The 11 Best Off-Season Winter Travel Spots to Make Your Travel $$$ Go Farther

• Best For: families, friend groups, sweater obsessives
• Where to Stay: Brewster Pond Home (from $240/night, sleeps 8) Beach Glass Cottage (from $301/night; sleeps 7); Fireplace Carriage House (from $314/night; sleeps two)

Winter in Cape Cod can be chilly and gray, but there’s still plenty to see and do, including beach walks, Christmas celebrations and museums that are blissfully free of crowds. Popular destinations include Provincetown, Wellfleet, Nantucket and Orleans, although you can find cozy, charming B&Bs and inns scattered all over the Cape. (For example, Gabriel’s Provincetown Inn features winter-ready fireplaces and soaking tubs.) Explore the John F. Kennedy Museum or the Sandwich Glass Museum, or bundle up for a stroll along the Cape Cod Rail Trail. The seafood obsession also doesn’t stop just because it’s winter—look for beloved spots like The Beachcomber, Skipper Chowder House and Lobster Pot to indulge in lobster rolls, local oysters and clam chowder.

• Best For: families, couples, relaxation junkies
• Where to Stay: Cave Home (from $534/night; sleeps 6); Scorpios Beach Hotel (inquire for rates); Caldera Premium Villas (from $394/night)

Peak tourist season in Santorini runs through September, but the late fall and winter are a perfect time to enjoy the rugged Greek island without crowds blocking your every move. Airlines typically offer lower flights during that time period and the resorts became much more affordable thanks to cooler weather and shorter days. While you may not want to sunbathe, Santorini’s cliffside towns, Fira and Oia, remain lively, with cafés and restaurants open all year (watching the sunset in Oia is the island most popular attraction). Visitors can also hike, tour wineries like Santos Wines or take a boat tour around the famed Caldera. Book a room at the tranquil, tucked away Scorpios Beach Hotel or rent one of the Caldera Premium Villas, which offer views of the water. To take full advantage of Greece off-season, add Mykonos to your itinerary, or opt for a few days in Athens before or after.

• Best For: solo travelers, families, nerds
• Where to Stay: Agora Tokyo Ginza (from $195/night); All Day Place Shibuya (from $247/night); Hotel Sunroute Plaza Shinjuku (from $211/night); Conrad Tokyo (from $782/night)

Tokyo is a bucket-list destination for many travelers, but the spring and summer months can be overly crowded and, frankly, overwhelming in the Japanese capital. Although the weather can be chilly, late fall and winter are a great time to visit instead, especially when you can seek out hotel and flight deals during off-peak times. Stay right in busy retail area Shibuya at the All Day Place Shibuya, or splash out at the Conrad Tokyo, which caters to families. There’s a lot to experience in Tokyo, but some of the highlights include Tokyo National Museum, Tsukiji Fish Market, teamLab Planets, Mori Art Museum, and Golden Gai, a collection of lively alleyway bars. Delicious food is also plentiful, from ramen to tempura to sushi, and you really can’t go wrong (but do queue for Nemuro Hanamaru Ginza, one of the most sought-after sushi conveyer belt restaurants in town).  

• Best For: adventurers, couples, nature lovers
• Where to Stay: Hotelito Azul (from $168/night); Jungle Villa (from $260/night; sleeps 2); Apartment with private pool (from $160; $125/night; sleeps 2); La Zebra (from $337/night)

Tulum maintains a steady temperature of 80 degrees F during the winter, making it an ideal off-season getaway for those seeking some sun. The prices tend to increase from December, so plan a trip in early winter when hotels lower their prices and offer deals for longer stays. Skip the bigger resorts and book into a boutique property like La Zebra, a beachside spot with an expansive spa. While you can certainly spend your trip relaxing by the pool, Tulum itself boasts impressive Mayan ruins and a charming downtown. Nearby, go for a swim in the Gran Cenote, visit beloved beach Playa Paraíso or take a drive to snorkel in Akumal. The food in Tulum is top-notch these days—seek out Moro, Hartwood and NÜ Tulum. 

• Best For: couples, solo travelers, culture buffs
• Where to Stay: CitizenM Geneva (from $210/night); Hotel Rotary Geneva – MGallery (from $292/night); The New Midi (from $239/night); Mandarin Oriental Geneva (from $663/night)

While many people jet to Switzerland in the wintertime to take advantage of Alpine skiing, the country’s cities tend to be far less crowded, with lots to see and do. Geneva, known as the home of the United Nations, is a great pick off-season since most travelers simply use it as a stopover on the way to Chamonix. Because of its proximity to France and its international vibe, the city boasts cuisine from around the world, including vibrant Peruvian spot Yakumanka and La Buvette Bains des Pâquis, located on a swimming pier. Visitors can explore museums like the Museum of Modern and Contemporary Art and Musée d'Art et d'Histoire, or take a guided walking tour of Geneva’s old town. Enjoy scenic views of the Rhône river from the rooms at the Mandarin Oriental Geneva, a recently-revamped property that frequently has packages on offer. Nearby, Lausanne is home to the Olympic Museum and a popular Christmas market that runs from the end of November.

• Best For: solo travelers, groups of friends, nature lovers
• Where to Stay: Exeter Hotel (from $255/night); Home in Reykjavik (from $138/night; sleeps 3); Iceland Parliament Hotel (from $432/night); Reykjavik Edition (from $638/night)

Iceland has become one of the top international destinations for travelers over the past five years, thanks in part to its incredible landscape and plethora of outdoor activities. Although daylight is in short supply in the winter, the off-season can be a great time to experience Reykjavik, Iceland’s main city. Not only do you have a good chance of spotting the northern lights, but there are natural hot springs throughout the island country, including the famed Blue Lagoon. Grab a room at the harborside The Reykjavik Edition or opt for the centrally-located Iceland Parliament Hotel. Nearby, the Pósthús Food Hall & Bar is great for a low-key lunch before exploring Rainbow Street and The National Gallery of Iceland. If you want to get outdoors in the snow, take a day trip to Thingvellir National Park or Hraunfossar.

• Best For: couples, families, foodies
• Where to Stay: Golden Tower Hotel & Spa (from $727/night); Iris Cottage Villa (from $115/night; sleeps 6); Renovated Apartment in Medieval Village (from $102/night; sleeps 6)

Your dream of renting a Tuscan villa is even more achievable off-season, with lower prices and the cozy vibe of winter. The region of Tuscany, which includes Florence, Pisa, Siena, and Livorno, is just as compelling during the cooler months as it is in the summer—and with far less tourists at iconic attractions like the Uffizi Galleries and the Leaning Tower of Pisa. A trip to the area can be tailored to the preferences of any traveler, whether you prefer to explore a city like Florence or to unwind in the countryside. Splurge on a stay in real-life castle Castello di Vicarello, a luxury hotel that welcomes guests in all seasons, or make the actual villa from Under the Tuscan Sun your holiday home. While some of the local wineries shut down for the winter, there is plenty to eat and drink at every turn and you can even try your hand at truffle hunting.

• Best for: sun worshippers, families
• Where to Stay: Stay Hotel Waikiki ($118/night); Waikiki high-floor condo ($145/night); Shoreline Hotel Waikiki ($200/night); Kuhio Banyan Club ($149/night)

After the crush of summer crowds have gone home and before the end-of-December Christmas and New Year’s vacay crowds arrive, there’s a blissful whoosh of visitors leaving Hawaii, giving you pleasantly uncrowded trails, beaches and restaurants. (That goes for January, too…a lull leading up to the big rush of spring break.) All the islands are dreamy and easily accessed, but you can enjoy a nice blend of high-low Hawaii if you stay in Honolulu and take a sightseeing cruise to see the koholā (humpback whales) migrate in warm Hawaiian waters to breed and calve their baby whales, hike Manoa Falls and browse for resort wear at the Royal Hawaiian Center (and be sure to save room for Island Vintage Shave Ice).

• Best for: art buffs, nature lovers
• Where to Stay: Chic minimalist apartment ($120); El Cosmico ($146/night); Thunderbird Hotel ($201/night); Hotel Saint George ($295/night)

This West Texas arts mecca cools down to a set of sunny days in the ‘70s come October-November, when the throng of summertime arts festivalgoers thin out, making way for fans of funky music, casual good food and stunning sunsets. It is a popular destination for stargazers and photography enthusiasts due to its dark sky reserve status, thanks to minimal light pollution and a clear atmosphere that makes the Milky Way and other celestial phenomena just pop. You can see the permanent art sites like the Prada installation and works by Donald Judd, the artist whose 1970s settlement in this area put it on the arts map. And don’t miss the Marfa Mystery Lights on the horizon southeast of town.

• Best for: holiday lovers, history buffs, architecture lovers
• Where to Stay: Yours Truly Hotel ($103/night); Kreis Residenz Munchen ($109/night); Motel One München-Parkstadt Schwabing ($131/night); Leonardo Royal Hotel Munich ($108/night)

This Bavarian city is a shoulder-season bargain, with one important caveat: Avoid Oktoberfest, the festival of beer and bratwurst, held the last week in September and first week in October. Prices are quadrupled, crowds are teeming and no one wants to remember their holiday from the smell of stale spilled beer. Instead, head mid-October through January, for a bracing cold-weather tour of the very old—Baroque architecture—and the extremely new—luxury fashion in the Maximilianstrasse. Hike the foothills of the Alps and see the fairytale spires of the Neuschwanstein Castle on a day trip, and if you visit late November and December  experience the Munich Christkindlmarkt in Marienplatz square, a Christmas market that dates back to the 14^th century.

• Best for: opera lovers, romantic long weekends
• Where to Stay: Camden Riverhouse Hotel ($136/night); The Country Inn at Camden Rockport ($141/night); Camden Harbour Inn ($235/night); Camden Hills Studio ($288/night/sleeps two)

There’s a reason this small town on Penobscot Bay has been used for movie sets since the early 60s’ Peyton Place—it's picture-perfect Americana. The gorgeous high street has historic buildings, set off from a crescent bay where sailboats bob peacefully. In fall, the surrounding area displays a perfect copper/rust/amber medley making this leaf-peeping paradise. So many great seafood restaurants (and don’t you date ask for Manhattan clam chowder!), local wineries turning out esteemed bottles and the glorious Camden Opera House. For the most romantic stay, book a room with a fireplace, or at least have a nightcap curled up in front of one.