We know: It seems crazy to even think about the holiday season in May, never mind plan it. But hear us out. Hotels fill up way faster than you think. In fact, most are booked solid by July. So while your family gathers for Memorial Day weekend, start talking about where you want to go in December. Read below for some places that have availability and still-reasonable rates—plus our pointers on how to book smart.

To check real-time availability and pricing, visit our 6 Places You Should Book For the Holidays Now Collection

By Jes Ware

DON’T HAVE A SAD CHARLIE BROWN CHRISTMAS VACATION

What you need to know about the “Festive” season:

  • Most hotels require a minimum stay for bookings during the holidays.
  • Rates are at a premium—and only get higher the later you book.
  • Expect to pay a non-refundable deposit.
  • If a hotel shows as unavailable on Skylark, it might still have rooms set aside offline. Get in touch with one of our agents and we’ll see what we can do.
  • A great way to cut down on expenses: book with another family and split a villa.
  • If you enjoy your stay, book for the following year when you check out.
Belmond La Samanna—St. Martin

WHERE TO GET A HOLIDAY TAN

BELMOND LA SAMANNA, St. Martin

What it's like: The Côte d’Azur on vacation in the Caribbean.

Why we love it: Belmond La Samanna has an easy charm, pinch-me views from the balconies, and a terrific staff. They’re professional and on it, but will never hover or judge your flip-flops.


HACIENDA ALTAGRACIA, Costa Rica

What it's like: A tropical vacation with an adventurous accent.

Why we love it: A luxury lodge with horseback riding, ultralight flights and more, Hacienda AltaGracia is only $5,300 for two people for five nights, including airfare—an amazing deal this time of year.


HALF MOON, Jamaica

What it's like: Colonial chic on a private beach.

Why we love it: Half Moon is consistently named one of the best resorts in Jamaica for a reason. It’s got great golf, a spa, an equestrian center, the best restaurant on the island and sprawling rooms steps from the sand.

Snowmass Village, Colorado

DREAMING OF A WHITE CHRISTMAS?

ASPEN AND VAIL, Colorado

What it's like: A storybook setting for a classic holiday.

Why we love it: Everyone knows the powder in the west is the best. Both Aspen and Vail are at their peak during the week between Christmas and New Year’s. And both are showing plenty of availability right now—but it’ll go fast.


THE ALPS

What it's like: Family-friendly, with a stylish je ne sais quoi.

Why we love it: There are so many ways to do the Alps: Courchevel is for avid skiers, with excellent snow and over 170 lifts. Hotel Le K2 is both top-of-the-line luxe and charming. Mégève is both scene-y and scenic, and Alpaga has easily the best of both, with its incredible views of Mont Blanc. Nearby, the The W Verbier curbs its W-ness in deference to the majestic setting—and as a bonus, it's just steps from the main gondola.


DEER VALLEY, Utah

What it's like: White-glove service and mountains of powder.

Why we love it: Deer Valley has had incredible snow fall the last few winters. Ski-in/ski-out Montage Deer Valley and the champagne-sabering The St. Regis Deer Valley are choice digs that still have availability.