When to Book Hotels for Christmas, New Year’s and Thanksgiving Travel

When to Book Hotels for Christmas, New Year's, Thanksgiving Travel


When should you book hotels for Christmas, New Year's and Thanksgiving travel? TravelSort reader Sam writes “We were disappointed not to be able to book our first choice hotel, the Four Seasons Maui at Wailea, for Christmas this year. When should we book Hawaii for Christmas or Thanksgiving, 2015?”

While I'll use Sam's question for this post, I can't tell you how many readers and clients have been disappointed this year to not be able to book somewhere because they only started thinking about Christmas travel in May, after the best luxury hotels and resorts in popular warm weather destinations such as Hawaii and the Caribbean were already booked up and had long wait lists with virtually no chance of getting in.

Plan Now for Thanksgiving, Christmas and New Year's Eve 2015 

To quickly sum up: if you know you want to get away to a warm weather luxury hotel for Thanksgiving, Christmas or New Year's next year (2015), the time to plan is NOW. You can already book hotels for Thanksgiving 2015 travel, and in a few weeks you'll be able to book hotels Christmas / New Year's 2015-2016.


But We're Not Sure Where/When We Can Get Award Tickets…

One issue that comes up is that for those trying to use miles to get to their destination, many U.S. frequent flyer award booking calendars won't open for the outbound until around 331-338 days out, whereas hotels will generally allow you to book 1 year out and sometimes more, depending on the property.

Festive season bookings for the top luxury hotels often require deposits at time of booking, so should you go ahead and book, paying this deposit, even before you know whether you can get award seats?

As always, the answer depends on your situation: if you plan to go to the destination regardless, and are trying to use miles but will buy paid tickets if you have to, then you'll definitely want to book the hotel, at least at a refundable rate where you can get your deposit back in case your plans change.

If where you go depends on where you can get award tickets to, it's a harder question, since you may need to hedge and book two or three hotels, paying deposits, then later cancel the reservations you don't need. That will tie up some money now in terms of deposits, but buys you options that you may not have later if you wait.


Note the Minimum Stay Requirements

Here are the minimum stay requirements for the most popular resorts TravelSort clients ask about for Christmas and New Year's travel:

  • Four Seasons Maui at Wailea: 7 night minimum between the dates of December 19 – January 4
  • Four Seasons Hualalai: 10 night minimum, which must include the dates of December 24 – January 1
  • Amanyara: 10 night minimum between December 19 – January 5
  • Parrot Cay: 10 night minimum between December 20 – January 3
  • Rosewood Mayakoba: 7 night minimum between December 20 – January 3
  • Amanpulo: 7 night minimum between December 20 – January 5

Not a Regular? Get on the Wait List 

At most of these popular resorts, guests who are in-house for the current festive season receive first priority in terms of reservations for the following year: they can opt to return and lock in their reservation as they depart. Many of these folks have been coming for years, so there can be virtually no space for anyone new, particularly somewhere such as Four Seasons Hualalai.

The best you can do is to put your name on the wait list early. If you're a TravelSort Client, contact me to find out the wait list policies for the particular resort you're interested in, and also the Virtuoso or Four Seasons Preferred Partner benefits for the resort.


Consider a Less Popular Destination

It's no surprise that Hawaii, the Caribbean and Mexico are the focus for guests from the northern U.S. and Canada, given their proximity. But if you expand your scope, for example to Southeast Asia, you can find some warm weather destinations that aren't quite as booked out as the most popular ones in Hawaii and the Caribbean. Sure, it may technically be rainy season in some places, but there's often quite a bit of sunny warm weather as well, after the daily showers. You'll also generally find higher levels of service than the Caribbean, in particular, and better value for money.


Expect to Pay the Full, Non-Refundable Amount of Your Stay by September 1

Most resorts will charge a 2 night or more deposit at time of booking, and have various dates for when the remaining balance is due. Virtually all of these resorts make your full stay amount non-refundable after September 1, so you'll need to have locked down your plans by then or be willing to forfeit the entire amount of your stay.


If You Can, Travel During Another Off-Peak Time and Stay Close to Home for Christmas / New Year's

It's not surprising that the winter holiday is a popular time to get away–it's cold in the northern U.S. and Canada, people are taking some time off from work, kids have 2 weeks off from school, and many people want to be someplace warm with loved ones. 

But since everyone has the same idea and demand is so high, prices are as well, and both flights and resorts are far more crowded than other times of year. If you can travel during an off-peak time, you can pay much less, not face minimum stay requirements, and also have a much better chance of an upgrade, whereas during these times you'll be in the accommodation you booked since the resorts will be booked out…and that's if you're lucky enough to get a booking in the first place.

If you're planning a warm weather vacation or Thanksgiving or Christmas 2015 / New Year's 2016, which hotel or resort do you hope to book?

Related Posts

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Honeymoon in Hawaii: Which Island and Which Hotels

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