Planning for ski season: How I booked a $1,500 vacation rental for just 45,000 points

Being a ski bum on the East Coast is no easy feat.

To get some good vertical every year requires being strategic about booking ski trips — especially for those popular three-day holiday weekends. With the ever-rising costs of lift tickets, flights, lodging, rental cars and sometimes ski rentals, one quick weekend can easily turn into a multi-thousand dollar adventure.

That’s why it is so important to plan ahead for complicated trips. After all, the best time to buy your lift tickets is before the previous winter has even ended. We bought our ski passes back in April.

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Points and miles help to reduce costs, though there is only so much one can do, especially with a big group. Often you can book airfare with miles, but the available hotel rooms may not fit your group’s needs. If you need to sleep four to six people, you need to get creative — unless you’re willing to shell out a ton of points on multiple hotel rooms.

With that in mind, I decided to book a rental home for this year’s big ski trip. In addition to more space, having a kitchen to cook your meals and separate bedrooms can make a big difference when traveling with a group.

Let’s take a look at how I redeemed just 45,000 Wyndham Rewards points for a three-night vacation rental near the slopes.

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Book a Vacasa Home with Wyndham Rewards

With Wyndham and Vacasa’s partnership, Wyndham members can book rental properties for 15,000 Wyndham points per night per bedroom. While a studio or a one-bedroom would cost 15,000 points, a three-bedroom would cost triple that.

A terrific advantage of booking Vacasa rentals through Wyndham is that it waives all fees (normally, you’ll get hit with a pricey cleaning fee, anywhere from $100 to $200 per stay). Additionally, all other property and rental fees are waived — meaning that there is also no sales tax on most bookings.

While this is an amazing deal, there are drawbacks: blackout dates and minimum stay requirements. On top of that, blackout nights are not shown online; you can only learn what those are by calling. The minimum stay requirements are generally shown on the Vacasa listing.

In my personal experience (and noted on Frequent Miller), I have found that properties listed for over $350 per bedroom per night, before taxes and fees, generally are blacked out and not available to book via this method. However, this is not a hard-set or published rule.

Related: The ultimate guide to earning and redeeming Wyndham Rewards

Searching for the property


Booking a vacation rental on points has its pros and cons. One is that while there are often more options available than hotels, each property only holds one group at a time, making availability harder to find.

For the trip in question, I wanted anything within walking (or shuttle) distance to Keystone Resort, although I would have settled for anything within driving distance.


I started by going to and entering my travel dates for Keystone, Colorado. Additionally, I wanted to keep it at a cost of 15,000 Wyndham points per night, so I filtered my search to one bedrooms (studios are listed as 0 bedrooms, which would have been too tight for my family) and a maximum price of $350 per night.


Quite a few options appeared. I zoomed in on the map to find walkable/shuttle distances to Keystone and used the “Search Here” feature to limit the area. At that point, I had what I suspected were properties bookable on points.

Diving deeper into each property, I looked for properties that had a loft or basement that served as another sleeping space without counting as a two-bedroom property (which would have pushed me to 30,000 points per night).


After taking time to comb through each property, I made a list of my top three choices and called Wyndham to book my Vacasa stay. It has a special number for Vacasa bookings: 866-996-7937.

Related: 7 ways to make your next ski trip better than the last

Transferring Capital One miles to WyndhamI

The booking process was surprisingly simple.

I called Wyndham and the agent was able to confirm that my property of choice was eligible for an award booking.

There was just one issue: I didn’t have any Wyndham Rewards points in my account yet. I turned to my Capital One Rewards account and transferred 45,000 miles to Wyndham for a three-night stay. The agent couldn’t hold award space before I transferred the miles, but was happy to wait on the phone during the process. The miles posted to my Wyndham Rewards account almost instantly.


The agent was then able to complete the booking over the phone and told me to expect a confirmation email within 24 hours. Sure enough, I got a confirmation email from Wyndham thanking me for my redemption and one from Vacasa with further instructions on the property.


Evaluating my redemption

While the property was just below $350 a night in cash, factoring in the taxes and fees would have brought my three-night stay in Colorado to $1,472.87.

To book an almost $1,500 per night stay for 45,000 points is good for any program. In the end, I redeemed my Capital One miles for 3.3 cents per point. That’s well over TPG’s valuation of 1.85 cents apiece.


Bottom line

Ever since getting the Capital One Venture X Rewards Credit Card, I have wanted to try using some of my Capital One miles through Wyndham Rewards for vacation rentals. I am happy I did.

Booking these rentals can pose significant value, especially in markets with limited hotel options.

Making a ski vacation happen on points and miles is not always easy, but it is well worth it when you can finally zoom down a mountain for the day — then relax by a fire with a cup of hot chocolate in your hands made in your own rental’s kitchen.

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