Find the Best Price
Show Prices Change Dates

Best Winter Vacations

Winter never seems too bad at first. But after awhile, when the cold prevents your car from starting and the snow turns to gray, this season starts to get the better of us. Don't worry: We've come up with a list of vacation destinations to help you defeat your seasonal doldrums and cure the wintertime blues.  

Expand Map Expand Map
Belongs on list?
506 200

Why go: Winter ushers in tourists and inflated room rates, but the cost is oh-so worth it. Relax on the golden sands of Po'ipu Beach or enjoy the scenery along Lumahai. And though the hike along the northwest Na Pali Coast is strenuous, the landscape is glorious. Read More»

Read On: Top Things to Do in Kauai

Belongs on list?
364 191

Why go: You'll get two cultures for the expense of one island vacation. Visit French St. Martin for some duty-free shopping and fine dining. Afterward, hop over to Dutch St. Maarten for the lively clubs and casinos. Or forget about picking sides and focus on the island's white-sand beaches. Read More»

Read On: Top Things to Do in St. Martin - St. Maarten

Belongs on list?
358 225

Why go: In Playa del Carmen, the beach atmosphere is laid-back, the mixed drinks are strong and the golf courses are plentiful. But ensure the price is right before you book — the warm temperatures attract snowbirds, and the hotel rates can fluctuate dramatically. Read More»

Read On: Top Things to Do in Playa del Carmen

Belongs on list?
435 245

Why go: In Puerto Rico, you can enjoy the perks of the Caribbean without leaving the country. Attractions range from adventurous (exploring the underground caves of Rio Camuy Cave Park) to historic (traversing the 500-year-old El Morro walls) to luxurious (relaxing on a Vieques beach). Read More»

Read On: Top Things to Do in Puerto Rico

Belongs on list?
361 244

Why go: Key West makes an ideal winter getaway for those looking for warm weather, frozen daiquiris and mellow afternoons. Snorkeling and scuba diving are big here, and you can hit one of the bike trails to shake off the cobwebs from your winter hibernation. Read More»

Read On: Top Things to Do in Key West

Belongs on list?
152 72

Why Go: On the other side of the equator, summer is in full swing. Scenic Queenstown is chock-full of shops and cafes. And as an adventure-seeker's paradise, Queenstown teems with intense adrenaline-pumping activities that are sure to get your heart racing. Read More»

Read On: Top Things to Do in Queenstown

Belongs on list?
286 322

Why go: With warm temperatures, a riotious night scene and plenty of funky boutique hotels, Miami Beach offers plenty of entertainment options. Do some shopping at Lincoln Road Mall and spend the rest of the day soaking up the sun on South Beach. Read More»

Read On: Top Things to Do in Miami Beach

Belongs on list?
274 151

Why go:  For such a tiny pocket of the Yucatán, Tulum offers plenty of things to do. Visit the Mayan Ruins, of course, but also consider snorkeling through the cenotes area or scheduling a massage at one of the many beachside spas. Just bring a thick pocketbook. Read More»

Read On: Top Things to Do in Tulum

Belongs on list?
289 67

Why go: December ushers in Costa Rica's dry season, leaving only 70-degree temperatures to accompany you on your hike through the rainforest. And if you visit in January, you'll find the tiny country basking in the pura vida while reveling in fiesta time. Read More»

Read On: Top Things to Do in Costa Rica

Belongs on list?
192 66

Why go: Lake Tahoe is beautiful no matter the season, but you'll want to bring a camera to capture the area's sparkling snowy scenery. When you're not admiring the powder, tackle it at one of the four massive ski resorts. Read More»

Read On: Top Things to Do in Lake Tahoe

Belongs on list?
96 88

Why Go: In the winter, skiers from across the globe make the trek to Olympia SkiWorld — a network of eight ski resorts located around Innsbruck. When you're not on the slopes, do your holiday shopping at the local Christmas market along Maria-Theresien-Strasse. Read More»

Read On: Top Things to Do in Innsbruck

Belongs on list?
107 76

Why go: This fun and funky Colorado town draws thousands of visitors each year with its vast array of sweet slopes. Spend your days shredding powder and your nights warming up with a drink in one of the local hangouts. But be sure to make your travel plans several months in advance for the best rates. Read More»

Read On: Top Things to Do in Telluride

Belongs on list?
114 104

Why Go: Vail boasts enchanting views from nearly every angle. Try a few runs at the Vail Ski Resort; then steal away to the luxurious spas and restaurants. But you'll need to reserve your hotel room at least two months in advance or Vail's celebrity clientele could nab the best rooms before you. Read More»

Read On: Top Things to Do in Vail

Belongs on list?
159 218

Why go: Though it may be too cold to take a dip in the Mediterranean, you'll still find the city's beaches to be a popular gathering spot. And come nightfall, you'll find Tel Aviv alive with entertainment, from low-key bars to eardrum-busting clubs. Read More»

Read On: Top Things to Do in Tel Aviv

Belongs on list?
249 249

Why go: Nestled at the foothills of the Canadian Rockies, this tiny town really knows how to enjoy the colder months. With three resorts to choose from, skiing is the main attraction here, while the surrounding Banff National Park offers plenty of winter hiking opportunities. Read More»

Read On: Top Things to Do in Banff

Also Consider for Best Winter Vacations...

Belongs on list?
402 538
Belongs on list?
256 34
Belongs on list?
168 53
Belongs on list?
149 64

in Best Winter Vacations

Check Flights

See best fares from Orbitz, Expedia, Kayak & more!
Round Trip One-Way Non-stop Only
Please enter missing information