Why you should book winter holiday trips now using miles, points


To get maximum value for your rewards, it’s best to book 11 months out for next year’s winter vacation.

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I know that most of us are ready for spring, summer, beach trips and warm weather, but if you like to get the maximum value for your miles and points, your mind should still be on winter. Specifically, you should be thinking about next winter and the trips that you hope to take from Christmas break through spring break of 2019.

This may sound crazy since I know many families are still putting the finishing touches on their spring break trips in the coming weeks and may not have figured out where to go this summer.

While it may be a shift in thinking, my years spent maximizing miles have taught me to think about trips at least 11 months in advance to get the maximum value. If you like to travel during peak travel times, waiting until a couple of weeks or months before your travel date is a recipe for not finding the award flights or hotel nights that you want since availability is limited.

Thinking and booking about a year out is a solid family travel strategy year-round, but it is even more important during the winter, when the popular holiday dates are much more compressed than they are during the long months of summer.

Lock in winter 2019 hotel award reservations

As of today, you can use 20,000 Hyatt points per night to stay at the Hyatt Regency Lost Pines Resort about 30 minutes outside of Austin, Texas, for the family-friendly New Year’s Eve celebration.

On this special night, the resort hosts a carnival, fireworks and all sorts of entertainment. Paid rates for this winter celebration will set you back close to $600 per night. You can book now using Hyatt points, but if prior years are any indication, you will have no option other than to pay cash as the holidays approach.

The same trend will hold true at many hotels that host New Year’s Eve celebrations.

If you want to ski during peak winter dates between Christmas and New Year’s, you currently can have your pick of any of those dates at the slopeside Hilton DoubleTree Breckenridge for 60,000 Hilton points per night. The peak ski dates will sell out at virtually every single ski-friendly property as people turn their eyes toward next season. Don’t wait to book.

The same goes for any ski trips plannned during any of the long winter weekends such as President’s Day weekend in 2019.

Those hoping to flock to warmer weather during next year’s winter break also are competing against many other families with the same idea. A quick search of the major Hyatt resorts on Kauai and Maui shows that standard rooms are all already booked for the week of next Christmas, but you may have better luck with Hilton.

I found availability the week between Christmas and New Year’s using 60,000 Hilton points per night at the Hilton Waikoloa Village on the Big Island or at the Hilton Garden Inn on Kauai. It is only a matter of time before those properties also fill up with advance planners.

Keep an eye on winter flights now

Flights are a slightly different story from hotels since you usually can cancel your hotel award nights without penalty until much closer to the travel date. The same is not true with most flights.

Airlines don’t release all their award flights the second their schedules open, but since the traditional carriers post their schedules about 11 months out, you do want to start looking now. This is especially true during peak winter travel times such as winter break or the long weekends in January and February.

Airline award availability on peak travel dates to popular family destinations generally gets worse as the months roll by. If you see any airline awards you like for next winter, now is the time to lock them in. If you don’t see what you want quite yet, keep checking at least a couple times a week and then act quickly when you find availability before someone else beats you to it.

If you are considering purchasing tickets with cash or using points from a credit card that lets you use points at a fixed value to book travel, such as the Barclaycard Arrival World Elite Mastercard or Capital One Venture card, then I recommend setting some airline price tracking alerts now.

You can set airline price-tracking alerts through Google Flights, SkyScanner or Kayak so you can be kept in the loop on rising or falling prices without having to obsessively remember to check rates. Airline prices may change many times before next winter arrives, but the only way to really know what fares are doing on your desired route is to keep an eye on them via a free airfare tracking tool.

Just like with hotel points, if you hope to use airline miles to travel during a peak time, waiting until the last minute will likely end in disappointment and paying more than you had hoped. Getting ahead of the curve and booking trips that are roughly 11 months out is one of the ways to start increasing the value of your miles and points!

See related:The 3 types of rewards cards you must have in your wallet, Using points to stay at all-inclusive resorts

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