5 Best Fall Vacation Ideas to Book in 2021

A midwest lake town, Elkhorn is an idyllic getaway for city goers looking to admire the changing leaves. Great for families or couples, Elkhorn is brimming with apple orchards, breweries, and walking trails.

Where to Stay:

Listed on the National Register of Historic Places, Wandawega Lake Resort once operated as an overnight camp for kids. Under new ownership, the goal is to turn people onto the simple pleasures of camping. All accommodations—choose from vintage cabins, cottages, or dorm-style bunkhouses—come with a no-frills attitude. There’s even an option to camp out in the woods. Hang out by the lake, dig into a fall read, and enjoy meals at the original dining hall—dating back 60 years—where guests can arrange to have private dinners with renowned visiting chefs from Chicago and beyond.

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Quiet and serene, the Catskills region in southeastern New York State has an abundance of wildlife and greenery, but not without a great culinary scene, handicrafts, and a booming community of artists.

Where to Stay:

Enjoy the Catskills’ fall beauty from Piaule’s new 50-acre property, featuring wetlands and nature preserves with wide open views of the Catskills Mountains and Kaaterskill Clove hiking trail. Formerly a bluestone quarry, the property now houses 24 private cabins, designed with wall-to-wall glass doors and windows so you feel completely immersed in nature. The modernist retreat has a tranquil spa—equipped with a plunge pool—and an onsite restaurant where you can enjoy your morning coffee and dine on locally-sourced seasonal ingredients, then handmade cocktails and local wines come evening.

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Long a popular stopping point for well-worn travelers, Middleburg (located in the, well, middle of a busy trading route circa 1700), is a charming town full of historic relics dating back to the Revolutionary War. Home to 30 wineries, the area just east of the Blue Ridge mountains is also a great fall destination for oenophiles.

Where to Stay:

Surrounded by gardens and an operating farm spanning 265 acres, Goodstone Inn and its accommodations feel straight out of a storybook. An ideal place to unwind after a busy summer season, the inn’s quaint rooms and cottages are individually decorated in romantic French and English countryside decor. At the restaurant, executive chef Jan Van Haute creates dishes that draw inspiration from the hills and farmland, using the inn’s fresh-grown ingredients for a true farm-to-table dining experience.

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Located on the Yucatan Peninsula along the Caribbean coastline, Quintana Roo offers visitors tranquil beaches, cenotes (gorgeous caves with stunningly blue water), and ancient Mayan ruins to explore.

Where to Stay:

Originally built as a private mansion for an Italian duchess, Hotel Esencia now operates as a serene hideaway on the Mayan Riviera. Boasting 42 suites and three villas, the resort recently unveiled a brand new tennis court and a master jungle suite—ideal for summer newlyweds who are looking to take an autumn honeymoon. Spend your days snorkeling and admiring sea turtles, visit the nearby ruins of Tulum and Chichen Itza, and return for dinner at one of the hotel’s restaurants featuring elevated Mexican cuisine.

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Situated in the San Juan Mountains at an elevation of 8,600 feet, Dunton once operated as a 1800s mining town. Restored as a pseudo-functioning mining town reminiscent of its glory days, it’s the perfect place to bask in the serenity of the Colorado wilderness, complete with long winding trails and natural hot springs. We’re calling the vibe “rugged romance”—Lily Collins was just married here!

Where to Stay:

This unique ghost town is now home to Dunton Hot Springs resort, spanning 1,600 acres of untouched wilderness. Travel back in time with a visit to the resort’s saloon and dance hall and rest your head in authentic log cabins decorated with artifacts and antique furnishings evoking the 19th century. Take a horseback ride in the Rocky mountains, hike the San Juan mountains, or go on a rafting excursion along one of the nearby rivers. Alternatively, lay low and spend a crisp fall day at the hot springs and spa. Dunton’s renowned chefs create fresh menus each day and offer signature ranch-style dinners for a full pioneer experience.

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