Our Favorite Fall Getaway Hotels Under $300

When the weather turns crisp and tourists fly back home, Europe returns to the locals. Join them in Rome with a stay at Hotel Stendhal, a tranquil townhouse that’s just a five-minute walk to the Spanish Steps and Trevi Fountain. There’s no spa or restaurant on site, but a library and bar welcomes guests with a free breakfast buffet and light canapés served during aperitivo hour. The 30-petite accommodations are equally inviting with a subdued color palette and classic furnishings (cane-backed chairs, cherry-stained headboards) that make them the perfect landing pad for a crash course through the Eternal City.

It may seem ridiculous to visit Nantucket outside of summer, when swimming is not for the faint of heart, but autumn getaways are just as appealing: think desolate beaches, cozy fires on cool nights, and brisk afternoons that are best spent at places you wouldn’t otherwise see, like the Nantucket Whaling Museum. Sink into a waffle-knit kimono at 21 Broad Hotel, a Victorian-style boutique where the beachy vibe skews modern thanks to a cheerful white-on-white pattern accented with bursts of orange, yellow, and blue. Feeling adventurous? Bike past windswept dunes on your way to Sankaty Head Lighthouse, then post up at the Grey Lady for fresh-caught seafood in a moody setting without the crowds.

Located within walking distance of Montreal’s Old Port and the Notre Dame Basilica, Hotel William Gray is an elegant juxtaposition of the city’s past and ever-evolving present. In the fall, golden light bathes changing leaves, creating a stunning backdrop for the modern décor (think concrete ceilings, black-metal lighting fixtures, and generous windows) now housed in two 18^th-century private homes overlooking the Place Jacques-Cartier. Start your day on a running tour of the neighborhood’s historic streets (groups depart from the reception desk each morning), or with espresso at local favorite Café Olimpico. And be sure to head back to the hotel for a diverse supper (burrata with fig and raspberries, jerk-marinated Cornish hen) at Maggie Oakes before a nightcap at the rooftop lounge.

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A stay in Florida’s ultimate beach playground for under $300? It’s possible at the Freehand, a quirky hotel that feels like summer camp for hipsters. Bring friends to stay in one of the shared rooms, which feature ship-shaped bunk beds and bright throw blankets, or splurge for a private room with a Deco-inspired bathroom and flat-screen television. Rent a bike to take in the shores of South Beach, just two blocks away, or browse the shops on Lincoln Road, then park yourself under a yellow umbrella around the pool before sipping sundowners at the Broken Shaker, the on-set cocktail bar that is quickly reaching cult-status for its farm-fresh concoctions and see-and-be-seen vibe.

There’s no better time to visit California wine country than in the fall, when harvest season brings with it bottling parties and grape-stomping festivals. At the Applewood Inn, set on six-acres of orchards and gardens in nearby Guerneville, you can sip local reds from the hotel’s acclaimed on-site cellar around a babbling fountain, or hop in a car to taste your way through the Russian River Valley’s best vineyards and farm-to-table restaurants. The next morning, a breakfast of Grand Marnier French toast and house-made granola will revive you for another day among the grapes, though no one would fault you for indulging in a deep-tissue massage before you go.

Charleston’s Low Country charms are still in full effect after Labor Day, and the Elliott House Inn is perhaps the best place to experience them. The historic 1861 residence is the portrait of southern hospitality, with 26 newly renovated rooms behind a pastel façade, a tranquil leaf-backed courtyard, and nightly wine and cheese receptions. But the real draw is the inn’s laser-sharp focus on the past. Antebellum buffs will love in-house historian Neal Cook’s customized walking tours of the city; free bike rentals are available for more leisurely excursions. And should you return to your room winded from the day’s activities, room service (think southern classics like shrimp and grits) is available from 82 Queen nearby.

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Even the dogs get the VIP treatment at this family-friendly resort, located in Beaver Creek. Though winter is arguably the best time to visit the region’s snowcapped peaks, there’s plenty to do in the off-season, including whitewater rafting and scenic river floats for even the youngest adventure seekers. The heated outdoor pool makes swimming an option on chilly days, and the kids club keeps little ones occupied so adults can relax with a pine-scented massage at the spa or feast on tacos prepared with fresh-made tortillas at Mexican kitchen Maya.

Sweltering in the summer, overrun in the winter, New Orleans is just right in the fall, when the weather mellows and the party crowd is still in class, and you can wheel around the picture-perfect houses of the Garden District without breaking too much of a sweat. The Ace Hotel New Orleans, an affordable gem in the up-and-coming Arts District designed by Roman & Williams, is almost too pretty to leave, but you’ll be close enough to walk for beignets in the French Quarter, hop on the iconic St. Charles streetcar, or take in a jazz set at Preservation Hall. If that sounds too ambitious, you’re welcome to stay put: at the Stumptown café or oyster bar, in the Stumptown café, in the rooftop lounge, or at Josephine Estelle, an Italian restaurant with a Southern twang helmed by James Beard Award–nominated chefs.