Couple in front of a Christmas tree in Chicago

City Guide

The Best Places in the U.S. to Visit During the Holiday Season

By Bri Hand | Oct 12, 2021

‘Tis the winter season of love, Christmas lights, and giving. So, why not give yourself a little love with a holiday season trip! 

As winter travel opens up this year, so can your winter vacation plans. There are plenty of reasons to take a trip this winter—whether you want to celebrate on the city streets, under twinkly Christmas lights, or beachside with a blazing bonfire, there’s a perfect vacation destination for your seasonal getaway. 

Whether you’re packing your bags for a solo winter trip, planning a romantic winter getaway with your significant other, or tag-teaming with your favorite furry friend, here are the best places to visit in winter across the country:

  1. Austin, Texas
  2. Chicago, Illinois
  3. Washington, D.C.
  4. West Palm Beach, Florida
  5. New Orleans, Louisiana

Let’s get started!

1. Austin, Texas

Looking for a warm winter getaway minus the beachy atmosphere? Austin, Texas, is your holiday winter destination! This notoriously hip city delivers traditional holiday activities with a unique flair and some amazing bites. Who needs snow when you’ve got incredible lights and tasty barbecue in a beautiful place? 

For a full taste of Austin’s holiday spirit, check out these attractions during your warm winter vacations:

  • Austin Trail of Lights: With over 2 million lights and 90 trees, this holiday exhibit is Austin’s longest-running holiday tradition. Thousands flock to Zilker Park each year to catch this winter wonderland’s jaw-dropping light displays, sweet snacks, and live performances. The best part? Ticket proceeds go back to community-based nonprofit organizations. Catch this winter festival anytime from Thanksgiving through early January.
  • Armadillo Christmas Bazaar: Leading right up to Christmas Day, this festive and lively Armadillo Christmas Bazaar marketplace fulfills all of your gift shopping needs. You can find everything from charming ornaments to pristine local art between its 200 vendors. Between stores, stop for some talented live music acts and delicious food (don’t miss the shawarma!).
  • Local bar scene: Austin has a renowned bar scene, with plenty of bustling spots that’ll make you feel like a local during your winter trip. Check out the whiskey wells on Rainey Street, craft beers on South First Street, or all the divey hangouts on the Eastside.
  • BBQ, BBQ, and more BBQ: No one visits Austin without tasting some local delights, especially the barbecue. Juicy, tender, and smoky, this city’s brisket and ribs are some of the best across Texas (or the entire South, for that matter). Breakfast tacos and other Tex-Mex fares should also go to the top of your list during your warm winter vacation. 

Check out Landing’s fully furnished apartments in Austin here! 

2. Chicago, Illinois

While the winter lakeside wind does make for a chilly winter season, what are the holidays without a snowflake or two? Chicago is a city that wholeheartedly celebrates winter, packed to the brim with stunning displays, excellent shopping, and festive activities.

Embrace the Midwest winter weather and gorgeous lake views with these citywide events:

  • Christkindlmarkt: If there’s one winter holiday event you must visit in Chicago during your winter travel, it’s the Christkindlmarkt. Pulling from the city’s German heritage, this market is a true replica of the traditional European Christmas market. Nosh on pretzels and gluhwein, pick up some adorable wooden toys, and explore all the gift options in each Tudor-designed stall.
  • Ice skating: One big plus for a cold-weather destination? All the amazing outdoor activities, like ice skating. Chicago offers plenty of quality rinks across the city, from Maggie Daley Park to Millennium Park to Navy Pier. Strap on your blades and take a few laps before heading inside for some hot cocoa to warm up the body.
  • Light displays: On every corner, Chicago fills its streets with holiday lights to illuminate the city’s beauty during the winter months. Start with the Lincoln Park Zoo, where you can see over 2 million lights at the ZooLights display. Then, head downtown to stroll the Magnificent Mile and catch the festive store window displays, ending with the majestic City of Chicago Tree at Millennium Park.

Check out Landing’s fully furnished apartments in Chicago here!

3. Washington, D.C.

Washington, D.C. may not traditionally sit at the top of everyone’s winter holiday getaway list, but it should! Between its patriotic traditions and killer light displays, the U.S. capital celebrates the winter months in style. And, during the cold weather months, you get to skip all the spring and summer tourist crowds. 

Take a dive into this city’s best holiday fare:

  • GLOW in Historic Georgetown: Georgetown doesn’t light up just during the holidays. This beautiful district’s art path, GLOW, displays themed light shows year-round! And in winter, you’ll see more avant-garde and experimental takes on “holiday lights,” from neon signs to glowing orbs. Take a tour before shopping at one of Georgetown’s many adorable boutiques.
  • National Christmas Tree: What’s a holiday in Washington, D.C. without lighting the National Christmas Tree? People of all ages and backgrounds can appreciate this delightful ritual, as thousands of twinkly lights spark to life in front of the White House. 
  • Downtown Holiday Market: This is your one-stop shop for all things holiday. Ornaments, toys, clothing, jewelry, food, drinks, and more are available throughout the market’s 70-plus diverse stalls. And, with different local performers every day, you’ll always have something exciting to discover.

Browse our fully furnished apartments in Washington, D.C., here! 

4. West Palm Beach, Florida

If the thought of snow makes you blue, turn the beat (and thermostat) around with a holiday in West Palm Beach. Tropical weather, luxurious homes, and some excellent ocean views make this city a year-round destination. Ride the beach vacation wave and try these winter activities in West Palm Beach:

  • Rosemary Square: Just because you’re at the beach doesn’t mean you can’t celebrate the holidays! Hop over to Rosemary Square, where West Palm Beach hosts its central holiday pop-up market. After shopping for souvenirs, explore the decorating workshops, live music, and magnificent Wishing Tree, complete with fake falling snow.
  • Florida beaches: You probably came to Florida for one big reason: beach time. While West Palm Beach technically has no beaches, it’s a hop, skip, and a jump away from some sandy shores. Take the Intercoastal Waterway to the island of Palm Beach, or drive out to Jupiter Beach, Juno Beach, or Lake Worth Beach.
  • Sandi Land: At the center of Sandi Land lies Sandi, the 35-foot holiday “sand tree” made entirely of Palm Beach sand. This holiday arena pops up annually in the city’s Great Lawn, offering everything from light displays to synchronized swimming shows. 

Check out our fully furnished apartments in West Palm Beach!

5. New Orleans, Louisiana

If there’s one thing New Orleans knows how to do, it’s party. The city roars to life during the holidays, sprinkling its zany culture onto traditional events. Between the local “fetes,” rainbow lights, and downright tasty food, you’ll never run low on festive cheer in the Crescent City. 

Don’t forget to check out these holiday city must-sees:

  • Celebration in the Oaks: This lights festival has made a name for itself beyond New Orleans. Celebration in the Oaks is like a multi-colored fairyland, with glowing constructions amidst the park’s gorgeous oak trees. For an extra kick of fun, ride the century-old carousel that’s still operating.
  • LUNA Fete: Soak in the city’s creativity via LUNA Fete. Located in the central Lafayette Square, this holiday festival showcases all the artistic talent that New Orleans has to offer—all for free! Contemporary installations stand in front of the city’s historic buildings, a beautiful tribute to its artsy legacy.
  • Mississippi River bonfires: For a real New Orleans-style holiday tradition, stick around until Dec. 24. Along the Mississippi River, you can see locals stoke bonfires to light the way for “Papa Noel,” the Cajun Santa Clause. It’s the kind of rowdy, full-hearted display that only New Orleans could do. 

Check out our furnished apartments in New Orleans!

Vacation like a pro with Landing 

There’s no place like home for the holidays. And with Landing, you can feel at home just about anywhere in the country. 

If you want to take an extended trip this winter, Landing offers fully furnished apartments in over 375 cities throughout the U.S., with flexible lease terms that let you stay for as long as you’d like. And, for a limited time, you can save up to $750 on your next Landing during our Fall Promotion. Visit hellolanding.com to learn more!

About the author

Bri Hand

Bri Hand is Landing's Content Marketing Manager. She currently lives in Salem, Massachusetts, with her partner and dog, Arlo, but relishes any opportunity she can to travel so she can try new foods, see gorgeous sights, and daydream about living somewhere new after visiting there for less than 24 hours.