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12 Vacations That Get Cheaper in Summer

We don't typically think of summer as the ideal time to visit warm weather destinations but those in the know can find great deals, spectacular weather, and fascinating festivals.

Nisbet Plantation Beach Clubvia


The childhood home of Alexander Hamilton, Nevis is 36-miles of unspoiled paradise located in the heart of the Caribbean Islands. This charming island features chattering monkeys, brilliant starry skies thanks to a lack of streetlights, and the beloved annual Mango & Food Festival in early July. Don’t worry that it will be too hot for you, day time temps in the summer average in the low 80s, only five degrees warmer than during winter’s high season. Once a sugar plantation, Nisbet Plantation Beach Club offers a 48 percent savings for a superior room in summer ($238 double occupancy with breakfast, versus $455 peak season), and in 2019 you can get a fifth night for only $30 as part of its 30thanniversary celebration. As for getting there, last year, flights to Nevis, West Indies made Tailwind’s list of International Summer Travel Steals—and you can always check out our list of the cheapest days to fly in 2019 for more.

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Havana Cabana at Key Westvia

Key West

The southernmost tip of Florida is well known for its picture-perfect beaches and the hordes of spring breakers who flock in every year. While spring may be the most popular time for visitors, it’s the summertime that can be the most pleasant. July through September temperatures reach low 90s and the skies can open up. The upside: crowds leave and bargains move in, with room rates up to 60 percent cheaper than at peak season. The Havana Cabana at Key West Hotel, minutes from historic Old Town, features a tropical décor and 25 versions of mojitos. Winter rates start in the high $400s and can increase during those busy three weeks in the spring, but summer rates average in the mid $200s. Food lovers will want to be in town over Fourth of July for the Key Lime Pie Festival or from August 8 to 11 for the Key West Lobster Festival. If you can’t make either, check out our favorite food festivals across the United States to find one near you.

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CaymanCourtesy The Westin Grand Cayman Seven Mile Beach Resort & Spa

Grand Cayman, Cayman Islands

Grand Cayman is the largest of an archipelago of three islands south of Cuba in the western Caribbean, which is largely sheltered during hurricane season (June 1 to November 30). Even more enticing: in the summertime, flights and lodging are slashed up to 50 percent from peak rates. The Westin Grand Cayman’s Seven Mile Resort & Spa, included on Condé Nast Traveler’s Gold List offers a perfect beach with summer prices starting at $239 a night versus $649 in winter. Dive into the crystalline waters, tour the Cayman Crystal Caves, a onetime pirate lair, and see why Grand Cayman is a foodie capital of the Caribbean.

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BreckenridgeCourtesy Jeff-Andrew

Breckenridge, Colorado

What does one do in a ski resort in summer? Find out in Breckenridge, Colorado. Over the past decade, Breckenridge has morphed into a year-round vacation destination with seasonal activities ranging from 100+ miles of hiking trails, rafting, zip lining, and an exploding culinary scene. A cultural summer highlight is the Breckenridge International Festival of Arts held August 8 to 19 this year. Lodging costs 40 to 60 percent less in summer than in winter. A typical daily rate for Pinnacle Lodging, which manages 160+ vacation rentals, is approximately $150 from June through September, versus $510 in winter.

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Tween WatersCourtesy Tween Waters Island Resort & Spa

Sanibel and Captiva Islands

Located 25 miles north of Fort Myers are “sister” tropical barrier islands Sanibel and Captiva. These islands are connected by Blind Pass bridge—crossing the bridge takes under a minute!—and offer a summer sanctuary: uncrowded white sand beaches, brilliantly bright skies, and substantial summer savings. Sanibel Island is home to the 6,400-acre J.N. Ding Darling Natural Wildlife Refuge, one of the country’s best birding spots and marine scientists at the Sanibel Sea School teach families to interact with aquatic ecosystems, including holding a seahorse, casting a net, shelling, and more. Rates at ‘Tween Waters Island Resort & Spa, a former collection of fishing cottages on 13 beachfront acres in Captiva drop to $225 starting in June—that’s 50 percent off the high season rate. While you’re there, be sure to check out these best Florida beaches locals want to keep secret.

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BarbadosCourtesy The Crane Resort Barbados


During the summer season, Barbados, the eastern Caribbean island, boasts fabulous weather. There are tranquil pink sand beaches, accessible ocean caves, and a lively nightlife. Time your visit to the annual Crop Over Festival, a three-month celebration of traditional and modern Barbadian culture, which usually runs between June and August. The 252-room Crane Beach Hotel, the oldest continually operating hotel in the Caribbean, offers tropical-luxe rooms with private pools, an onsite spa, and 40 percent off through its Summer Bliss Package. Those who seek even more tranquility and seclusions will want to explore our list of the 11 least-crowded islands paradises in the Caribbean.

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Chas HarborCourtesy Charlestowne Hotel

Charleston, South Carolina

Routinely voted as the best city in the country by the readers of Travel & Leisure, don’t let hot summer temperatures keep you from enjoying cool off-season bargains. Bask in a panoramic sunset from a schooner, indulge in James Beard award-winning cuisine at Rodney Scott Whole Hog BBQ, tour historic Fort Sumter, where the first shots of the Civil War were fired, and lounge on the smooth sand beaches of Sullivan Island. Other highlights include the massive centuries-old Angel Oak Tree, 66.5 feet tall and 28 feet in circumference, and the historic open-air City Market for food, crafts, and atmosphere. Make your home base the Harbour View Inn, a waterfront hotel with a private rooftop terrace, with rates starting at $219 in summer, down from $679 in high season.

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MujerCourtesy La Casa Que Canta

Zihuatanejo, Mexico

Expect a quieter vibe in this stunning seaside town perched on Mexico’s Pacific Coast next to Ropa Beach than in beach resorts like Los Cabos, Cancun, and nearby Ixtapa. Starting in July sea turtles begin arriving on the beach to lay their eggs. The 25-suite La Casa Que Canta, named the most Romantic Hotel in the world by Travel & Leisure, drops its winter rate of $435+ a night to $300 from April to October.

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The Halyard Outdoor DiningCourtesy Read McKendree

Greenport, Long Island

While you’re less likely to run into an A-list celebrity as you might in the Hamptons to the south, we recommend you spend your summer vacation in Greenport. This charming 19th-century whaling village on Long Island’s North Fork is dotted with family-run vineyards, quiet beaches, organic farms, a 104-year-old movie house, fresh-off-the-boat seafood, and an opportunity to shuck your own oysters. The recently renovated Sound View, located on a quarter-mile of private beach, has 55 cedar wood rooms that resemble old-time ship cabins, a piano bar, Osprey sanctuary, yoga and meditation classes, and an acclaimed restaurant, The Halyard. Summer room rates start at a very un-Hamptons like price point of $325.

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LexCourtesy VistLEX

Lexington, Kentucky

Known as the “horse capital of the world”—Lexington, Kentucky is home to 400 historic horse farms and counting—this getaway sweet spot is a southern gem tailor-made for an affordable family visit. The Kentucky Horse Park has both a museum and youth riding camp. The Explorium is not just an interactive children’s museum, but also offers an overnight program for the younger set. The Lexington Distillery District is home to a brewery, two distilleries, and a number of restaurants and makes for a fun, walkable evening out. Something else to toast to: The Railbird Festival scheduled August 10-11 will celebrate Kentucky’s musical roots. Rates at Griffin Gate Marriot Resort & Spa start at $249 a night versus $390 in high season.

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Playa GrandeCourtesy Solmar Hotels & Resorts

Cabo San Lucas, Mexico

Perched where the Pacific Ocean meets the Sea of Cortez, late summer is a fabulous time for bargain hunters and serenity seekers to visit “the World’s Aquarium,” Cabo San Lucas. The water beckons for adventurers, particularly surfers, as the waves are most consistent this time of year. Sail around the majestic limestone arch El Arco for a summer breeze and to catch a glimpse of the local sea lions. Landlubbers can explore the desert and beach via horseback, ATV, and camel, or golf on courses designed by greats like Greg Norman. Hike Mount Solmar at sunset, then quench your appetite with amazing seafood and tequila. In summer, a junior suite at Playa Grande Resort, located on eight acres of beachfront, starts at just $168 a night.

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Las LagunasCourtesy Las Lagunas Boutique Hotel Museum & Spa

Flores, Guatemala

If an eco-luxe hideaway jungle adventure an hour from the ruins of Tikal, the UNESCO-protected Mayan pyramid temple complex sounds appealing to you, check out Las Lagunas Boutique Hotel. Spread across 300 lush acres of a private reserve in Northern Guatemala, between Mexico and Belize, each of the property’s 19 lake-top casitas includes a private deck and jacuzzi. In the uncrowded summer “green” season, you’ll enjoy a truly intimate stay replete with a full-service spa, five lakes, birding, zip lining, biking, and the opportunity to take a pontoon tour to Monkey Island to see and perhaps feed spider monkeys. Rates start at $630 for a three-night stay in a Waterfront Queen Suite (normally $945 for a three-night stay). Still deciding? Check out our perfect vacations for every week of summer.

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Every product is independently selected by our editors. If you buy something through our links, we may earn an affiliate commission.

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