2020 Holiday Vacation: Your Ultimate Booking Guide



If you have anything in common with most other Americans right now, you’re feeling the bite of the travel bug and the resulting insatiable wander-itch. We at Cascara have seen this first-hand: We’ve been booked solid ever since the green light was given for overnight stays in our gorgeous little town of Sunriver, Oregon. In fact, the Washington Post recently wrote an article labeling the phenomenon of “revenge travel,” a resurgence of visitors suffering from a COVID-restriction hangover. While the virus is still prevalent in many areas and precautions must be taken, experts are already seeing a bounce back for resort destinations within driving distance of major cities. That includes Cascara! 

So, what does all that mean for you and your holiday booking plans? “If you want to book a property with everything on your wish list for the upcoming holiday season, you’ll want to book now,” say Cascara owners Greg and Stacy. In fact, if traveling for the holiday season is new to you and your family, you might be surprised to discover that most holiday bookings are done months in advance, before the season even begins. Because of that and the revenge travel trend, Cascara is poised to have one of its biggest holiday seasons to date. 

Stay ahead of the competition, and plan your family dream vacation with the following tips from Cascara’s booking team.

Step 1: Get Family Members on Board

We know that many of you have developed fun, think-outside-the-box traditions for the holidays, but most of our guests still enjoy booking their vacation with their extended families. That usually means booking larger multi-family homes that can accommodate a crowd. The first thing that you’ll want to do is recruit extended family members, write down their bedding preferences, and get on the same page about your combined budget. If there are any amenities that are completely non-negotiable to certain family members, now is the time to establish those. Here are typical non-negotiable amenities that guests ask for: 
  • Location, location, location: proximity to popular destinations
  • Hot tub onsite or in home
  • In-home laundry
  • Entertainment technology
  • Well-appointed kitchen
  • Access for disabled family members

Step 2: Book Your Property

Begin by browsing online. Of course, we recommend starting at our website, CascaraVacations.com. However, booking online can be a bit overwhelming, no matter how well the site is built. This is especially true if your list of requirements has grown a bit long. You may have an easier time speaking with a reservationist. Many of them know the properties like the backs of their hands and can set your expectations appropriately. 
Here are a few things to expect when you do finally decide to start the booking process: 
  • Expect higher prices. Demand is highest during the holiday season, so the market price for rentals rises to meet demands. Plan for a little higher budget. 
  • Competition is stiffer. You may want to lower your non-negotiable list for larger properties, as the most ideal homes are booked up to one year in advance. 
  • If you’re flying, book your flights the same day. If you’re flying, do not wait to book your flights separately. Check to make sure there is a flight available for the dates that you want to book, and book that flight immediately following your reservation. In the reservation world, we’ve often had guests who need to move or cancel their trip altogether because they did not plan their flights appropriately. 
  • If possible, book a rental car with 4WD. If you’re flying and need to rent a vehicle, request 4WD. Don’t let that snow catch you by surprise!

Step 3: Plan Your Major Activities

As the family member who has been appointed intrepid trip planner, you may think that your job is done. But wait, there’s more! You’ll also want to plan your major activities well in advance. While this tip normally rings true all the time, COVID restrictions have limited capacities at most businesses. If you’re planning on a couple nice evenings out with the entire family, you’ll need to call well in advance to request reservations for the holidays. We recommend calling as early as November to ask when restaurants are taking those reservations. If they’re not taking bookings yet, mark the day that they begin with a reminder on your calendar.

Step 4: Start Your Packing List 

Finally, plan your outdoor and at-home activities. Take into account entertainment for the children, such as books, devices, games, etc., as well as for the adults (poker, anyone?). If you’re planning on preparing at least some meals at the vacation home, speak with the front desk to make sure all the kitchen supplies you need will be sufficiently stocked.



Step 5: Now, Chill Out

If you’ve followed all the steps we’ve laid out for you, chances are that you’re going to have a great holiday vacation. However, even the best-laid plans can hit snags. Remember that as you’re traveling, checking in, and going about your vacation, you’re there to have a good time, create memorable experiences, and bond with your family. The rest is all just details.