 1,200-acre green space, home to some of the city’s best museums, historic landmarks, botanical gardens, and the iconic San Diego Zoo. 

Plan your visit around December Nights at Balboa Park (December 6–7), an annual holiday festival with culinary pop-ups, Santa Claus sightings, and a dedicated family zone with STEAM activities. December Nights is the city’s largest free event of the year, with big entertainment to match. After the ceremonial tree lighting, catch live performances by over 1,200 local artists including poetry and skateboarding demos, plus retail goodies from local vendors.

At another cultural landmark, Little Italy will host a festive version of its weekly Wednesday market throughout December, spotlighting local purveyors and San Diego artisans. Stroll through the historic neighborhood, then grab a bite to eat at one of many Italian restaurants nearby.

The Petco Park Holiday Market (December 5–27) is a relative newcomer that takes place in Gallagher Square, adjacent to the San Diego Padres stadium. Pose for your holiday greeting card amid the winter light display; sip on cinnamon-dusted cider; share your wish list with Santa Claus; and get up close to real-life reindeer! 

Where to stay:  Carté Hotel is centered in the heart of the action, steps from Little Italy, the San Diego Bay, and exciting Downtown adventures.

Washington, D.C.

There’s something for everyone in Dupont Circle: indie bookstores, boutique shops, salsa dancing, cool museums, and an improv club! Even more to love, the historic D.C. neighborhood will feature two new holiday markets this year. 

A familiar favorite, the DowntownDC Holiday Market will shake things up for its 20th anniversary with a new management team, larger space, and more vendor shops than ever before. Check it out in the Penn Quarter-Chinatown neighborhood from November 22 through December 23.

Meanwhile, the brand-new DC Holiday Market in Dupont Circle (November 22–December 15) will feature a smaller, more intimate experience that spotlights local businesses and boutique brands from the District, as well as D.C. DJs and local dancers.

Where to stay: Hotel Madera is a charming boutique hotel with delicious on-site dining, all within walking distance from Dupont Circle. Across town, Capitol Hill Hotel is close to Smithsonian museums and the U.S. Capitol building, perfect for history buffs. In D.C.’s NoMa neighborhood, The Morrow Hotel is a calming retreat with tailored wellness programs and a stunning rooftop lounge with sweeping skyline views.

Boston

Where much of Boston maintains colonial charm, the sleek, modern Seaport District is transforming a swath of waterfront into a cool community space unlike anywhere else in the city. Check out the scene this holiday season at Snowport. The District’s merry market will showcase 60+ small businesses from the New England area, from chocolatiers to carpenters, along with culinary pop-ups slinging raclette cheese sandwiches, hot mulled cider, and other seasonal treats served with gorgeous views of the harbor. 

Skip the mall on Black Friday and head toward the SoWa Winter Festival instead (November 29–December 22), where you’ll find an edgy indoor-outdoor marketplace full of hand-thrown ceramics, natural soaps, kitschy wall art, and other artful delights made by Boston creatives. (Pro tip: plan your visit around SoWa’s First Fridays, when gallerists and artist studios open their doors to the public!)

On the hunt for more unique gifts? Visit the Harvard Square Holiday Fair, a juried arts and crafts fair, and one of the oldest fairs in the Boston area. Mingle with local artisans as you wind through a treasure trove of welded jewelry, hand-painted pottery, and fine art prints.

Where to stay:  Soak in waterfront views from your room at The Envoy Hotel, an art-loving hotel in the Seaport District. The Boxer boasts one of the best locales in the city, walking distance to Beacon Hill, the North End, and Downtown. For an urban escape in the heart of historic Boston, check out The Whitney Hotel. Closer to Harvard Square, Freepoint Hotel Cambridge offers a chic, modern stay with a secret garden lounge.

El Paso

Looking to escape the snow? Pack your bags for the pink-hued desert landscapes of West Texas and downtown El Paso. 

Inspired by its multicultural heritage, El Paso’s holiday markets pair classic Christmas traditions with a community feel. The Junior League of El Paso will host its 51st annual Christmas Fair fundraiser (November 22–24), featuring local merchants and vendors from the Southwest region. A portion of proceeds benefit the Junior League, a women-led organization that aims to uplift the El Paso community through volunteerism and leadership training.

Another local favorite, the Upper Valley Market brings a holiday twist to its weekly event for Christmas time. Outdoors and under the sun, guests can weave through white canopies of locally sourced meats and cheeses, hand-stitched stockings, ceramics, and more.

El Paso WinterFest is the city’s largest seasonal celebration in downtown El Paso. Along with a spectacular Parade of Lights, families enjoy sledding, ice skating, holiday movie screenings, and live performances through December.

Where to stay:  An icon of El Paso’s skyline, The Plaza Hotel Pioneer Park pairs Texas history with distinct Art Deco style and MICHELIN Key service.

Annapolis

For an idyllic winter vacation, make your way to Annapolis, Maryland, voted one of the best American cities to visit during the holidays. 

Shoppers should mark their calendars for Midnight Madness, a pseudo block party and shopping event in downtown Annapolis where boutique stores stay open late for last-minute gifts.

More shopping awaits at the Annapolis Holiday Market (December 12–15), where over 120 artisans and specialty food vendors line the cobblestone streets. In between retail therapy, watch a parade of boats light up the Chesapeake Bay, join a Kwanzaa celebration, or catch a riveting theater performance.

Where to stay:  Voted one of the best Mid-Atlantic hotels by Conde Nast Traveler readers, the Annapolis Waterfront Hotel is a nautical retreat with unspoiled views of Chesapeake Bay. Plan your stay around the hotel’s Candlelight Concert series inspired by famous holiday concertos like Vivaldi’s “Four Seasons” and “The Nutcracker” by Tchaikovsky. 

Wherever you dream of traveling this winter, anchor your adventures at Independent Collection Hotels & Resorts, where local culture and one-of-a-kind experiences make for a magical holiday. Explore our boutique hotels and start planning!