The Best Winter Travel Packages

There are two types of winter travelers. Those who head north to enjoy the activities associated with fresh mountain air, such as skiing, snowboarding, snowshoeing, snowmobiling and even dog sledding. Then there are the snowbirds, people who fly south at the first sign of winter in search of sandy beaches and endless sunshine. Regardless of your preference, resorts and hotels often offer specially discounted packages designed to entice guests to their doors.

Here are some of the best winter travel packages:

Whiteface Lodge (Lake Placid, New York)

Whiteface Lodge’s value-packed Ski. Soak. Eat. Repeat offer includes two free lift tickets to Whiteface Mountain and complimentary breakfast each morning to fuel skiers down the slopes. Guests also receive a resort accommodations credit of $50 per night for one-bedroom suites, $75 per night for two-bedroom suites, and $100 per night for three-bedroom suites. To soothe aching muscles, skiers and boarders should consider the resort’s selection of “Alpine Athlete” spa services, taking advantage of a 25% savings on all therapies at The Spa through the package.

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Ka’anapali Beach Hotel (Lahaina, Maui)

Set along the Pacific, Kā’anapali Beach Hotel invites you to spend a few days basking in the warm Maui sun and golden sand with the Sunny Side Up Package which saves you $274. Included are ocean-view room accommodations (for four nights), a buffet breakfast for two on one morning, lunch for two and choice of either snorkel gear or a chaise with an umbrella. The travel dates end on December 22, 2019.

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Curtain Bluff  (Antigua)

Curtain Bluff’s BRR 20% Off Special is the ideal way to escape the winter blues. With all gourmet meals and top-shelf drinks included in the rate, guests can enjoy additional on-property activities such as snorkeling, scuba diving (for certified divers only), sailing, waterskiing, SUP paddle-boarding, sailing, tennis, yoga and more. This inviting Caribbean deal includes 20% off for bookings made for stays between January 3 to 31, 2020 (five-night minimum stay).

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Pebble Beach Resorts (Pebble Beach, California)

For golf lovers, a winter getaway to the legendary Pebble Beach Resorts is sure to top the list. The two-night Winter Stay & Play Package includes two rounds of golf, one on Pebble Beach Golf Links and the other on a choice of Spyglass Hill Golf Course or The Links at Spanish Bay, plus a $100 resort credit. Guests can choose to stay at The Inn at Spanish Bay or The Lodge at Pebble Beach. There’s also an option to book a third and/or fourth night at 20% off. This Pebble Beach offer is valid from November 24 to March 31, 2020.

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Twin Farms (Barnard, Vermont)

An all-inclusive Relais & Châteaux property, Twin Farms serves as the ultimate winter escape, offering the best of seasonal activities amidst the 300 acres of snow, in addition to the unique bespoke programming offered as a part of the Art of a Vermont Winter Series. In hosting this series over the past two years, Twin Farms has brought together the best talent for programming and curated partnerships spanning culinary, culture, adventure, arts, music and entertainment, with guest-chef hosted dinners, intimate cooking classes and furniture workshops in which guests actually make their own table.

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The Resort at Paws Up (Greenough, Montana)

When the blankets of snow start to fall over the mountains of Montana, Paws Up turns into its own private Winter Wonderland. The resort offers countless seasonal adventures, including dog sledding, snowmobiling, snowshoeing, snow tubing and sleigh rides. Rates for Winter Travel Packages start from $523 per person per night and are available January 1 through March 1. Included are all daily meals, nonalcoholic beverages and a selection of beer, wine and well spirits. The package also includes one activity credit of $100 per person.

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The Lodge at Blue Sky (Wanship, Utah)

Why head south when the Wasatch and Uintas Mountain Ranges await? Through a partnership with helicopter outfitter Powderbird, guests of the Lodge at Blue Sky can depart directly from the property on a ten-minute flight to enjoy heli-skiing in the majestic peaks outside of Park City, Utah. The untouched high alpine terrain consists of over 200,000 acres of alpine bowls, steep chutes and glades all blanketed by some of the greatest snow on earth. The accommodations include Sky Lodge, Earth Suites or Creek Houses.

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Steamboat Ski Resort (Steamboat Springs, Colorado)

Best if booked by August 29 (after that you can still receive 25% off—and 10% during holidays—until mid-October), Steamboat’s VIP (SVIP) Program offers 30% off packages with lift tickets, lodging, ski school, rentals, dining and activities. It also offers free activities including night skiing & riding, first tracks, equipment demos, guided snowshoe tours and passes to Steamboat’s famous hot springs. Valid for stays November 23 through April 12, 2020 (there is a 15% discount for holiday period of December 21- January 4, 2020). There are also spa and dining discounts during the same period.

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Marigot Bay Resort & Marina (Saint Lucia)

Take advantage of shoulder-season flight fares to St. Lucia where travelers can find sunny weather and stunning Caribbean scenery without hordes of tourists. Set on the Caribbean’s most scenic harbor, Marigot Bay Resort features locally infused dining experiences and affordable packages such as its 7 Experiences in 7 Days offer, a package that indulges guests in a slew of culturally infused and curated activities such as a cooking demo followed by a body scrub workshop. Book now through September 3, 2020 and get a free seventh night.

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Playa Cativo Lodge (Costa Rica)

Located in the center of Costa Rica’s rainforest and accessible exclusively by boat, Playa Cativo is an upscale beachfront eco-lodge offering stunning accommodations in true harmony with nature. This luxurious hideaway is complete with a new Lotus Spa wellness haven and 18 open-air casitas. Straight from the on-property farm, the lodge offers two multi-sensory dining experiences. The Playa Cativo Essentials Package allows jet-setters to plan the ultimate winter getaway. This four-night package includes local air transfers, a four-night stay, round-trip scenic boat transfers, three à la carte, multi-course meals per day and more.