America’s small towns don’t have the big-city-hustle that you’re used to — and you don’t want them to, either. What they lack in public transit, they more than make up for with charm. These towns are like your favorite cozy sweater—warm, familiar (even if it’s your first time visiting), and always ready to wrap you in nostalgia. They boast diner breakfasts that could cure a bad mood, bookstores where the owner recommends something life-changing, and locals who greet you even when they don’t know you (or pretend not to know you if your parallel parking was questionable). These character-filled pockets of the country, each with its own personality, offer more than just good vibes. They may be small in size, but their hospitality is anything but modest. This is a look into the most charming small-town getaways in the US. And no one said anything about roughing it.
The Town: Charleston, South Carolina
Where to stay: Hotel Bennett
If anyone told you that America doesn’t have enough history, take them to Charleston. This town is seeped in history and southern charm. There are cobblestone streets, pastel mansions, antebellum architecture, and historic homes that look like they’re jumping out of a fairy tale, where Southern belles still host afternoon teas. You will be time travelling to the 19th century. This Southern gem oozes history, hospitality, and a little humidity—but hey, that’s just nature’s way of giving you a free facial. Spend your day sipping sweet tea that’s basically liquid sugar, dodging horse-drawn carriages, and trying to look casually fabulous in the oppressive heat. The food? World-class shrimp and grits, BBQ that could convert a vegetarian, and oysters so fresh they practically introduce themselves. Charleston is old money meets new cocktails, with a dash of ghost stories to keep things exciting.
Hotel Bennett is the place to stay. It was literally built by native Charlestonians, so, authenticity is guaranteed. The hotel also has a rooftop pool with city views and an exclusive lounge called The King’s Club. The dining options are also exquisite, with two restaurants — Gabrielle and Camellias and a French inspired bakery, La Pattisserie.
Charleston itself is recognized as the culinary capital of the South. So, you might want to head out and explore the traditional southern fare that the town offers. Beyond the food, we suggest you explore the Magnolia Gardens, Drayton Hall, Boone Hall, and Fort Sumter to get a glimpse into the region’s past. Fort Sumter is actually the site where the first shots of the Civil War were fired. You can head to the City Market for the local crafts and souvenirs, and then end the day at Waterfront Park, which features the Pineapple Fountain and harbor views. Stay classy, Charleston.
The Town: Big Sky, Montana
Where to stay: Montage Big Sky
Welcome to Big Sky, Montana, where the mountains are dramatic, the air is fresher than your organic matcha, and your après-ski is just as important as your actual skiing. This is nature’s VIP lounge, where cowboy culture meets luxury retreats, and the only traffic jam you’ll see is caused by elk casually blocking the road like they own the place (which, honestly, they kind of do). Big Sky’s skyline is dominated by the Lone Mountain. In the winters, its expansive terrain and uncrowded slopes become a magnet for the skiers. In the summers, it becomes a playground for hikers and campers (you’re right on the doorstep of Yellowstone National Park). You can head to the Gallatin National Forest for hiking, or fly-fish in the Gallatin river. And if camping isn’t really your speed, stay at Montage Big Sky.
Montage Big Sky is all about rugged elegance, and ski-to-door access. The architecture is, of course, mountain-inspired — so you’ll still feel like you’re in the big outdoors. Naturally, there are plenty of dining options to fill up on all the energy you’ll need to hit the slopes again. You’ll feast on bison burgers with a view, and sip cocktails that taste better at 7,500 feet. You can choose the signature restaurant, Cortina, that offers local cuisine from locally sourced ingredients. Or, choose to lounge in Alpenglow — the cozier option with craft cocktails and nibbles. Backcast is their pub that you can ski into directly for a hot bowl of ramen. And the Beartooth Pub and Rec is where you would go for sweet treats and sundaes.
The Town: Aspen, Colorado
Where to stay: The Little Nell
If you’re someone who feels the lack of culture and sophistication in cities today, Aspen is a place that will reinstate your faith. Welcome to Aspen, where the altitude is high and so are the real estate prices. Nestled in the Rocky Mountains, this town is equal parts ski haven and social runway, where the slopes are pristine, and the après-ski scene is practically an Olympic sport. Here, people hit the powder like their hedge funds depend on it, and designer ski gear is considered formal wear. The food? Think Michelin-starred truffle everything, paired with cocktails so exclusive, they practically require a background check. Even the dogs here look like they just walked off a Ralph Lauren photoshoot.
If skiing isn’t your thing, you can still indulge in all the après-ski (they seriously don’t check). But you can also explore Aspen’s roots as a silver mining town in the late 19th century, with remnants of this era still visible. Or, head out to The Wheeler Opera House that continues to be a testament of Aspen’s cultural prosperity.
When you’re in Aspen, stay at The Little Nell. This hotel is Aspen’s social headquarters, where fireplaces crackle, and wine lists impress even the snobbiest of sommeliers. It’s a ski-in/ski-out hotel. They have a fitness center and a spa for relieving you of all the pain you might have incurred from slipping on the slopes. The heated outdoor swimming pool and hot tub are also good for that. For food, The Little Nell is a literal culinary haven. The Ajax Tavern is visible from halfway up the mountains — we can spot their legendary truffle fries even from New York. Element 47 is their nod to Aspen’s history of silver mining and serves the regional cuisine. And for a night cap, don’t forget the Wine Bar and The Wine Cellar for lounging.
The Town: Napa, California
Where to stay: Auberge Du Soleil
On the westernmost front, Napa is the leader of charming small towns. In Napa, your daily step count can consist entirely of walking between vineyards, and nobody will judge you. The wine here flows faster than traffic on Highway 29 — and it’s world class. Here, vineyards stretch farther than your last vacation itinerary, and every tasting room has a sommelier who could talk you into buying a bottle that costs as much as your watch. But as you pretend to know the difference between “oaky” and “buttery,” don’t forget that wine isn’t all there is to Napa. You can hot air balloon at sunrise, soar over rolling vineyards, kayak down the Napa River, pass historic bridges, shop in antique stores and chic boutiques, and try every top-tier farm-to-table restaurant.
When you’re in Napa, stay at Auberge Du Soleil. It’s one of the flagbearers of luxury in the valley — this property literally started the ‘wine country chic’ aesthetic in the area. From almost every window, there are views of the 33 acres of vineyards and olive groves. Of course, they have a series of wines you can taste at The Bar along with cheese and charcuterie. We also recommend having lunch at the Terrace of The Restaurant for Michelin-level Mediterranean cuisine. Beyond the food, the hotel boasts a series of wellness experiences for you and your +1. Try the exclusive after-hours package that is three hours of private garden soak, steam, massage, wine, and dessert under the stars. Not a shabby end to the day, if you’ve spent it hopping from one wine estate to another.
The Town: Jackson, Wyoming
Where to stay: The Rusty Parrot Lodge & Spa
If it’s the wild wild west your heart yearns for, Jackson has it all. The dramatic Teton Range forms the heart of Jackson’s appeal. Jackson is 97% public land, and right on the doorstep of two national parks: the Grand Teton National Park and Yellowstone. So, if your national parks passport is still missing stamps from these ones, we suggest you take a trip this summer. Jackson is your rodeo oyster. We’re talking horseback riding. Fly fishing. Scenic floats. Paragliding. Wildlife tours. A new music venue at the very top of Snow King Mountain. The Grand Teton Music Festival. Basically, the rule is: if you can think it, Jackson probably has it. Jackson is also consistently rated the best ski mountain in North America.
You’re also not short of where to stay in Jackson. The best option is to rent a home from The Clear Creek Group. They manage 82 of some of the highest end rental homes in Jackson. But if a hotel is more your speed, stay at The Rusty Parrot. This one is your boutique hotel in the heart of Jackson. It’s known for its cozy yet upscale atmosphere — it’s charmingly rustic and beautifully modern. The rooms here are equally sophisticated, with Italian linens, fireplaces, and private balconies. Their Wild Sage Restaurant is renowned around the town, serving gourmet, locally-inspired cuisine. And there is, of course, a rejuvenating spa (The Body Sage Spa).
Regardless of where you stay, though, bear in mind that The Clear Creek Group have a concierge team that can make every single one of your Jackson dreams come true. Seriously, try it. If you can think it, they can make it happen.
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The Insider Guide to Napa Valley
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FAQs
Q. What is the best time to visit Big Sky?
A. The best times to visit Big Sky is December-March and July-August.
Q. How can I get a reservation at Amangani?
A. You can drop us a line at [email protected] and we’ll take care of it.
Q. Which national park is close to Jackson Hole?
A. The Grand Teton National Park is close to Jackson Hole.
