Perhaps the easiest way to lure a New Yorker outside of the city is to promise peace, quiet, and minimal contact with strangers. At Six Bells Countryside Inn, in the small upstate town of Rosendale, located directly on the shores of Rondout Creek and featuring 11 rooms (yes, just 11!), intimacy and quaint charm come naturally. Opened only last year by the Wing’s Audrey Gelman, the inn pairs English-country-house sensibilities with Hudson Valley ease, filling its rooms with antique furnishings, layered textiles, floral prints, and a gently worn, lived-in elegance. Its restaurant, the Feathers Tavern, has quickly become a destination in its own right, serving comforting fare in a warm and inviting setting. Do not leave without ordering the potato croquettes. And that’s an order! (thesixbellshotel.com) —Carolina de Armas

No one has ever checked into the Madonna Inn by accident. Built in 1958 by contractor Alex Madonna, who had strong opinions and absolutely no architect, this 110-room fever dream in San Luis Obispo, California, has spent nearly 70 years daring you to call it tacky. Each of the rooms is its own maximalist conviction: pink granite, cowboy kitsch, flocked wallpaper, and carved wood. Its restaurant, Gold Rush Steak House—all wagon-wheel chandeliers—serves steaks in a room with enough crimson velvet to upholster a theater. And yet, generations of Americans have come here not despite its eccentricities—and downright aversion to good taste—but because of them, which serves as a reminder that originality, even at its most excessive, never really goes out of style. (madonnainn.com) —Jennifer Noyes

Situated in New Orleans’s Marigny neighborhood, Hotel Peter & Paul occupies a former 19th-century Catholic church, schoolhouse, convent, and rectory. Each of its 71 rooms is unique, featuring a palette of colors derived from religious paintings from the 14th-to-18th centuries and combining aesthetic influences from the American South, Sweden, Italy, and France. (In other words, you’ll be e-mailing your interior decorator with the subject line “URGENT” as soon as you get your key.) Did I mention that all furnishings are either curated antiques or designed and constructed locally by regional artisans? With its soon-to-be-opened pool, boutique, and seasonal restaurant, the Elysian Bar, Hotel Peter & Paul is the cherry on top for a visit to NOLA. (ash.world) —Gracie Wiener

In certain pockets of Nevada, far from the casinos, time stands still. One such place is the Gold Hill Hotel & Saloon, on Main Street, a mile south of Virginia City, which flung open its doors under the name Riesen House in 1861—as the Civil War brewed many miles east. Today, guests can follow in the footsteps of Mark Twain (a frequent guest) and stay in rooms within the original stonework, decorated in period antiques, or in the newer outbuildings since erected. Room 4—Rosie’s Room—is said to be haunted by a former lady of the night: guests have reported a lingering scent of roses when none are present. The Crown Point Restaurant and Gold Hill Saloon complete the picture, offering steaks, shrimp scampi, two woodburning fireplaces, and, perhaps, the distinct sensation that someone, or something, is watching. (goldhillhotel.net) —Elena Clavarino

The Red Lion Inn has been welcoming guests since 1773, which means it pre-dates the country whose nostalgia it now so perfectly embodies. Located at the center of Stockbridge, Massachusetts, the inn rises from Main Street in a jumble of porches, gables, and white clapboard, looking much as it has for generations. Rocking chairs line the front porch. Inside, the floors creak, the hallways wander, and every room seems to contain at least one object with a story attached to it. In December, wreaths and twinkling lights transform the inn into a New England fantasy. In autumn, the Berkshire Hills provide a backdrop so picturesque it borders on implausible. Yet the Red Lion’s appeal extends beyond its setting. Nearly 250 years on, it remains one of the country’s most persuasive arguments for slowing down and staying awhile. (redlioninn.com) —Rip Noyes

There are few places in America that have escaped the modern world entirely: Cumberland Island is one of them. Accessible only by private ferry off the coast of Georgia, the island is home to 18 miles of untouched beach, wild horses, salt marshes, and hiking trails lined with massive oak trees. (You might be familiar with its tiny chapel, which held J.F.K. Jr. and Carolyn Bessette’s wedding.) At the center of it all is the Greyfield Inn—Cumberland’s only hotel—which was built in 1900 as a Carnegie-family retreat and converted to an inn in 1962. Without any Wi-Fi offering, staying here truly feels like a trip back in time in the best possible way. The three-course dinners prepared with ingredients from the inn’s own garden (jackets required) and an honor bar that makes the evenings feel like a house party that never has to end are just the icing on the cake. Did I mention there’s no Wi-Fi? (greyfieldinn.com) —Catherine Scott