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January is the right time for decluttering, hitting the gym and planning holiday travel. I know, I know, winter holidays have just faded into the rearview, but if you like to travel with miles and points, now is when you want to book for November and December 2019 holiday travel. If you’re lucky, you may be able to tie down getaways for next Thanksgiving, Christmas and New Year’s — all with miles and points!

Most hotel loyalty programs allow you to book rooms 11 to 13 months in advance, and since standard rooms can generally be booked with points as long as they are available with cash, you want to strike early during peak seasons. Airline booking schedules are a bit more variable, but traditional US programs allow you to book around 11 months out, which currently takes you to about a week before Christmas 2019.

Just when you thought it was safe to put away the holiday planning.

Book New Year’s Eve 2019/2020

If you want to spend New Year’s Eve 2019/2020 somewhere fabulous, you probably aren’t alone in that quest. As of right now, you can book New Year’s Eve at the Park Hyatt New York (30k Hyatt points), the Confidante Miami Beach (15k Hyatt points), Park Hyatt Paris Vendome (30k Hyatt points), St. Regis Aspen (60k Marriott points), Westin Maldives (60k Marriott points) or the Walt Disney World Swan and Dolphin (50k Marriott points). I can virtually guarantee that as the holiday dates near, these options all will either disappear or become significantly more expensive with only premium rooms offered at higher award rates.

We rang in 2019 at Hyatt Lost Pines near Austin.

Book Holiday Ski Travel

As we discussed in the recent Miles Away podcast, if want to ski next winter on points, now is also the time to get to booking. Some booking windows, like with the World of Hyatt, already extend into February 2020, but others at least go into early January 2020. Right now there is pretty good peak ski availability at the Park Hyatt Beaver Creek for 30,000 points per night. If you don’t snap up award rooms while they are there, expect to pay $1,000+ per night with cash.

The DoubleTree Breckenridge is currently just 37,000 Hilton points per night for the week between Christmas and New Year’s (that rate will shoot up). Remember you can leverage your Hilton elite status from cards such as the Hilton Honors American Express Ascend Card to book five standard award nights for the price of four.

Consider also the Westin Snowmass that has many dates around New Year’s Day 2020 available for 35k Marriott points per night. The Hyatt Place Keystone is 15k Hyatt points per night and the Vail Marriott or the Hotel Talisa in Vail are also available at 60k Marriott Rewards points per night. Both of those Vail properties still have good standard availability around next Christmas and New Year’s.

Stay near Breckenridge for just 37k Hilton points if you act quickly.

Book 2019 Thanksgiving and Christmas Break

Maybe your family wants to visit the Christmas Markets in Vienna, brave Disney during the holidays, snorkel in Hawaii or visit Grandma and Grandpa. If that travel is set to happen during the 2019 peak Thanksgiving or Christmas Week, make time to peek at both flight and hotel options ASAP. While hotel availability generally only gets worse for peak days, award flights can be all over the place. Start looking now, but keep checking if you don’t see something that works for you.


Spend the holidays in sunny Cancun (image courtesy of Shutterstock)
Spend the holidays in sunny Cancun. (Image courtesy of Shutterstock)

Bottom Line

The award travel booking world requires you to (try and) live in the moment, but also always keep an eye tuned to what is happening almost a year in advance, especially if you want to maximize your miles for family travel. Last-minute award steals can happen, but families with set travel dates during peak seasons are best served planning trips well in advance. As for me, New Year’s Eve for 11 months from now was just booked using hotel points to stay on the slopes and Thanksgiving Week was booked weeks ago for a tropical paradise family getaway. Those plans can and may change, but jumping ahead of the curve with refundable award reservations has been a solid plan of mine for years.

The Business Platinum® Card from American Express

Aside from the 75,000 points welcome bonus, Amex recently made huge improvements to the Business Platinum Card, including the fact that you will now earn 50% more points on purchases of $5,000 or more, earn 5x on flights and eligible hotels at and cardholders will receive a $200 airline fee credit each year.

Apply Now
More Things to Know
  • Welcome Offer: Earn up to 75,000 Membership Rewards® points.
  • Earn 50,000 Membership Rewards® points after you spend $10,000 and an extra 25,000 points after you spend an additional $10,000 all on qualifying purchases within your first 3 months of Card Membership.
  • Get 5X Membership Rewards® points on flights and prepaid hotels on
  • Get 50% more Membership Rewards® points. That's 1.5 points per dollar, on each eligible purchase of $5,000 or more. You can get up to 1 million additional points per year.
  • 35% Airline Bonus: Use Membership Rewards® Pay with Points for all or part of a flight with your selected qualifying airline, and you can get 35% of the points back, up to 500,000 bonus points per calendar year.
  • Enroll to get up to $200 in statement credits annually by getting up to $100 semi-annually for U.S. purchases with Dell. Terms apply.
  • Get one year of Platinum Global Access from WeWork. With this membership, you can access 300+ premium, inspiring workspaces in 75+ cities. To get this exclusive offer, enroll between 2/15/2019 and 12/31/2019.
  • Terms Apply
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Editorial Disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

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