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24 Last-Minute, Cheap Winter Vacation Deals to Book for 2020

If you're looking for an amazing—and affordable—place to go this winter, you'll love these budget-friendly travel deals you can book ASAP.

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cheap winter vacations, best winter vacations, winter vacation ideascourtesy Sonesta Resorts Sint Maarten

Cheap winter vacation in the Caribbean

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Happily, the half Dutch/half French Caribbean jewel is up and running after the devastation wrought by Hurricane Irma in 2017. Indeed, the first major hotel brand to welcome guests was the Sonesta on the Dutch side. For travel between December 19, 2019, and January 6, 2020, the Unwrap Your Holiday Special offers 35 percent off at both the adults-only, all-inclusive, ultra-luxe Sonesta Ocean Point, as well as at its family-friendly, all-inclusive sister property, Sonesta Maho Beach Resort, Casino and Spa. (Pre-discount, rates start at $335 nightly per person at Ocean Point and $225 nightly per person at Maho Beach.) Both properties are on the Dutch side (St. Maarten), and festivities include brunch and beach-barbecue specials, five-course dinner specials, entertainment, and plenty of Santa! Book before November 30, 2019, for travel during the aforementioned dates, and use the promo code HOLIDAY. Want a cheap flight to match this great discount? Here's how to use Google Flights to save big.

cheap winter vacations, best winter vacations, winter vacation ideascourtesy Woodloch Resort

Cheap winter vacation in the Poconos

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Named the #1 Family Resort in America by Trip Advisor, the all-inclusive Woodloch Pines is nestled in the heart of Pennsylvania's Poconos mountains and overlooks Little Teedyuskung Lake. While Woodloch is a four-seasons resort, winter is arguably the most magical time with a sledding hill (readied for action with snow guns if the weather isn't cooperating), two skating rinks, ice fishing, ice hockey, and the Woodloch Winter Olympics with "competitions" in tubing, sliding, rolling, and more. Or you can choose to relax indoors at the resort's world-class spa. Rates start at $209 per person, and the promo code FAMILY will net you 15 percent off from early November through December 22, 2019. During these "Olde Fashioned Holiday Weekends in the Poconos," you'll enjoy reindeer races, Christmas caroling, a holiday scavenger hunt, eggnog, cookies, and a visit from the white bearded gent in red! Speaking of the big man himself, don't miss these stories about meeting Santa that will fill you with the Christmas spirit.

cheap winter vacations, best winter vacations, winter vacation ideasvia tripadvisor.com

Cheap winter vacation in Cleveland

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This may surprise you, but if you're into serious gastronomy and charming locals, Cleveland is the place to head this year. Plus, flights from around the country are inexpensive, met by even more affordable hotel rates. You'll be treated to savory meals from celebrity chef Michael Symon, beautiful local scenery, and luxury accommodations at the Ritz-Carlton. The hotel’s "Be a Rock Star" package offers the ultimate experience, pairing a stay at the plush Ritz-Carlton with a visit to the Rock and Roll Hall of Fame, turndown service, and complimentary cocktails at TURN Bar + Kitchen starting at $339 per night. If you're looking for a true escape, check out this list of the country's least-crowded winter destinations.

cheap winter vacations, best winter vacations, winter vacation ideasvia tripadvisor.com

Cheap winter vacation in New York City

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If you've been waiting for the perfect time to check out New York City and enjoy the lights, shopping, Broadway shows, and world-class dining (at locally famous eateries like Mastro's, Reserve Cut steakhouse, and the Instagram-famous Dough Doughnut), the start of the new year will be a dream come true. Pod Hotels is offering a major savings deal—one of our best last-minute travel deals—that is perfect for city lovers. Rates at Pod 39 and Pod 51, both in Midtown, start at just $79 per night in January and February. New York may be one of the most expensive cities to live in, but while you're out and about, there are plenty of free things to do in New York City.

cheap winter vacations, best winter vacations, winter vacation ideascourtesy Park Hyatt St. Kitts

Cheap winter vacation in St. Kitts

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Through December 21, 2019, the Park Hyatt St. Kitts is offering guests a fourth night free—plus a $300 resort credit. All of their rooms and suites face the turquoise water of Banana Bay and include a spa-inspired bath. We can already hear the birds chirping and feel the sand between our toes. Here are some more great warm-weather destinations to escape the cold.

cheap winter vacations, best winter vacations, winter vacation ideasvia tripadvisor.com

Cheap winter vacation in Vermont

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Local New Englanders and New York–area vacationers will revel in a discounted midweek stay at the Lodge at Spruce Peak in Stowe, Vermont, where top-of-the-line, ultra-luxe accommodations will be discounted to rates as low as $200 per night in January and February. If you're not already an avid snow bunny, a stay at this Stowe resort will turn you into one. That said, there are plenty of other things to enjoy there as well, including a top-notch spa and dining scene. Stowe also made our list of destinations that are even better in winter.

cheap winter vacations, best winter vacations, winter vacation ideasvia tripadvisor.com

Cheap winter vacation in Cancun

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If you're looking for an especially quiet (read: no kids allowed) tropical resort, Haven Riviera Cancun is what you're looking for. They’re offering up to 50 percent off their regular rates redeemable for travel between December 21, 2019, and January 2, 20020. This is one of our favorite last-minute travel deals because you've got so much time to use it. Pack your things, darling—you're about to see some sunshine. Cancun isn't the only place you can visit in Mexico, make sure you explore other popular destinations in Mexico while you're there!

cheap winter vacations, best winter vacations, winter vacation ideasvia tripadvisor.com

Cheap winter vacation in Austin

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If you've been meaning to hit up Texas’ ever-trendy Austin area, this winter is the right time. Book deluxe accommodations for three nights at Lakeway Resort and Spa and the third night is half off. It's the perfect blend of access to the great outdoors—offering boating, fishing, and miles of lake shoreline—and has bustling Austin nearby. Austin also happens to be one of the best places in America to have a girls' weekend away.

cheap winter vacations, best winter vacations, winter vacation ideasvia tripadvisor.com

Cheap winter vacation in Orlando

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If hitting major theme parks is high on your list this winter, the last-minute travel deals we found in the Orlando area will be especially exciting to you. The Grove Resort & Spa Orlando is offering rates from $199 per night on a two- or three-bedroom suite; this special booking also comes with a Star Wars-themed welcome bag, $25 daily resort credit, a round of mini-golf, and more. The resort even offers a free shuttle back and forth to Disney grounds. This deal is bookable through December 19, 2019, so don’t delay. Here are some more great winter getaways for families that won't break the bank.

cheap winter vacations, best winter vacations, winter vacation ideasvia tripadvisor.com

Cheap winter vacation in the Ozarks

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If you're a nature-lover and can't get enough of that woodsy scent, you'll want to head straight to Big Cedar Lodge in the Ozark Mountains of Missouri. The area boasts an Ancient Ozarks Natural History Museum, the 18,000-square-foot Cedar Creek Spa, and a nature-based heritage preserve perched on a majestic cliff top, Top of the Rock. Big Cedar Lodge is offering a “Happy Holidays Package” starting at $174—replete with a Christmas photo session, Sleigh Bell Scurry family scavenger hunt, personalized Christmas gift for the whole family, and more. Make sure you pack your hiking gear, the Ozarks are also home to one of the best hikes in America.

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