Celebrating Christmas or ringing in basically any year but the one we just had at a five-star hotel is a once-in-a-lifetime experience, the stuff of which our childhood fantasies are made. And while things are different in 2020 — you’re probably not going to grandma’s, and you’re certainly not going to Europe — there’s still a festive winter guesthouse in reasonable driving distance of just about any point in America.
The list below features an entirely different assortment of hotels than we normally would curate for this occasion. Think less caroling, more remote backcountry cabins at 11,000 feet — or private chalets perched on the outcropping of a glacier in Alaska. Seriously: This is a magical, magnificent collection of experiences.
We need to add: the decision to travel this year is deeply personal, and political, and moral. We’re publishing this guide to the best holiday hotels with an eye to better times, and years, to come. If you’re leisure-traveling — and your correspondent, among many others in the travel industry, is not — remember that expectations and behaviors now vary tremendously from state to state, brand to brand and enclave to enclave, and they’re changing by the day. All of these hotels are adapting in ways large and small to the realities of pandemic-era travel, and it is incumbent upon us, as travelers, to ensure that we patronize businesses whose values align with our own. If it’s important to you (and for our money, it should be) that guests are masked in common areas, be sure the hotel requires it.
It should go without saying that any travel should begin and end with minimal, as-safe-as-possible interaction with people who are just trying to do their jobs: gas-station attendants, grocery-store clerks, baristas and everybody else. So if you do visit one of the properties below, exercise patience, embrace solitude and be generous and grateful to those who are hosting you.
Midwest
Canoe Bay
Chetek, Wisconsin
Vibe: A kid-free, all-cottage resort tuck.
What you’ll do: If laying on a couch and watching winter go by from beneath a quilt doesn’t appeal (it should appeal), there’s always snowshoeing, nearby downhill skiing and ice fishing.
Your room: The private tiny houses aren’t that tiny (400 square feet), with a sizable porch and lakeside views.
Northeast
The Point, Saranac Lake, NY
Vibe: Super (country) clubby mountain resort in the foothills of the Adirondacks; everything smells like pine trees and gin and tonics.
What you’ll do: Bundle up for hikes through the Great North Woods, cuddle up for movies in front of the fireplace, and definitely drink up — the Point is all-inclusive, which will permit an extremely merry situation at the lakeside ice bar.
Your room: Imagine if the Rowing Blazers vibe had been made into an upmarket guest suite, and you’d have The Boathouse, with a collection of sail-ready nautical flags, views over Upper Saranac Lake and a seasonally appropriate fireplace.
Twin Farms, Barnard, Vermont
Vibe: We haven’t stayed at every hotel in Vermont, but we’re pretty sure it’s the best — thanks to its endless calm, aggressively wonderful cheese plates and plush, haute-rustic decor.
What you’ll do: We’ll nap, play checkers, and roast ourselves in front of the fire — you may want to snowshoe, ski, or ice skate, hot toddy in hand, on Copper Pond.
Your room: The four-bedroom farmhouse would do the Succession fam nicely: there are four suites (so a highly customizable degree of privacy), plus two, separate fireplaces for huddling by warring factions.
Wolf Cove, Poland, Maine
Vibe: This 19th-century inn on the shore of Tripp Lake is here to resolve any latent desires for the ultimate experience in winter cozying.
What you’ll do: Sleep soundly for the first time since 2019.
Your room: The Eagle’s Nest Cabin is the only room to have a private entrance, as well as a walk-in shower and views of the lake and a pine grove.
Rocky Mountain
The Ranch at Rock Creek, Philipsburg, Montana
Vibe: Re: how everyone’s moving from Silicon Valley to Montana: This is where they went on vacation before they decided to leave the 101 behind forever.
What you’ll do: “On-ranch” activities include cross-country skiing, horseback riding through snowy woods, sapphire mining and exclusive appearances from Santa and related holiday luminaries.
Your room: The Trapper Cabin is the most isolated accommodation, with an outdoor soaking tub, wraparound deck and private fire pit. The Ranch can also arrange private jet charters from select airports (in California, New York, Florida, and Texas).
Amangani, Jackson, Wyoming
Vibe: Aman’s trademark zen-minimalism, at one of the chic-chic brand’s two U.S. locations (the other is in southern Utah).
What you’ll do: Snowshoeing across the rugged Wyoming landscape in search of meaningful moments in the company of local wildlife (think: bison!), dog-sledding, and of course, downhill skiing in nearby Jackson Hole.
Your room: A 800-square-foot Amangani Suite has views of the Tetons along with everything else you’d expect (gas fireplace, massive tub, even more massive balcony, etc.).
Triple Creek Ranch, Darby, Montana
Vibe: Where Kevin Costner’s character on Yellowstone would take his new wife, if she were a 35-year-old European aristocrat — which is to say, a solid mix of the ranch life and advanced-epicurean taste.
What you’ll do: Dog-sledding and snowmobiling for the active types, while the sensorially minded might just want to arrange an in-cabin massage.
Your room: The private one-bedroom Osprey cabin has a wood-burning (not gas!) fireplace, plus a private hot tub (and drinks are included in the room rate).
Cabin at Dunton Hot Springs, Dolores, Colorado
Vibe: If you had a friend who fled New York for a better life in Colorado, he might have been envisioning living at Dunton Hot Springs: a five-star resort that looks like the best little mountain town there ever was (and is in fact built on an 1800s ghost town).
What you’ll do: Dunton actually offers a “Winter Wonderland” experience that includes cross country skiing, snowshoeing, ice skating and horse drawn sleigh rides. (Or stay indoors with a cup of hot chocolate.)
Your room: The Well House has a private hot spring and cold plunge pool — the height of the bathing experience at the moment.
Red Mountain Alpine Lodge, Ridgway, Colorado
Vibe: Possibly the ultimate in skier’s delight within the borders of the United States of America.
What you’ll do: Did we mention the skiing? If you’re not comfortable barreling down 13,000-foot peaks, reach out to the guides at San Juan Mountain Guides for local insight and instruction.
Your room: For the ’20/’21 pandemic-era ski season, Red Mountain is only available as “whole lodge” reservation, with a two-night minimum.
Smith Cabin, Aspen, Colorado
Vibe: When Aspen’s a-ight but you’d prefer something a little more exclusive, there’s Smith Cabin, up up up on national forest land, on the back of Aspen Mountain.
What you’ll do: Literally whatever you want, especially if it ends in “skiing”: backcountry skiing, cross-country skiing, cat-skiing — and then snowmobiling, getting married or passing out following a day of high activity on the deck.
Your room: You’ll be all by yourself up here, with up to eight of your nearest ‘n’ dearest — whoever you can fit into the three bedrooms, 11,000+ feet up.
South and Mid-Atlantic
Blackberry Farm, Walland, Tennessee
Vibe: A sprawling farmstead (with five-star appointments) tucked into a corner of the Great Smokies.
What you’ll do: Carriage rides followed by moody walks across misty fields (populated chiefly by wooly white sheep) — followed, obviously, by dinner at the resort’s award-winning restaurant, The Barn, which leans heavily into local, “Foothills” ingredients (think: country-fried sweetbreads with marinated muscadines).
Your room: The Farm House was made from materials taken from a 19th-century Pennsylvania barn, ensuring that the three-bedroom spread comes by its rustic-chic vibe honestly. There’s a kitchen … and on-site chef service.
Primland, Meadows of Dan, Virginia
Vibe: If you’ve ever hiked through the Blue Ridge mountains and thought: I want to do this again, but on Frette sheets — this is your place.
What you’ll do: Past winter activities, sure to be adapted for social distancing, have included tastings of s’mores and scotch (not together). Or, forget all that and head to the woods to hunt pheasant, chukar and/or quail.
Your room: Though Primland has lodging for eight-plus people, two-person parties will do well in the Cottontail mountain home, built in the spirit of a tobacco barn, with cedar floors, a copper tub and a widow’s-watch deck.
The Gasparilla Inn, Boca Grande, Florida
Vibe: When you love Florida, in all its delirious magnificence — but want to steer clear of the larger resorts for now.
What you’ll do: Golf under the palm trees? Kayak through the surrounding bayou? Or charter a boat and head out from “the tarpon fishing capital of the world”?
Your room: Gasparilla recently debuted their Old Florida-style Sharp Houses, with three- or four-bedrooms, and an open invitation to any pets who don’t like missing out on vacation.
Sea Island, Sea Island, Georgia
Vibe: If all you want out of life is beautiful weather, pool(s) for your kids, and non-stop golf, Sea Island would like to welcome you to its all-encompassing loveliness (and a notably friendly and accommodating staff).
What you’ll do: We mentioned the golf, the pools, the weather — let us not forget a range of activities that runs from biking, boating, and bowling to … falconry. (They have basically everything.)
Your room: In a lovely two-bedroom cottage “decorated in calming tones reminiscent of driftwood and sand dollars.”
Southwest and Texas
Inn of the Five Graces, Santa Fe, New Mexico
Vibe: Truly one of our favorite hotels in the U.S.: a luxury take on the Southwest that’s seamlessly accented by antique treasures from Central Asia.
What you’ll do: The only urban (and “urban” is used with some flexibility in genteel Santa Fe) hotel on this list, the Five Graces is a good launching pad for exploring the wider surrounding wilderness — try a hike into the Santa Fe National Forest, like the Atalaya Mountain trail.
Your room: We mentioned the decor, which deserves the wide-ranging press it’s earned in design mags. The two-bedroom suites have mosaic-tile bathrooms (with walk-in showers) plus killer views of the Sangre de Cristo Mountains.
Sanctuary on Camelback, Paradise Valley, Arizona
Vibe: Less luxe-y and eclectic than the Five Graces, the Sanctuary has a more active environment but maintains a deep connection to the gorgeous surrounding landscape of the Southwest.
What you’ll do: Like Sea Island, Sanctuary offers an exhaustive assortment of activities, including golf, tennis and kayaking the Salt River. The spa is also open, with temperature checks for clients, air filters in treatment rooms and additional time between appointments.
Your room: Villas, like Villa Mesa, offer multiple bedrooms, private kitchens, a furnished patio and terrific views.
Wildcatter Ranch, Graham, Texas
Vibe: High-end ranchin’ in the North Texas Hill Country.
What you’ll do: Practice clay shooting and archery – or learn to throw a tomahawk. There’s also a new rifle and pistol range … or horseback riding trails, if that’s more your thing.
Your room: OT’s Cabin is a huge, private space, complete with your own kitchen, that’ll make you feel like you just inherited a ranch.
West
SingleThread, Healdsburg, CA
Vibe: As close as we can get to a high-luxe Japanese inn ATM.
What you’ll do: Come with an empty stomach, write long and detailed entries in your food journal, and luxuriate in the majesty of the meals prepared by chef Kyle Connaughton, whose cooking resume includes time in Japan, and in Heston Blumenthal’s Fat Duck Experimental Kitchen.
Your room: The 700-square-foot Master Suite has a soaking tub, Japanese Toto toilet and a private balcony.
Chateau du Sureau, Oakhurst, California
Vibe: A soupçon of French refinement dropped into the Sierras a stone’s throw from Yosemite.
What you’ll do: Settle into the European refinement on offer at the Chateau — which comes by its continental graces, if not its name, honestly, having been founded in 1984 by the Austria-born Erna Kubin-Clanin. (In short: eat as much as possible.)
Your room: The Villa du Sureau looks, in fact, like a lost mountain home, imported from the Alps, if it was owned by a member of the aristocracy — it offers 2,000 square feet of privacy, with salon, library and marble bathroom.
Sheldon Chalet, Talkeetna, Alaska
Vibe: Haute living in one of the last wild places in the U.S. — and marvelously situated on a nunatak (rock outcropping) on Denali’s Ruth Glacier.
What you’ll do: Settle in for the northern lights in high luxury, after an afternoon trekking across the glacier.
Your room: The five-bedroom Chalet package includes round-trip helicopter sightseeing flights from Talkneeta or Anchorage, guided adventures, a sauna and views of Denali.
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