The Ultimate Guide to Planning Your Winter Trip with Points and Miles

Planning your winter trip

Planning your winter trip is a lot of fun, especially when you are this close to winter arriving. Our winter trip is one of my favorites every year, and I’m looking forward to ours this year more than ever. We live in Florida, so we don’t get winter. We get 70s – and we don’t typically complain about that the month or two that we don’t have to sweat (though we are wondering where that weather is right now as the 15 day forecast puts us at 85 degrees on Christmas day and that’s no fun). Our winter trip is one we take in February. We used to do a long trip somewhere fun, such as Lake Tahoe or Aspen or Stowe.

However, we now have for kids and we’ve decided that until the twins are 3 or 4, we are going to enjoy planning our winter trip by ourselves. You see, we don’t mind flying with them, but the babies are so small and quite frankly it’s a lot of work to bundle them up and put them in and out of car seats and strollers – and we can’t do anything with them in the snow (not to mention, they’re not fans as of yet) so we thought we’d just wait until they are a little more enjoyable to spend time in the snow. The beach, Disney, cruise ships – they’re golden. The snow? They’re not ready.

When planning your winter trip, where do you go? We go to New York every February for a long weekend for several reasons. For one, it’s a two hour flight from Florida, it’s a nonstop flight and we feel as if we are getting away but still so close to home. Travel doesn’t wear us out being such a short flight, so we don’t mind doing a three day trip. We aren’t that comfortable being away from the kids much longer than that, so we feel it’s win-win for us right now. Additionally, we love the city. We have favorite places, favorite restaurants and a favorite hotel. We have gotten to know many of the people there since we do go two or three times a year, and we really do enjoy our trips and our customs. And we love that it’s snowing when we get there and it’s always so gorgeous to us palm tree and sunshine and heat-living Floridians.

When planning your winter trip, what do you do to save? Do you use your points and your miles? Do you save up to book your winter trip in this manner to save money or because you travel so much throughout the year it only makes sense to spend a little bit less on this trip? Has planning your winter trip using your miles and points simply never occurred to you? If not, we have some suggestions that might be helpful so that you can plan an amazing winter vacation using your points and miles and save a lot of money in the process. Here’s what you need to know about maximizing your points when planning your winter vacation to the most popular West Coast US ski resorts.

Planning Your Winter Trip Flight

The most important aspect of planning your winter trip is your flight. After all, you’re not getting anywhere without a flight. The mountains across the country are difficult to reach unless you plan on driving – and that does not sound like a boat load of fun at all. Most major ski cities in the US have one small problem; they are not near major airports. This leaves you with two larger problems. You either book a flight to the nearest airport to your destination or you book one to a major airport and then drive.

Here’s the smaller problems within the larger problems; for one, you will not get a direct flight into a smaller airport from most every other airport in the country. Two, you will pay a lot more a flight into a smaller airport – even with points. The other problem is that you can get any number of nonstop flights into major airports, but you then have to figure out ground transportation and add that cost into booking your trip.

Now – figure out which one works more efficiently for you, your points and your out-of-pocket expenses when planning your winter trip. Perhaps you might find a location a bit closer to a major airport so that you can either rent a car or book a cab or limo or hotel transportation for very little, while still using your points to book your flight. It’s likely much more affordable that way.

Ground Transportation

If you’re looking to book a rental car when you land, I will share with you a secret that I have learned in the many trips we’ve taken and needed rentals; Priceline. Sure, you can use your points, but I wouldn’t. I have tried numerous times to use points to book a rental car only to realize that it’s far more affordable for me to pay cash in every situation – even paying full price.

With a family of 6 and the need for a full size SUV in the extra long department, we are very as to what we can rent (and even when we don’t take the twins with us and it’s either just us or just us and our big girls, points and rental cars are never a good deal). We have very little choice other than an XL Yukon or a Suburban, and those are not inexpensive. What I’ve done is learned a great trick; I use to book all our rental cars.

I’ll use my last few as an example. When we took our big girls to our yearly lake house rental with friends and family in Tennessee over the summer, we booked a sedan. Regularly the price was $300 – cheapest of all the Knoxville airport rental locations that week – for the week. We used Priceline to name our own price and got it for a grand total of $120 for the entire week. When we took all the kids to Texas in October to visit my grandmother on her farm, we booked an EL Expedition at the Dallas/Fort Worth International Airport for the five days we were there. The price without Priceline would have been $900 (cheapest I was able to find) but we were able to book for $350 with Priceline by naming our own price.

I would advise doing this because you don’t care where your rental comes from at the airport so long as it is the size you need. I’ve also found that many rental agencies allow you to prepay for your car at a much lower rate than if you pay when you arrive. Whatever you do, don’t waste your miles or points booking a rental car when planning your winter trip this year.


When planning your winter trip, you have to plan for a hotel unless you have a winter home you can stay in while you are there. This is where you will find that your hotel points come in most handy. My advice as a frequent traveler is to do some math before you commit to booking anything. One way to ensure you are getting all that you deserve is to make sure that the price you are paying to stay in a hotel is not more than the price you would save when you use your points to book when planning your winter trip.

For example, there are a number of amazing hotels in cities in Colorado and Utah that offer amazing rewards programs. You could apply for a card from one of them and receive the free points as a sign-up bonus to help you pay for your room. For example, we’re going to use the Sheraton Mountain Vista Villas in Colorado as an example. If you don’t already have the Starwood Preferred Guest card, you can apply for it now and earn 25,000 bonus points spending $3,000 in three months.

The hotel allows you to stay free of charge using points for only 10,000 points per night. That means you’ll get two nights free. Let’s say you want to stay 5 nights in all. We chose a random week in January during which the rate for a premium one-bedroom villa is $284 per night plus taxes. With two free nights, you’re paying a grand total of $852 before taxes. You can also buy more points through SPG; so it’s worth seeing if buying points to make up for the three nights is cheaper.

Now through December 31, all SPG members are eligible to receive up to 25% off the price of points depending on who many you buy. In this scenario, you’ll need 50,000 points for a five-night stay. You have 25,000 points, so you only need 25,000 more. Unfortunately, you can only purchase 20,000 starpoints per year. However, with the holidays here, you spent more than the $3,000 required to earn your sign-up bonus; we’ll say you spent $5,000 paying your mortgage, utilities and Christmas shopping (and paid it all off at the end of the month). Now you have 30,000 points so you only have to purchase 20,000 to get your free nights.

At $.35 per point regularly, you’d spend $17.50 per 500 points. That would equal out to $700 for 20,000 points. However, during the promotion you receive 25% off this price so you’re points would only be $525. That’s a lot less than the $852 you’d pay for the room otherwise. However, it’s not that much savings. Now it’s up to you to decide if it’s worth it to purchase 20,000 points and add them to your existing 30,000 to save just about $300.

Or would it be more beneficial to book a more expensive hotel? Think about it; the savings here is only a little more than $300. It almost seems like a waste of points to save $300. If you paid in full for 5 nights, you’d only pay $1,420. Now, think of it this way; you’re paying $525 for your extra points, so you’re really only paying an additional $900 to book the room using cash.

If you choose the St. Regis Aspen the same week, you get an SPG rate of $854 per night. For five nights, you’re looking at $4,270 for the room. You get a free room when you have 30,000 points. You cannot purchase enough points to get a second night free, so what do you do? It seems like saving one night and booking for only $3,416 is not that much savings at the end of the day.

However, what if you book and use cash and points? With this payment method, you can use 15,000 per night and pay only $275 per night otherwise – that’s a savings of $579 per night. If you purchase an additional 15,000 points during the promotion, too, you will get 20% off your order leaving you responsible for paying only $394 for an additional 15,000 points. You now have 45,000 points to use for three of your five nights. When you do the math, that’s 45,000 points for three nights, plus $275 a night for three nights, plus $854 per night for two nights for a grand total of $2,533; you’re saving $1,737 on the cost of your room this way – and staying at a much more amazing hotel.

Don’t look at the cost; look at the savings. You can use all those points and only save $895 on a nice hotel or you can spend $2,533 (only $2,000 more) for a high-end five star resort and saving more than $1,700 on your trip. Depending on your financial situation and travel preference, either might be a nice choice – but for me the obvious choice is to go with the bigger savings since it makes the most use of my points. However, if you’re looking for the cheapest possible trip, you might want to consider the first option.

Let’s use another example, let’s say you are planning a trip to Lake Tahoe and you are a Hyatt Gold Passport member with a Hyatt credit card from Chase (currently offering 2 free nights if you spend $1,000 in three months). You have your two free nights already, and you’ve added those to the 30,000 points you’ve already accumulated staying at Hyatt hotels throughout the years as part of their Gold Passport membership. If you want to stay at the Hyatt Regency in Lake Tahoe, you would pay $165 a night with their current promotion, which is a snow and play promotion that offers the 4th night free. Instead of paying for five nights, you’re not only paying for 4 at a rate of $165 per night for a grand total of $660 but wait – you have two free nights, too, so you’d actually pay for two nights only for a total of $330. It doesn’t seem as if there is any reason at all to bother with your points here since that rate is so cheap as it is. Do you want to waste 40,000 hard earned points to save $330? Probably not.

However, let’s say you want to take advantage of the ski package, which brings your nightly rate up to $269 per night and eliminates your free night. Now you have to pay $1,345 for the week. You have two free nights, so that drops your rate to $807 total. Now, for 20,000 points, you can stay free of charge for one night. You have 30,000, so you could stay for a third night free bringing your total down to $538 for two nights paid for. Or, you could purchase some Hyatt points (you’d need another 30,000 to get two more free nights and stay free and clear) for a total of $720 – not worth it since the two nights you’d pay for already are only $538.

This leaves us with points and cash. This is a category five hotel, so you’d pay $125 plus 10,000 points per night. That would bring your grand total to 20,000 points used of your 30,000 and $250 out of pocket. It might be worth it to you, or it might not.

Other Hotels

There are a number of great hotels in this area of the country, including Hyatt brands and Hilton brands. Depending on what you want, you can use the same formula we used to calculate the SPG hotels and see what you might get for your buck. Obviously, you want to choose a hotel to which you already reign as a member, but you can apply for a new membership and credit card at the same time and earn bonus points, purchase more points and even use cash and points programs to make the most of planning your winter trip.

It’s almost impossible to tell you how to plan your winter trip using your points since we have no idea how many points you have, where you have them, which companies you have them with, where you live and when you want to travel. However, we use basic formulas to figure out whether or not it is worth it to pay cash, cash and points or with points. You can do the same, but the value of your points for your hotel, airlines and even your ground transportation really does depend on your personal financial situation. What makes a point more valuable might mean more out of pocket, but more in return to me, but it might mean too much out of pocket to you. Use our tips and you will find the best solution for planning your winter trip using your points and miles to the best of your personal financial ability.

Photos by Getty Images


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