What Are the Cheapest Ways to Go on the Most Expensive Vacations?

Beth Stebner
holiday travel deals

(Getty Images/StyleCaster)

Conventional wisdom says that the best (and cheapest) times to travel are during the off-season, but that might mean putting up with blizzards or hurricanes, which doesn’t exactly sound like much of a vacation.

But for most warm-weather destinations, traveling off-peak makes little difference, save in the price. According to Laurel Greatrix, who works with TripAdvisor Vacation Rentals, you can save more than $8,000 by traveling to St. Barts in November instead of late December, based on the cost of an average vacation rental unit during those two months. “Plus,” she adds.” you’re getting way more space and amenities than you would in a hotel.” Or, by renting a vacation home on St. John in the U.S. Virgin Islands in early November as opposed to late December, you can save an average of $3,000.

Another way to get the best deals? If you’re feeling lucky, a last-minute flight or hotel booking could do the trick.

“Sometimes, a property manager will have an empty week for a fast-approaching date,” she says, noting that they’d rather make a little money than no money at all. And that means deep discounts for you.

The safer option for non-adrenaline junkies is to plan early. If you have your heart set on a trip to Machu Picchu and have a set time that you can go, set an alert on a price-watching app like Hopper, which will monitor airfare for you and tell you whether to buy or to wait. It may not be as cheap as flying in the off season, but by booking several months in advance, you have the benefit of time to know you’re getting the lowest price.

MORE: The Best Travel Apps for Your Next Trip

The Galapagos Islands, another high-ticket option, requires extreme amounts of planning because the islands are accessible only by boat (they sit about 600 miles off the coast of Ecuador). Country specialist Arden Dibble of Audley’s says to map out your trip at least a year in advance to get the best rates—and guarantee your spot. “Many boats to the island offer early-bird rates,” he says, which can save you thousands of dollars. If you do take a chance on last-minute planning, Dibble advises booking between October and December when most people aren’t traveling because of holidays.

If you’ve got big-budget dreams but not much green, consider visiting an expensive locale such as Thailand in the country’s low season, roughly between March and October. “Weather patterns differ depending on the region, so you’re always guaranteed sunshine as long as you’re careful to plot your route,” Lauren Burzalow, also with Audley’s, says. An added perk?

MORE: The Procrastinator’s Guide to Last-Minute Travel

“By traveling in the low season, you’ll get killer deals on hotels and shorter lines everywhere.” And the sanity you save is an added bonus.

Another thing to consider: location. “If you’re looking to save, consider a place that’s a little farther away from central locations,” Greatrix says. That means if you’re going to Paris, you probably shouldn’t look for an Airbnb or hotel that overlooks the Eiffel Tower. Use that as an opportunity to explore less touristy parts of the city and stay in a lesser-known arrondissement.

And finally, if you have your heart set on pricey places in Europe—say, London, Stockholm, or Zurich, the off-season really is your best bet, since peak tourist season is in the warmer—and less rainy—spring and summer months.

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