This post contains references to products from one or more of our advertisers. We may receive compensation when you click on links to those products. For an explanation of our Advertising Policy, visit this page.
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 had easily been several decades since my extended family took a ski vacation together to our collective favorite state of Colorado. We’d tried for years to make it happen, but schedules and finances pegged 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. This year, it finally happened again. Spoiler alert: It was worth the wait.
We 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 to 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.
Now that the trip is in the memory books, I want to walk you through the details.
Don’t Be Scared by the Initial Price Tag
Our three-night stay at a house minutes from Breckenridge rang in at about $3,300 all-in. That sounds bad, but the house has six bedrooms and on paper sleeps up to 22 people. Two of the rooms have creative sleeping arrangements utilizing bunk beds, with the “kid room” featuring an impressive six bunk beds (that were all used). Since there are six bedrooms and five 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 was it less expensive than hotels in terms of lodging, but thanks to the full-kitchen and refrigerator, there was ample opportunity to cook simple meals and save hundreds of dollars over eating out. Think pancakes for dinner, eggs and bacon for breakfast and even a fantastic vegetable stew with cornbread on the final evening.
Frankly, I’m not even sure how a family of 18 with six little kids could have really eaten out even if we tried! (The top-notch ski restaurants will have to wait for next time.)
Making sandwiches to eat on the mountain for lunch was one of our simple but very cost-effective strategies to save money without expending too much effort as each chicken fingers and fries meal on the mountain was $15+ a pop.
Hanging Together Is the Best Part
The heart of the house wasn’t actually the kitchen (though that was a close second), but rather it was the foosball table located just next to the kitchen. This was the epicenter of the action for the little kids … and the “big kids.” Booking a house with a built-in activity like foosball, darts or a pool table is an added bonus for included entertainment. In the summer, an outdoor pool would be great, too (minding very real safety concerns for non-swimmers).
The hot tub, living room with a fireplace and even a (Grandpa Points created) sledding track were all popular hot spots that served as the backdrop for fun and memories when we weren’t skiing at Breckenridge.
Economics aside, renting a large house rather than individual hotels rooms means you have a place to 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 300-square-foot hotel rooms. I’m 100% certain that the “downtime” in the house will ultimately be the strongest lasting memory for this next generation, too.
Find the Right Vacation Rental House
Finding the right vacation house for your family may take some work. Speaking for myself, I’m too old (and grumpy) to bunk up on a couch and share bathrooms with lots of people for very long, 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.
Don’t skimp on the search filters. 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).
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%. In other words, you may have to go with an “If you build it, they will come” mentality. 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.
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.
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.
The biggest issue with our home rental was well-disclosed online. In inclement weather, the house can be very hard to access in part due to a high angle approach to the house on roads that aren’t consistently plowed. In fact, one of our rental cars (not the Audi Silvercar) had to be pushed a bit up an icy hill. Not ideal, but thankfully the other vehicles could handle it.
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.
Consider booking directly. I didn’t do this as I like the protections of booking via a site like VRBO, but you can sometimes save some money by tracking down the owner and booking the property directly.
Buy the insurance. When traveling with lots of different family members, the last thing you want is to argue over who needs to pay for damage should that occur. We paid $79 for an insurance policy offered through VRBO to cover us instead we unintentionally caused some damage to the home.
Here are some additional tips when booking a vacation home rental.
Tips for Sharing the Same Space
If you have booked a large enough home for your group, then not stepping on each other’s toes is much easier to accomplish. After a day or two (or less), some people will need space to retreat to and that’s OK. Most people don’t live with 20 extended family members, so don’t expect 24/7 togetherness either in the home or when you venture out to ski or explore.
If there’s one family outing per day, that gives folks the opportunity to join in the fun or know there will be chunk of time that the house is calmer — enjoying either option is a great choice. I don’t recommend more than one big activity per day as simply getting 20 people out the front door is a process.
I’m probably going to anger the environment a bit with this tip, but using paper plates, cups and paper towels really helps with this many people. Dishes from even a simple meal are pretty significant when dealing with about 20 people, so if there are easy ways to reduce that burden, I vote for taking that route.
Also, pack some card games. Playing Dutch Blitz, poker or even Uno is probably a safer (and more fun) activity than letting the post-dinner conversation veer into politics.
Earn Bonus Points on Home Rental
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 I earned 3 points per dollar on $3,300+ 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 the logistics of a large family vacation is not easy, nor is finding the perfect home rental that fits within everyone’s budget and meets everyone’s needs. While many trips I can book within minutes, this one took a few years to pull together. Even with all that, I honestly didn’t know exactly who all would be able to join for sure until they walked in the door. But, that’s OK. In the end, the family adventure was even better than imagined and most of the “magic,” wouldn’t have happened were it not for staying under the same snowy roof.
Bottom line: Don’t give up on your extended family travel dreams. Keep looking for houses, checking for deals, talking to family members and perhaps one day the stars will align. Now that we have had a taste of how fun it is being together, I can’t wait to dive back into planning another gathering.
Featured image by anyaberkut / Getty Images
Know before you go.
News and deals straight to your inbox every day.
WELCOME OFFER: 60,000 Points Terms Apply.
TPG'S BONUS VALUATION*: $1,200
CARD HIGHLIGHTS: Delta Sky Club and Centurion lounge access, $200 annual airline fee credit and up to $200 in Uber credits annually
*Bonus value is an estimated value calculated by TPG and not the card issuer. View our latest valuations here.
- Earn 60,000 Membership Rewards® points after you use your new Card to make $5,000 in purchases in your first 3 months.
- Enjoy Uber VIP status and free rides in the U.S. up to $15 each month, plus a bonus $20 in December. That can be up to $200 in annual Uber savings.
- 5X Membership Rewards® points on flights booked directly with airlines or with American Express Travel.
- 5X Membership Rewards points on prepaid hotels booked on amextravel.com.
- Enjoy access to the Global Lounge Collection, the only credit card airport lounge access program that includes proprietary lounge locations around the world.
- Receive complimentary benefits with an average total value of $550 with Fine Hotels & Resorts. Learn More.
- $200 Airline Fee Credit, up to $200 per calendar year in baggage fees and more at one qualifying airline.
- Get up to $100 in statement credits annually for purchases at Saks Fifth Avenue on your Platinum Card®. Enrollment required.
- $550 annual fee.
- Terms Apply.
- See Rates & Fees