Holiday Vacations

Trade in dreary skies and chilly weather for tropical fun in the sun this holiday season! Celebrate the festive season in paradise this year at popular resorts across the Caribbean, Mexico and Central America with something for every travel style. Feel the stresses of the holidays back home fade away as you soak up the sun poolside or enjoy a memorable meal with your family (without having to worry about the dishes afterwards). Book now to reserve your preferred resort and celebrate the holidays in the tropics!

Cayo Santa Maria, Cuba
Save up to 32%!
Windsor to Cayo Santa Maria
Tue, January 5, 2021 7 days All inclusive
Reg. $1,455
From $995 taxes and fees incl.
Prefer another date?
Save up to 16%!
Windsor to Varadero
Thu, January 7, 2021 7 days All inclusive
Reg. $1,895
From $1,585 taxes and fees incl.
Prefer another date?
Save up to 24%!
Windsor to Riviera Maya
Mon, January 4, 2021 7 days All inclusive
Reg. $2,205
From $1,675 taxes and fees incl.
Prefer another date?
Save up to 37%!
Windsor to Jamaica
Sun, January 3, 2021 7 days All inclusive
Reg. $2,945
From $1,845 taxes and fees incl.
Prefer another date?