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Growing up, our extended family would occasionally take big family vacations to the snowy Rocky Mountains of Colorado. I have very fond memories of playing in the snow with my parents, suffering through ski school with my cousins and eventually sailing down the mountain on skis together. To make this happen, our parents would pile us in the back seat of our Honda Accord, drive all night from East Texas to Colorado and we’d all bunk up in a shared condo rental (or at least, that’s how I remember it). It didn’t hurt that skiing was more affordable a couple of decades ago than it is at some of the mega-resorts these days, but I’m sure it still took a lot for our parents and grandparents to pull off these family trips.

But, as the kids and grandparents got older, schedules got tighter and expenses got bigger, these trips unintentionally and unceremoniously ended. It’s now easily been several decades since my extended family took a ski vacation together to our collective favorite state of Colorado. I’ve tried for years to make it happen, but schedules and finances peg it as an especially tall order. But, I’m a bit of a bulldog when it comes to family travel dreams — I don’t let them die easily.

Image by Getty Images / Imgorthand
Image by Getty Images / Imgorthand

This year, we tried again, and found success not with hotel points, but via a massive 22-person, 4,000-square-foot rental house found on VRBO. Believe it or not, we didn’t have wait for one of us to win the lottery to pull this trip off as the math is (shockingly) good, even during the holiday ski season. (I’m not going to link to the exact house yet, but promise to share it after our trip is over.)

I want to share the booking side of the story now as it is shaping up to be a good snow year for Colorado with multiple resorts open early thanks to great early season snow. In fact, Keystone and Breckenridge opened ahead of schedule yesterday, joining destinations such as Wolf Creek, Loveland and A-Basin that have already been open for a few weeks.

Don’t Be Scared by the Initial Price Tag

Our three-night stay near a major Colorado ski resort is scheduled for early January 2019, and rang in at about $3,300 all-in. That sounds bad, but hang with me. The house has six bedrooms and sleeps up to 22 people as two of the rooms have creative sleeping arrangements utilizing bunk beds. Since there are six bedrooms (and almost as many bathrooms), we’ll use the easy math of six families sharing the space, though that number could obviously vary a bit.

Split six ways, the 4,000-square-foot ski house comes out to $183 per family, per night. A quick look at our travel dates on Hotels.com showed that nearby Residence Inn and Wyndham midrange properties are pricing at close to $400 per night, with many hotel options going for more than that. The absolute cheapest property available in the ski resort area came to $261 all-in per night for those same dates.

In that regard, renting a huge fancy house wasn’t just comparable to booking a standard run-of-the-mill hotel room, it was significantly cheaper if you looked at it on a per-family basis. Not only is it less expensive, but we get to use the foosball table, two hot tubs and make use of the large kitchen — none of which we would have to ourselves at a hotel. This means we will probably save money not only on lodging, but on food costs over eating out every meal at ski resort prices (though I’m sure we will sneak in a good meal).

More importantly, we have a place where we can all gather and hang out together in the evenings. As a kid, my favorite part of family vacations was time with cousins just chatting and playing, which is infinitely easier in a house rental than in multiple separate hotel rooms.

GMVozd / Getty Images
GMVozd / Getty Images

Finding The Right Vacation Rental House

While I am very much looking forward to a large family ski trip, I’m not a great sharer when it comes to accommodations. I’m too old to bunk up on a couch and share bathrooms with lots of people, and I think most of my family members feel the same way. This means the majority of the bedrooms at a vacation rental house need to have their own private bathrooms for harmonious family trips. While your needs may be different from ours, find out the wants and must-haves of your group and don’t get tempted to stray from that list. For us, this meant going through many “no’s” before finding the right property, but it can be done, even if you have a large group and a limited travel window.

To encourage you to keep looking for the right spot to create memories on your own big family (or friend) vacation, here are some tips.

  1. Don’t skimp on the search filers. If you need a house with six bedrooms, you need a house with six bedrooms. Don’t waste time looking at houses that are just below what you need. On the same token, don’t look at houses way outside of your price range. Trust me, just don’t go there (until someone in the family does indeed win the lottery).
  2. Get an accurate head count, but don’t wait for every star to align. If you want to take an extended family vacation, at some point, you may have to push the booking button even if some members of the group aren’t yet 100%. Obviously, don’t get yourself in over your head, but read the cancellation policies of the homes and when you get “enough” firm yeses, go for it. You can often cancel until a certain number of weeks or months before travel if it just didn’t all work out. Assuming you have done your best to work out schedules, I also recommend going forward even if some people can’t make it. Some family fun is better than none and there’s always next time.
  3. Shorter trips > longer trips. It is hard for multiple family members to all have the ability to take off a full week at the same time. It is also hard to evenly share the cost of a house if some family members want to be there for a full week and others may only have a long weekend available, so start with a shorter trip. In our case, we booked a big house for three nights, but some people are going to stay at hotels (using points at the Hyatt Place Keystone) before or after the portion of the trip in the house to create their own longer vacation.
  4. Scrutinize reviews, photos and search the internet. This is largely common sense, but when deciding on a vacation home rental, be ruthless in scrutinizing reviews, the provided photos and then do a broader online search to try to find information about the property and owners on another site. Many homes are available on a couple of different sites, so do your homework and look at every available piece of information before deciding this is the one for you.
  5. Look at the pricing calendars. We scored the price we did on the house, in part, because our three nights were the only three left between two longer rentals. Judging by the prices of some other nights, it seems that our nights were discounted a bit because they were a limited availability slot. I’ve also seen large home rental discounts available at the last minute and huge pricing variations if you can go just before or just after true peak season dates, such as the week of Christmas for a ski house rental.

Here are some additional tips when booking a vacation home rental.

Bottom Line

Since this is The Points Guy, I also want to note that our vacation home rental booked through VRBO did code as travel on my Chase Sapphire Reserve. This means 3 points per dollar on $3,000+ charged. However, not everyone who books a home via VRBO is as lucky as we were since the charges do not always code as travel. This is seemingly dependent on whether the owner you rent from is an individual, as is the case for us, or is a property management company.

Planning a large family vacation is not easy, nor is finding the perfect home rental that fits within everyone’s budget. It took a few years for us to get this trip lined up, and it is always possible that life will happen and in January I’ll be telling the story of how my family of four ended up in a house for 22 by ourselves. But hopefully, this is it, and the gorgeous rental house for 22 people that was available for less than the cost of area hotel rooms will be the base for a new generation of family ski memories.

Featured image by anyaberkut / Getty Images

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