Holiday Vacations & Celebrations
  • Fireworks over New York City
  • Festive Christmas lights on piñata and building in mexico
  • Couple with santa hats on Caribbean beach
  • Ice skaters at night in European Christmas Market

Holiday Season Vacations & Celebrations

This year, start a new tradition – mark a special occasion with vacation to remember. Celebrate an enduring romance, mark a milestone birthday, honor a special person, welcome new beginnings, or immerse yourself in a new culture. Travel is a great way to connect with family and friends, embrace unique experiences and create holiday vacation memories to last all year round.
  • New Year's Fireworks in Las Vegas

    USA Holiday Vacations

    Ring in the new year in Las Vegas; trade in a traditional Thanksgiving with theme park thrills; spend winter break on the slopes or with a warm drink enjoying the sparkling beauty of a mountain resort. The possibilities are endless.
    USA Vacations
    Ring in the new year in Las Vegas; trade in a traditional Thanksgiving with theme park thrills; spend winter break on the slopes or with a warm drink enjoying the sparkling beauty of a mountain resort. The possibilities are endless.
    USA Vacations
  • Festive holiday flags on Mexican church

    Mexico Holiday Season

    The holiday season in Mexico means three weeks of festivals, religious events and traditional foods to enjoy. Combine it with balmy winter weather for the perfect family getaway.
    Mexico Vacations
    The holiday season in Mexico means three weeks of festivals, religious events and traditional foods to enjoy. Combine it with balmy winter weather for the perfect family getaway.
    Mexico Vacations
  • Maui Beach at Sunset

    Hawaii Holiday Season

    Experience the joy and festivities of the holiday season, and save on vacations to Oahu, Maui and Kauai with exclusive offers only available through Pleasant Holidays.
    Hawaii Vacations
    Experience the joy and festivities of the holiday season, and save on vacations to Oahu, Maui and Kauai with exclusive offers only available through Pleasant Holidays.
    Hawaii Vacations
  • Woman in Santa hat on Caribbean beach

    Christmas in the Caribbean

    Celebrate the old and welcome in the new in the Caribbean, with street parties that stretch into the night and unique foods and gifts available at no other time of year.
    Caribbean Vacations
    Celebrate the old and welcome in the new in the Caribbean, with street parties that stretch into the night and unique foods and gifts available at no other time of year.
    Caribbean Vacations
  • Edinburgh Christmas Market at night

    Europe Christmas Markets

    Glittering lights, mulled wine and good company - Europe's holiday markets draw locals and visitors alike for shopping, sightseeing and a warming festival atmosphere. What's more, travel to Europe in the winter means better deals and fewer crowds than during the peak summer months, making this an experience you won't want to miss.
    Europe Vacations
    Glittering lights, mulled wine and good company - Europe's holiday markets draw locals and visitors alike for shopping, sightseeing and a warming festival atmosphere. What's more, travel to Europe in the winter means better deals and fewer crowds than during the peak summer months, making this an experience you won't want to miss.
    Europe Vacations