Vacancy Blog

THE CALENDAR FOR PLANNING YOUR TRIPS

Written by Vacancy Blog | Oct 20, 2026, 6:53:47 PM

2027 is almost here, and with it come plenty of perfect dates for traveling. The best way to make the most of them is to keep an eye on them starting now: that way, you can choose your destination at your own pace, book in advance, and be all set for each date.

Winter ☃️

  • Martin Luther King Jr. Day: Monday, January 18 (long weekend from the 16th to the 18th)
  • Presidents’ Day: Monday, February 15 (long weekend from the 13th to the 15th)

Spring 🌷

  • Spring Break: March, depending on the school district
  • Holy Week: March 21–28

Summer ☀️

  • Memorial Day: Monday, May 31 (long weekend from May 29–31)
  • Juneteenth: observed on Friday, June 18 (long weekend from June 18–20)
  • July 4: falls on a Sunday, so it is observed on Monday, July 5 (long weekend from July 3–5)
  • Summer Break: June through August

Fall 🍁

  • Labor Day: Monday, September 6 (long weekend from the 4th to the 6th)
  • Columbus / Indigenous Peoples’ Day: Monday, October 11 (long weekend from the 9th to the 11th)
  • Thanksgiving: Thursday, November 25

New Year’s Eve 🎆

  • Christmas: Saturday, December 25
  • New Year’s Day 2028: Saturday, January 1

A tip for using this calendar
Pick the two or three dates that matter most to you right now and start with those. It’s best to book your peak-season trips first.

Before the year begins, check your membership
To take advantage of each of these dates with Vacancy Rewards, your membership must be active. That way, you can continue booking at member rates and earning points that you can use for reservations on the platform. If your membership is about to expire, now is a good time to renew it so you can start 2027 with everything in order.