Winter travel inspiration: Find your perfect seasonal stay
Find the perfect winter escape and explore these top destinations for holiday magic while keeping your budget in check.
By Alina Dizik | November 13, 2025
Finding joy in the holiday season means making space for celebrations and connections. And if you’re traveling, hopefully it also means doing so without stress. For a winter getaway that truly feels like a vacation, it matters where you stay. Luckily, we’ve got you covered with all the right amenities and holiday sales that will help you stay on budget during this special time of year. Sneak in some much-needed downtime at these top winter destinations for a memorable seasonal stay.
New York
New York City shines even brighter come wintertime. Staying at Hampton Inn by Hilton New York Times Square puts you in the center of it all for your winter vacation, with plenty of holiday flare nearby. You can walk to the Rockefeller Center Christmas Tree or twirl around its famous ice-skating rink, then browse the shop windows along Fifth Avenue, or enjoy the Radio City Rockettes at their legendary venue. And with major subway stops nearby, navigating the city is simple. Back at the hotel, enjoy hot breakfast daily, creative cocktails at the Interlude Rooftop Lounge, and modern connecting rooms to make family travel easier. Best of all: Hilton Honors Members can get up to 17% off the best available rate, allowing you to stretch your Big Apple budget and spend more on adventures.
Toronto
With holiday pop-ups, winter lights displays, and plenty of rinks to lace up your ice skates at, Toronto is a winter wonderland that takes the holiday season seriously. Hilton Toronto makes for a festive and elegant home base, with well-appointed guest rooms within walking distance of Osgoode Station, the famous Royal Ontario Museum, and the iconic CN Tower. The hotel is also connected to Toronto’s Downtown Underground Pedestrian Walkway (the PATH) so you can navigate around the city without enduring blustery temps during the winter months. When it’s time to relax, soak in the hotel’s indoor-outdoor pool, which is heated and open all year. Don’t forget to try a seasonal cocktail or a meal at Frenchy Bar et Brasserie, the French-inspired lobby bar and lounge where guests and locals linger.
Chicago
There’s plenty to see in the Windy City during the holiday season. You’ll find European-inspired Christkindlmarket stalls, holiday shows, and some of the country’s best museums during your winter urban escape. Stay at Hampton Inn & Suites Chicago Downtown to be close to all of the festivities. Complimentary breakfast, a Digital Key in the Hilton Honors app, and pet-friendly rooms leave you with more time to explore without worrying about logistics. Shop the nearby Magnificent Mile or wander the halls of the Art Institute of Chicago. Take a break to skate in Millennium Park with views of The Bean, the city’s famous mirrored Cloud Gate sculpture. Don’t miss the Tiffany-stained glass dome at the Chicago Cultural Center, which offers free admission and is right across the street from the park. Afterward, warm up with classic Italian cuisine, including house-made pastas and hand-stretched pizza, at the hotel’s trattoria, Olio E Piu.
Orlando, Florida
If you’d rather trade snow for sun-soaked holiday parades, family-friendly theme parks, and plenty of palm trees, Orlando is the ultimate holiday destination. Combine that with a hotel like Spark by Hilton Orlando near SeaWorld and you’ve got the ideal formula for both relaxation and excitement. You’ll be just minutes from SeaWorld, Aquatica, and Discovery Cove, plus a short drive to other popular theme parks, where the whole family can spot their favorite characters. Plus, Spark’s budget-friendly yet stylish accommodations save room in your budget for fun activities and seasonal experiences, while on-site parking and Confirmed Connecting Rooms by Hilton™ make it easy to regroup between outings. Taking a break at the hotel? You’ll strike the perfect balance of downtime and adventure with the outdoor pool, free breakfast, and flexible workspace.
Alina Dizik
Alina Dizik is a veteran lifestyle journalist, covering travel, real estate, family, work trends, and dining. She lives in Chicago and has previously lived in New York, Europe, and the Middle East. She spends more than two months each year traveling internationally with her husband and two school-age children. Alina has visited more than 50 countries, and her work appears in The Wall Street Journal, BBC, The Cut, The Guardian, and other top publications.
Save up to 25% during The Hilton Sale
Whether you’re craving a cozy city break or the thrill of somewhere new, find the perfect holiday stay in top destinations across the United States, Canada, Mexico, and more. Book November 5 through December 15, 2025.
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