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The 13 Best Romantic Winter Getaways for a Couple’s Trip

For some, romantic winter getaways evoke images of curling up by roaring fireplaces with glasses of bold red wines and watching the snow come down through picture windows. Others prefer escaping to sunshine-filled beach locales, where the biggest decisions to make are whether to order margaritas or a bottle of champagne to the cabana. The truth is, it all works, because the only requirement of a fabulous couple’s trip is being together in a wonderful place—and letting the hotel staff spoil you.

Here, we’ve rounded up some of our favorite hotels and resorts that create unforgettable experiences for two—from a New England classic to Hawaii, Mexico, the Maldives and more.

Our team can help you responsibly navigate Covid travel policies, current restrictions, testing and protocols—to plan a special trip, whenever you’re ready. Contact Indagare for assistance in booking the best romantic winter getaways for you and your significant other.

Beaches for Two

Little Palm Island, Florida

This bungalow-only haven for adults sits on its own private island, with outdoor copper tubs and private firepits at each of its thatch-roofed cottages.

The Romance Factor: No TVs in the room means no distractions from the four acres of beachfront—or your significant other.

Related: Dispatch from South Florida: The Latest from Miami & Palm Beach

Four Seasons Lanai, Hawaii

Zen-ed out interiors and lush gardens overlook Hulopoe Bay, one of Hawaii’s dreamiest coves (on one of its dreamiest islands).

The Romance Factor: A private, five-course dinner under the stars with customized wine pairings.

Las Ventanas al Paraíso, A Rosewood Resort, Los Cabos, Mexico

A honeymoon favorite, the resort’s open-air villas fronting a wide beach come with private pools. At sunset, hundreds of candles and trees strung with twinkling lights add an ethereal glow.

The Romance Factor: A dedicated Romance Team, on hand to craft custom experiences and special moments for couples.

“The resort and its understated elegance, unparalleled service and luxe, organic feel coupled with the attention to every single detail surpassed every expectation I could imagine. ​The staff was incredibly personable and we felt welcome from the moment we arrived. I really enjoyed the couple’s massage and private beach cabana. Our room was so gorgeous. This was my most favorite vacation ever. We look forward to returning very soon.”  —An Indagare member

Related: Where to Stay in Los Cabos: The Best Resorts for Every Traveler

Romance on the Range (and the Slope)

Dunton Hot Springs, Colorado

In this former Rocky Mountain ghost town, historic log cabins have been restored and retrofitted into stylish woodsy hideouts.

The Romance Factor: The Well House cabin, with its wood burning stove and private hot spring and cold plunge.

“When we finally arrived at the front gates of Dunton Hot Springs, I had seen no more than four cars and 20 cabins during the last 40 minutes of the drive. I truly felt as if I had been transported back to the 1830s and the original mining town of Dunton—just as owner Cristoph Henkel intended.” —Indagare’s Lizzie McGirr

The Ranch at Rock Creek, Montana

A stylish interpretation of the Wild West, the Ranch has 6,600 acres of land, with miles of snowshoeing, cross-country skiing and horseback riding trails in Big Sky Country.

The Romance Factor: Sleigh rides over the snowy terrain in a traditional buggy, followed by hot cocoa (or toddies).

“It was all pretty perfect. The service was great, the food was fabulous and it’s so very beautiful.” —Indagare member Marianna Green

The Little Nell, Aspen, Colorado

The ski-in/ski-out property at the base of Ajax Mountain is Aspen’s most coveted address.

The Romance Factor: A bottle of champagne in the elegant Element 47 restaurant and lounge, or in your contemporary room with a fireplace and mountain views.

Related: Aspen Winter News: What it’s Like This Season 

Washington School House Hotel, Park City, Utah

A 19th-century limestone school in Park City has been reborn as a hip, 12-room boutique hotel with a ski lounge, pool and guests-only bar.

The Romance Factor: Private dining from the hotel’s excellent chef, creating a customized dinner date just for you.

“The Washington School House was delightful. The penthouse room was one of the prettiest and most comfortable rooms that we have ever stayed in. The included food and wine was delightfully delicious.” —Indagare member Shelby Butterfield

Cozy Quick Getaways

Blackberry Mountain, Tennessee

The smaller, more rustic sister to Blackberry Farm, spread over eight square miles, showcases Appalachia chic vibes with a wellness bent.

The Romance Factor: The one-bedroom Clingmans Cottages, with a spa room for in-unit massages, plus an outdoor soaking tub and fireplace.

“While at Blackberry Mountain in December, it was easy to fall in love with the snow-crisped mountain air and hikes to the Catspaw Ridge to eye-widening views of the dappled, blue-hued Great Smoky Mountains. With rosy cheeks, a final ascent to the top of Goat Hill at sunset filled us with that sense of wonder we’ve been missing these last months—and after a super-sensory dinner at the Three Sisters restaurant, we were content to sit by the fire, ordering whiskey from the bar and savoring all we had experienced.” —Indagare’s Elizabeth Harvey

Related: Our Favorite U.S. Hotels with Private Cottages or Villas

Twin Farms, Vermont

This bucolic 300-acre estate promises excellent food, plus fabulous décor and priceless art—Jasper Johns, Frank Stella, Roy Lichtenstein—in its 10 themed villas (kids 14 and up only).

The Romance Factor: Meadow Cottage, whose traditional clapboard exterior conceals a Moroccan tent interior, with a mosaic fireplace, rich textiles and two-person pedestal tub.

“With its vaulted, beamed ceilings, walls of well-thumbed books, fascinating artwork and handpicked antiques, Twin Farms was clearly once a beloved private home—the former estate, as it happens, of Nobel Prize–winning author Sinclair Lewis and his wife, journalist Dorothy Thompson, who lived there in the 1920s.” —Indagare’s Eliza Scott Harris

Related: The Most Romantic Hotels in the U.S.

Urban Retreats

Commodore Perry Estate, Austin, Texas

This former private home—an ornate Spanish Colonial and Italian Renaissance Revival mansion—opened in Summer 2020 as Austin’s newest escape, set on 10 manicured acres.

The Romance Factor: The floral overload that is the LaVerne Suite, with its draped canopy king bed under vaulted ceilings.

Related: Wall Street Journal Special Offer to Commodore Perry Estate

Zero George, Charleston, South Carolina

Charleston’s most picturesque hotel, Zero George has 18 airy rooms set in five 150-year-old townhomes.

The Romance Factor: A sunset sail on a private yacht around the harbor, admiring the steepled skyline.

Far-Flung Flings

Cheval Blanch Randheli, Maldives

Glass doors and cathedral ceilings maximize the views at this ultra-modern, 45-villa resort on its own island in the Noonu Atoll, where couples can spend the day on the water, in the spa or at the beach.

The Romance Factor: The spa’s breezy Orchidée Villas, overwater bungalows for couple’s treatments from Guerlain.

Le Royal Mansour, Marrakech

King Mohammed VI’s personal passion project, this hotel with its 53 palatial riads—built around a gorgeous pool and Moorish-style gardens— serves as an opulent enclave for privacy and pampering.

The Romance Factor: The three-story Premier Riads have 1,800-square-feet of glamorous areas to relax, from the ground-floor private courtyards to the rooftop plunge pools and tented lounges.

“We have stayed at many fine hotels, Ritz Paris, Aman Tokyo, Baur Au Lac Zurich, and none compare to the level of seamless service and indulgence of this exceptional hotel. I will argue that nowhere offers such an extravagant experience. If you wish to experience what it may be like to live like royalty, this is probably as close as you can get in a hotel experience. Oh, and the food and beverage is as exceptional as the hotel.” —Indagare member Brian Thomson

Related: The Most Romantic Hotels in the World

Our team can help you responsibly navigate Covid travel policies, current restrictions, testing and protocols—to plan a special trip, whenever you’re ready. Contact Indagare for assistance in booking the best romantic winter getaways for you and your significant other.

– Peter Schlesinger on February 10, 2021

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