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.
Every editorial product is independently selected, though we may be compensated or receive an affiliate commission if you buy something through our links.
It’s the most wonderful time of the year—for a deal!
Got the winter blues but think it’s too late to book an affordable vacation? We’ve got some really good news for you: It’s not! Not only can you still get a flight at a discount, but you can also get some stellar last-minute hotel deals. We found the best packages for every kind of traveler and every kind of vacation—whether you’re looking to immerse yourself in the Christmas spirit in a storybook town, see the sights in a big city, or get away from it all in a tropical locale. So, what are you waiting for? These cheap winter vacations are budget-friendly and perfect for the whole family.
Cheap winter vacation to the Cape
During the holidays, rates at the iconic Chatham Bars Inn, rated #2 in Best Cape Cod Hotels by U.S. World and News Report, are slashed to $499 a night—nearly half of what it costs in summer. The winter enchantment at the Inn begins around Thanksgiving when the lobby transforms into the North Pole, complete with a life-size gingerbread house, a gingerbread replica of the town of Chatham, and Christmas trees and decorations everywhere you look. Your kids can create festive keepsakes in Santa’s workshop filled with sand and also enjoy hot chocolate. All this, plus winter bonfires on the beach! If you can’t get enough of the holiday spirit, check out the most charming old-fashioned Christmas towns in America.
Cheap winter vacation in Guadalajara
This charming city, the second-largest in Mexico, is the birthplace of mariachi music and tequila. If that’s not enough of a reason to visit, AC Hotel by Marriott Guadalajara, Mexico, named one of the coolest luxury hotels in the province by LuxuryHotelGuides.com, has rates of $102 per night. Located next to popular attractions such as the Guadalajara Cathedral, the hotel has a sky lounge, an infinity pool overlooking the city skyline, a state-of-the-art fitness center, and scrumptious Spanish and Mexican cuisine to enjoy after a hard day’s touring. And don’t miss these other cheap beach vacations to take with your family all year long.
Cheap winter vacation in Utah
If you’re hungering for a restorative and reflective end to 2019 surrounded by nature, look no further than the Red Mountain Resort nuzzled in Southern Utah’s red rock bluffs, not far from Zion National Park. From Black Friday through Cyber Monday (November 29 through December 2, 2019), the all-inclusive resort will offer $100 off per person if you book a three-night Essential Retreat, which is normally $345 per person per night. This is applicable on stays before February 28, 2020. Included are daily hikes for all skill levels; wellness, nutrition, and fitness classes; and great food. The resort, spread over 55 acres of black lava gardens and mesquite plants, has 82 rooms and 23 villa suites, pools, bikes, a meditation labyrinth, and a spa. Emerge ultra-relaxed and ready for whatever 2020 holds. If you’re taking a road trip to your destination, check out the most scenic drives in America.
Cheap winter vacation in Belize
Belize equals bliss. This small Caribbean treasure perched between Mexico and Guatemala is home to the world’s second-largest barrier reef, colossal Mayan ruins, and exotic wildlife. Just in time for the holidays, the Belize Ocean Club—a 5-star dive resort, according to the Professional Association of Diving Instructors (PADI), that’s located on a 78-mile peninsula in Southern Belize near the picturesque village of Placencia—is launching the Family Adventure Package. There is a three-night minimum stay, which includes two-bedroom suites with oversized seaside balconies, a Mayan Sky Combo with ziplining and river tubing (up to four people), and daily dinner with a bottle of wine. Guests can also enjoy the spa, gym, and a large infinity pool with a swim-up bar. Rates are $475 per room per night. However, a code exclusively for Reader’s Digest readers, RDPROMO, nets you an additional $100 off. See? Bliss! Here are more sunny islands you can book for Christmas, including a private island in Belize.
Cheap winter vacation in California
Huntington Beach, aka Surf City USA, named “the Best Beach of California” by USA Today, is blessed with 10 miles of pristine, uninterrupted coastline and year-round sunshine. An hour from tony Los Angeles, the vibe here is casual and easygoing. Think: beach bonfires, sandcastles, and lazy strolls on one of the longest piers on the West Coast. The Kimpton Shorebreak Resort is a pet-friendly seafront haven with a 40-foot-wide rock-climbing wall and “surf ambassadors,” who ensure guests have an authentic local experience. Around the holidays, the resort is offering an Outlaw the In-Laws deal. Rates start at $199 and include a welcome bottle of wine for stays from November 21, 2019, through January 12, 2020. If you want to stay closer to home, check out the best winter destinations in every state—including yours.
Cheap winter vacation in Nicaragua
Grab your chance to visit this Central American gem before it becomes as popular (and pricey) as neighboring Costa Rica. Nicaragua features the largest area of primary-growth rainforest north of the Amazon, six active volcanoes, surfing beaches, spectacular wildlife, and Spanish colonial architecture. Selvista Guesthouses—located in a virtual cloud-forest summit on the slopes of Maderas Volcano—offers housing from just $40 to $114 per night. Their adventure packages include $750 for a one-week stay with tours of Ometepe and the Corn Islands. Ometepe boasts twin volcanic peaks rising out of Lago de Nicaragua, while the two Corn Islands, 43 miles off Nicaragua’s Caribbean coast and once a refuge for pirates, is palm-fringed nirvana. Here are some more under-the-radar places to visit before they get too popular.
Cheap winter vacation in Washington D.C.
Come the holidays, you can feel the buzz of excitement in the air as the nation’s capital glows with outrageously dazzling light displays. Perhaps the biggest—not just in Washington, D.C., but in the country—is Enchant Christmas at Nationals Park, while the National Christmas Tree stands stately and resplendent on the White House Ellipse. If you want to immerse yourself in this winter wonderland for a few days, the Swann House B&B has you covered. Holiday rates for this turreted Victorian mansion circa 1883, replete with elaborately carved working fireplaces and a swimming pool, are $269 and up. But if you choose the Holiday Vacation Package, the fourth night is free from November 15 to December 31, 2019, in the Regent, Jennifer Green, Il Duomo, and Blu Sky Room; you’ll also get a complimentary bottle of wine to enjoy by the fireplace. There’s also a Winter Vacation Package, where the third night is 50 percent off. While there, regale friends and family with these wacky facts you never knew about Washington, D.C.
Cheap winter vacation in Hawaii
Aloha to the Aqua-Aston holiday deal that’s almost too good to be true. The hospitality group is offering a Cyber Monday deal of 20 percent off its 40 properties across the Hawaiian Islands if you book between December 2 and 4, 2019. At Aston Maui Hill, a 140-room condo near Wailea, you’ll be treated to dreamy ocean views, and on his big day, Santa will arrive by helicopter to the tune of—what else?—”Here comes Santa Claus.” At the Iilkai Hotel & Luxury Suites, located at the edge of Waikiki, sunset is welcomed every evening by the blowing of the conch. On New Year’s Eve, watch the fireworks from your private lanai (balcony). And yet another option is Aston at the Whaler on Kaanapali, a condo hotel rated among 2019’s 10 top hotels in Maui by LuxuryHotelGuides.com. While all of Hawaii is pretty amazing, here’s why Maui may be the best Hawaiian island.
Cheap winter vacation in Arizona
It’s easy to see why one of Santa’s favorite stops during the Christmas season is Scottsdale, Arizona. The weather is perfect, the rates are reasonable, and the Yuletide celebrations abound. That’s particularly true at the comfortable but luxe Fairmont Scottsdale Princess, which has six golf courses, six pools, and more than four million sparkling LED lights. For the holidays, this AAA Five Diamond resort features Santa’s Secret Headquarters, Princess Express Trains, a Build-A-Bear Workshop, S’mores Land, Mrs. Claus Corner, and more. The Sip, Savor & Celebrate Holiday Package runs from November 26 through December 31, 2019, and includes a $75 resort credit and up to two adult and three child passes that provide VIP Access to Christmas at the Princess attractions. Rates start at $259. By the way, here are the towns in every state that really know how to get into the Christmas spirit.
Cheap winter vacation in the Caribbean
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 vacation in the Poconos
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 vacation in Cleveland
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 vacation in New York City
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 vacation in St. Kitts
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 vacation in Vermont
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 vacation in Cancun
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 vacation in Austin
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 vacation in Orlando
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 vacation in the Ozarks
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.
Cheap winter vacation in North Carolina
If you love a good patriotic, all-American holiday gift, Sanderling Resort on North Carolina’s Outer Banks is the place to be. Through February 12, 2020, they’re offering a “Heroes Supporter Helps Ocracoke School” special aimed at rebuilding a school destroyed by Hurricane Dorian. A minimum $5 donation nets you 20 percent off your nightly room rate. When you go, don’t forget your camera. You’ll definitely want to capture your own images of the local wild beach horses. If you love this idea, apply it to your holiday shopping, too: Check out these beautiful gifts that give back.
Cheap winter vacation in the Caribbean
Pack your swim and snorkel gear, because the very chic Oyster Bay Beach Resort in St. Maarten is offering rates starting at $150 per night all winter long. You’ll be treated to their especially Instagram-worthy pool with ocean views, delicious dining, sea breezes, and a quietly trendy international scene. We’re pretty sure this one will be your go-to year after year. Already been to St. Maarten? Pick another one of the best Caribbean islands to beat your winter blues.
Cheap winter vacation in Maui
Dodge the cold American mainland temperatures by escaping to Maui for a romantic stay at the popular Ka’anapali Beach Hotel. This idyllic spot offers surfing, swimming, world-class dining, and a special “Hearts in the Sand” package. Receive three nights of oceanfront accommodations, a bottle of champagne and chocolate-dipped strawberries, a keepsake picnic backpack filled with goodies, dinner for two, and stand-up paddleboard lessons for two through December 22, 2019, for $1,422 plus taxes. Here are some more of the most romantic couples resorts around the world.
Cheap winter vacation in the Bahamas
If you need a quick warm-weather trip, booking a getaway on the Carnival Victory from Miami to the Bahamas is one of the best last-minute travel deals you can find. Not that you really need an excuse for a Bahamian weekend, but the ship offers endless all-you-can-eat buffet options, fun cocktails, swimming, activities, and more. Before you commit to a vacation like this, make sure you know these things travel experts wish you knew about booking a cruise. If you’re worried about getting seasick, make sure you read up on cruise tips to help you prevent it.
Cheap winter vacation in San Francisco
San Francisco’s undeniable flair, art scene, and architectural marvels are enough to draw anyone in—but for those still wondering if they really need to head to northern California this winter, let us present you with some especially compelling facts: The weather is delightful throughout the winter months, the sea life abounds, the seafood is even more plentiful, and you can stay at the normally very expensive Hotel Zoe Fisherman’s Wharf for 25 percent off the best available rates if you book by December 30, 2019. Get ready to get all the Ghirardelli chocolate and see the sights—you won’t regret it. Now that you know about these cheap winter vacations, read on to find out the best budget travel destinations.