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 8. Frederick 9. Monterey Bay

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 22 through December 24, 2025, 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 14, 2025 through January 1, 2026. 

Where to stay: The Rittenhouse, an opulent Forbes Four-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 24, 2025 – March 1, 2026), 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 13–December 24, 2025) 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 2–31, 2025) is decidedly smaller, though no less impressive. Shop gourmet goodies and home decor from NYC’s own, followed by a stroll through Central Park.

Over in Brooklyn, the Wallabout Wonderland Holiday Market (December 6–7, 2025) transforms the Brooklyn Navy Yard into a festive maker’s haven. Expect more than 150 vendors tucked into a historic industrial space, where handcrafted gifts, artisanal foods, and live music fill the air.

Where to stay: For easy access to all the holiday happenings, opt for 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.

Across the river, Brooklyn brings its own charm. Stay at NU Hotel for an artsy, laid-back vibe near Boerum Hill and Cobble Hill, or check into The Tillary Hotel, where modern style meets easy access to the Brooklyn Bridge and DUMBO’s twinkling holiday scene.

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 5–6, 2025), 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 5–7 & December 10-23, 2025) 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 returns for its 21st edition with fresh energy and more than 115 vendors. Find it on F Street NW between 7th and 9th in Penn Quarter-Chinatown, running November 21 – December 23, 2025.

Meanwhile, the brand-new DC Holiday Market in Dupont Circle (November 14–December 23, 2025) 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 offers tailored wellness programs and a new rooftop bar and restaurant led by celebrity chef Marcus Samuelsson.

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 Holiday Market Presented by Constant Contact (November 7 – December 28, 2025). The District’s merry market will showcase 125+ 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 28–December 28, 2025), 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!)

Where to stay:  Soak in waterfront views from your room at The Envoy Hotel, an art-loving hotel in the Seaport District, where you can enjoy festive Christmas dining and a family‑friendly New Year’s Eve countdown. For an urban escape in the heart of historic Boston, check out The Whitney Hotel.

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 annual Christmas Fair fundraiser (October 31 – November 2, 2025), 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, consistently ranked as one of the best American cities to visit during the holidays. 

Shoppers should mark their calendars for Midnight Madness (first three Thursdays in December), 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 13 & December 18-21, 2025), 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: Annapolis Waterfront Hotel is a nautical retreat with unspoiled views of Chesapeake Bay, offering an exclusive holiday package that includes savings on accommodations, two Rudolph Crush cocktails, and late check-out. 

Frederick

Nestled in the heart of Maryland’s countryside, Frederick transforms into a storybook destination during the holiday season. The city’s historic streets shimmer with twinkling lights, while festive markets bring local makers, artists, and culinary favorites together for some of the region’s best holiday shopping.

Kick off the season at the Maryland Christmas Show (November 21–23 & November 28–30, 2025) at the Frederick Fairgrounds, a beloved tradition featuring hundreds of artisans and specialty vendors offering handcrafted gifts, home décor, and gourmet treats.

Downtown Frederick also hosts December Saturdays, a monthlong celebration with late-night shopping, fire pits for marshmallow roasting, and carolers weaving through the city’s historic storefronts.

At Visitation Hotel, there’s a festive highlight you won’t want to miss. The Community Market takes place on Sunday, December 7, 2025. The hotel ballroom will come alive with pop-ups from local shops offering artisanal goods, holiday treasures, and thoughtful gifts. Guests can enjoy drinks and light bites from Wye Oak Tavern while exploring.

Where to stay: Located in the heart of downtown Frederick, Visitation Hotel offers refined comfort and effortless access to the city’s holiday happenings. Step outside and you’re just moments from the festive glow of Carroll Creek and the season’s most charming markets.

Monterey Bay

There’s a special kind of holiday magic on the California coast, and the Monterey Bay region brings it to life with artisan markets, ocean views, and local character.

At The Sanctuary Beach Resort, the festivities begin right on the property with the Artisan Fair happening December 6–7, 2025. Discover handcrafted gifts and decor, sip hot cocoa or mulled wine from Salt Wood Kitchen & Oysterette, and let the kids enjoy seaside‑inspired ornament making and meet friendly goats and horses from Chaparral Ranch Marina.

Just a short drive away, the annual Christmas on the Wharf at Old Fisherman’s Wharf (December 5–21, 2025) fills the bayfront with twinkling lights, seasonal treats, and local vendors selling gifts by the sea.

For another festive outing, the Winter Wonderfest Monterey at the Monterey County Fair & Event Center offers family‑friendly fun across select dates between November 22 – December 28, 2025.

Where to stay: Retreat to The Sanctuary Beach Resort itself, a beachfront escape where cozy cottages and holiday shopping happens just steps from your door.

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!