The Cozy Red Cottage

31 Romantic Winter Weekend Getaways in the U.S.

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The Cozy Red Cottage: December Holiday Calendar
The Cozy Red Cottage: December Holiday Calendar

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Want to whisk your sweetie away on a romantic winter getaway in the United States? It’s time to start planning now. Whether your other half would prefer to curl up in a cozy cabin with a good book or hit the slopes on a ski vacation, frosty fun awaits in big cities, small towns and rural areas across the country. “Aspen has such an undeniable buzz. Alaska is rife for adventure with dogsledding, snowmobiling and even heli-skiing,” says Carolyn Addison, head of product at luxury travel company Black Tomato. “I’m also a big fan of an off-season trip to Newport. It’s so pedigreed and well-heeled but with tremendous character.” Rather catch some rays at the beach? We’ve also included a few scintillating warm-weather locales that snowbirds are sure to love. And, of course, destinations with mild climates and a plethora of outdoor activities (hello, hiking and biking) haven’t been overlooked either. Scroll on and let the sparks fly.

The Cozy Red Cottage:
The Cozy Red Cottage:


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The Cozy Red Cottage:
The Cozy Red Cottage:

Just a three-hour drive from the urban sprawl of San Francisco, Truckee is a picturesque mountain town that’s the perfect home base for exploring the majesty of Lake Tahoe. Fill your days with hiking, snowshoeing, skiing and snowboarding or go for a nostalgic twirl with your partner on the Northstar Village Ice Skating Rink. As the sun starts to go down, the twinkly lights illuminate the western-style main drag that’s full of shops and restaurants for a casual date night.

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The Cozy Red Cottage
The Cozy Red Cottage

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If eye-catching art, Instagrammable sights and tumbleweed-dotted dreaminess are your love language, then we’d highly recommend journeying to Marfa. This hip 1.6-square-mile desert gem in west Texas may be tiny but it’s packed with massively creative energy and cool stuff to see, including the Marfa Mystery Lights and contemporary art installations at Ballroom Marfa and Chianti Foundation. You’ll also want to drop in at Marfa Book Company, which hosts talks, readings and performances. And if you leave without heading to Prada, did you even visit the town? The vast, arid landscape is nothing short of mesmerizing. And because winter isn’t as popular of a time to visit, you might even have the good fortune of capturing some cute couple’s shots sans other tourists.

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New Orleans has a party-centric reputation, and that’s definitely warranted. However, there’s more to the Big Easy than Mardi Gras and Bourbon Street. It’s a rich melting pot of music, cuisine and architecture that’s totally tempting in the winter when the temperature drops yet the offerings remain sizzling hot. If you’ve already done the whole dimly-lit dinner date night thing, why not shake up the after-dark escapades with a haunted bar crawl? (If nothing else, it’s a great excuse to hold your sweetie extra close.)

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Those who self-identify as snowbirds (and really any couple keen to escape the cold) should fly down to Key West for a sun-splashed, stress-free weekend of enviable weather, daiquiris, beach strolls, candy-colored sunsets and bar hopping in Florida’s southernmost point. Don’t stay out too late because you’ll need to rise early for a snorkeling excursion to North America’s only living coral barrier reef. The Hemingway House is also a must, as well as a stroll down the historic seaport and a trip to the Key West Garden Club.

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A *literal* oasis in the middle of the Sonoran Desert and the retreat of choice for A-listers dating back to the Golden Age of Hollywood, Palm Springs still tops the list of weekend getaways for romance and relaxation. With championship golf courses, gorgeous mountain views, stylish hotels, hot springs and some of the most swoon-worthy examples of mid-century modern architecture in the country, it’s easy to see why everyone who visits Palm Springs falls in love with this sun-splashed idyl. Start your day with a ride in the aerial tram to the top of San Jacinto Peak (have lunch at the top), then spend the rest of the day in the air conditioning. The Palm Springs Art and Air Museums offer plenty to see. For a cool slice of architectural history, head to the visitor’s center, a space-age creation and former gas station. Should you have a hankering to explore the outdoors, winter is the time to do it, and Joshua Tree isn’t far away.

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If you live anywhere in the Midwest, chances are you’re only a direct flight (or, maybe, even a reasonable drive) away from Chicago. While the weather in the Windy City might be a bit unforgiving in the winter months, the abundance of incredible things to do indoors—from visiting world-class museums and soaking in skyline views to cozying up in cocktails bars and splitting a deep-dish pizza with your person—along with seasonal attractions such as Christmas markets make it an enticing urban escape.

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Winter in Scottsdale is just wow. It won’t be scorching like the summertime (that’s actually a good thing because if you’ve ever visited in July that’s a one-and-done situation), but you will get to enjoy clear, sunny skies. The picture-perfect vacation weather feels particularly well suited for partaking in the myriad outdoor activities, ranging from hiking in the Sonoran Desert to golf. Don’t forget to add spa sessions (couples massage, anyone?) and trips to the nearby Desert Botanical Garden to your weekend itinerary. You can’t leave town without hitting the Cosanti Foundation or the Scottsdale Rodeo Museum, either.

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Heaps of powder turn Aspen into one of the most magical places on the planet. Killer skiing and snowboarding are a given. But that’s only part of the appeal. Thanks to high-end shops, intimate restaurants for candlelight dinners, luxury resorts and cultural attractions such as the Aspen Art Museum, you can still have an incredibly romantic weekend without ever even putting on snow boots. You won’t regret splurging on a romantic room with luxury cowboy-inspired decor at Hotel Jerome, which gives you a taste of life in the 1800s (with modern comforts, of course). Be sure to also catch a performance at the Wheeler Opera House, designed by the same architect who did the hotel.

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The Green Mountain State has so many dreamy winter destinations it’s almost impossible to pick just one. But we’ve got to give it up to Woodstock for being the perfect New England escape and the quintessential destination for a quiet weekend away without the kids. This small town attracts couples with its rolling hills, classic New England architecture and ample outdoor activities. Be sure to put the Marsh-Billings-Rockefeller National Historic Park on your must-see list, plus all the covered bridges. Not to mention the delightful boutique shops, delicious farm-fresh dining as well as storied inns that blend heritage and homespun comforts.

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While the masses may flock to Newport in the summer, this heritage-rich coastal enclave is pretty much guaranteed to reignite passion in the slower, frostier months. A blanket of glittering white snow covers the opulent Gilded Age mansions. There are tons of festive events and storefronts twinkle with lights. A chill in the air invites extra cuddles and sipping mulled cider overlooking the harbor. It’s also way easier to score coveted reservations at beloved restaurants like Clarke Cooke House and Giusto.

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The city so nice they named it twice! Whereas many places slow down in the winter, the Big Apple continues to buzz in December, January and February. Whether you’re skating on The Rink at Rockefeller Center, ambling through the quaint streets of the West Village, snow-shoeing in Central Park, navigating the many masterpiece-filled rooms at The Metropolitan Museum of Art, catching a Broadway show or savoring a candlelit dinner at a Michelin-starred restaurant, New York comes up big in the romance department.

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Kauai (aka the “Garden Isle”) will steal your heart with its unspoiled beauty—pristine bays, secluded coves, lush rainforests and dramatic cliffs. A helicopter tour over the Na Pali Coast and Waimea Canyon is a must-do activity when in Hawaii and an experience that’s guaranteed to create bonding memories to last a lifetime. For active duos, there’s also mountain biking, volcano voyages, ATV tours and snorkeling. Of course, the fact that it’s bikini weather in the winter certainly doesn’t hurt either.

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When the forecast calls for snow, it’s time to hightail it out of the city to a quaint town. The Midwest is great—albeit freezing—during the frosty season. We’re especially sweet on Galena, a former lead-mining town with all the makings of a very adult and amour-inducing weekend that’s only three hours from Chicago. It has preserved 19th-century buildings (like the Ulysses S. Grant Home), antique shops on the historic main street, peaceful nature trails and farm-to-table eateries.

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The state of Oregon is blessed with tons of beautiful places and charming small towns. Situated near the second-largest wilderness area in the state, Sisters offers couples access to majestic peaks (ever heard of the Three Sisters?), alpine meadows, waterfalls, lava fields, glaciers, freshwater streams, sparkling lakes, forests and all sorts of outdoor adventure. In the winter, that means snowy hikes and skiing. Woodsy cabins with oversized soaking tubs, king beds and fireplaces bring the romance at FivePine Lodge & Spa.

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Top-notch skiing makes a compelling case for jetting off to Bozeman during the snowy season. But that’s not all! Winter also brings romantic sleigh rides and adrenaline-raising ice climbing. Lovebirds can unwind with a dip in the natural hot springs, sample stouts at local breweries and shop the artisan boutiques along Main Street. For a unique date night, head to the planetarium to stare up at the majesty of the cosmos at Montana State University’s Museum of the Rockies.

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Jackson Hole entices any time of year. Although, we’ll admit that Yellowstone and Grand Teton National Park are both somehow even more breathtaking blanketed in snow. Love skiing and snowboarding? The area boasts three winter resorts: Jackson Hole Mountain Resort, Snow King Mountain Resort and Grand Targhee Resort. Downtown has adorable shops, Western-inspired bars and wonderful restaurants. Be sure to snap a photo with your darling in front of the famous antler arches to keep as a memento.

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Dreaming of stealing away to one of the prettiest small towns in New England for the weekend? The moment you gaze upon Penobscot Bay, the glistening harbor and the well-preserved 19th-century homes covered in fresh flakes, it’ll become abundantly clear why Camden is so special. It’s obviously worth shouting out the seafood eateries, local wineries (apparently, Maine produces some pretty good vino?) and performances at Camden Opera House. We’d be remiss not to mention the cozy inns with hot tubs and fireplaces.

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Wine, food and romance go together like, well, wine, food and romance. During shoulder season in Sonoma, the climate remains mild, yet hotel rates drop. And what’s sexier than having extra money in your pocket to spend on fresh-from-the-field farm and biodynamic vino from a local producer? The Reserve Experience at Hamel Family Wines marries a four-course meal with limited-production Cabernet Sauvignon and other terroir-driven sips. When you’re ready to take advantage of the good California weather, head outside to Sonoma State Historic Park or the Overlook trail. If less walking is more your speed, you can still count the Sonoma Valley Wine Trolley as an outdoor activity.

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At first, Sandpoint may not seem like the most obvious pick for a red-hot winter getaway. But its sparkling Lake Pend Oreille, awe-inspiring mountains and 300 inches of snow say otherwise. While you’re there, take advantage of the array of outdoor activities (who’s up for cross-country skiing, ice fishing and snowmobiling?), grab a pint at MickDuff’s Brewing Company and see a concert at The Panida Theater. Picture you and your loved one snuggling under a blanket on the porch of this peaceful log cabin.

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Want to escape the cold? Venture to Miami Beach for sunshine, great food, nightlife, Art Deco architecture and seaside canoodling with your partner. The average temp in January is 76 degrees, which means you can spend days basking in the golden rays. Snag tickets to the Vizcaya Museum and Gardens and spend a morning wandering the beautiful villa on Biscayne Bay. Then, pop by Bayside Marketplace, a two-story shopping extravaganza, before heading to Pérez Art Museum. What’s on tap for evenings? Dinner at a trendy restaurant, followed by sipping cocktails at a swanky lounge, going dancing or hitting a club. We’d suggest staying at The Savoy Hotel & Beach Club for the sexy, grown-up vibe.

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New England nostalgia is very much on display in Cornwall—and a dusting of snowflakes only makes this tiny town in Litchfield County even prettier. The slopes of Mohawk Mountain lure skiers and snowboarders of all skill levels from all over the East Coast. Rugged and remote, Wyantenock State Forest encompasses 4,000 acres. On a given afternoon in the winter, you probably won’t see another person (besides your partner, of course). The West Cornwall Covered Bridge is also must-see.

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Why visit Loretto? Beautiful views, country cooking and bourbon! Kick off your trip with a scenic drive along the Bluegrass Parkway. Take a tour of Maker’s Mark Distillery to learn how the famous spirit is made (the heavenly aromas are definitely an aphrodisiac), explore the limestone cellars and slog back a few tipples. The other can’t-miss attraction? The My Old Kentucky Dinner Train. There are several ride options, including teatime, bourbon, lunch, dinner, the North Pole Express and even a murder mystery excursion.

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A fairytale destination in every sense that’s only two hours from Seattle, Leavenworth is one of the best mountain towns in the United States and a frontrunner for romance. This Bavarian-style village in the Cascade Mountains brims with fresh alpine air, storybook architecture, beer halls (like Icicle Brewing Company) and all the schnitzel you can eat. Don’t miss the biggest pretzel of your life at Leavenworth Cider House and an alpenhorn performance at Enzian Inn. The charm level only rises when the flakes fall. Plus, there are awesome ski slopes. It really does tick all the boxes of an ideal winter vacation spot for couples.

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You could easily make the case for Charleston being the most romantic city in the South. The weather in the winter is generally mild, so that’s quite appealing (especially for folks in the frosty Midwest and Northeast). Don a light jacket for strolls along The Battery and the Joe Riley Waterfront, savor Low Country cuisine at the myriad award-winning restaurants and take couple-y pics in front of Rainbow Row.

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Located just two hours from the Big Apple, Hudson has established itself as one of the most enchanting (and convenient) places for urbanites to escape city life for a few days. If indie shops, heritage-rich architecture and farm-to-table restaurants sound right up your alley, might we suggest stealing away to this charming country town for a winter weekend? The colder months also bring ample opportunities for fun outdoorsy activities like cross-country skiing and cozying up at the quaint hotels around town.

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Consistently ranked among the best mountain destinations in North America, Park City is a year-round playground for outdoor recreation. But this tourism darling shines even brighter in the winter with easy access to Park City Mountain and Deer Valley Resort. It’s no secret that the slopes are epic. Sundance Film Festival is another big seasonal draw card. You’ll also find fantastic food, many boutiques along Main Street and upscale hotels. For some high-altitude excitement your honey won’t soon forget, book a hot-air balloon ride.

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An inimitable combination of charm and grace makes Savannah utterly irresistible. When the thermometer dips, so do the crowds. That makes it even more pleasant to meander hand in hand along the cobblestone streets, have a little picnic in Forsyth Park (with provisions from Back in the Day Bakery), gawk at the antebellum architecture, do a spooky ghost tour and revel in the pleasure of a riverboat cruise. The hearty Southern fare and boozy drinks are surefire ways to warm up in between exploring.

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Couples venturing to Lanesboro can expect arts, culture and a leisurely pace that seems tailor-made for reconnecting. The chilly weather in December, January and February encourages cozying up (body warmth is a real thing). There are vibrant galleries, studios and performances by roving thespians. The Commonweal Theatre Company stages a lineup of comedies, dramas and musicals. Hunker down at a rustic log cabin that’s located on the Root River Trail and only a few miles from downtown.

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It’s no secret that Vail is in one of the most charming towns in Colorado. For pairs who enjoy skiing and snowboarding, few places compare to this storied resort destination. Envision yourself sharing gondolas to the top of the summit while the flakes gracefully fall, racing side by side to the base of the mountain and indulging in some après-ski revelry. The perfect spot to settle in after hitting the slopes? Austria Haus Hotel, a romantic retreat with Swiss-chalet aesthetics in the middle of Vail Village. But before you settle in for the evening, grab a pint at Vail Brewing Company.

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Admittedly, Fairbanks isn’t a feasible weekend getaway for most folks. That doesn’t mean it’s off the table for all couples. As if the chance to witness the northern lights wasn’t seductive enough, the mix of active and leisure pursuits really seals the deal. Try dog mushing, heat things up at the thermal springs or plan a trip to the Arctic Circle. We also love the idea of reserving a log cabin and glimpsing the aurora borealis from the comfort of your own deck.

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Albuquerque may not be the first destination that comes to mind when it comes to romantic getaways, but trust us, this beautiful spot ticks all the boxes. It’s the perfect mixture of rural and metropolitan vibes—without the dreary isolation or overcrowding. Head over to Old Town for a day of limitless shopping and learning all about New Mexican culture, before ending the night with a delicious dinner for two courtesy of Farm and Table, a sophisticated, cozy restaurant serving fresh and locally grown food.

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