Usually means: Festive period of celebrations, gatherings.
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We found 17 dictionaries that define the word holiday season:

General (14 matching dictionaries)
  1. holiday season, the holiday season: Merriam-Webster.com
  2. holiday season: Oxford Learner's Dictionaries
  3. holiday season: Vocabulary.com
  4. holiday-season: Wordnik
  5. the holiday season: Cambridge Advanced Learner's Dictionary
  6. holiday season: Wiktionary
  7. holiday season: Dictionary.com
  8. Holiday season: Wikipedia, the Free Encyclopedia
  9. holiday season: Rhymezone
  10. holiday season: Free Dictionary
  11. holiday season: Mnemonic Dictionary
  12. holiday season: Dictionary/thesaurus

Business (2 matching dictionaries)
  1. holiday season: Legal dictionary
  2. holiday season: Financial dictionary

Computing (1 matching dictionary)
  1. holiday season: Encyclopedia

(Note: See holiday_seasons as well.)

Definitions from Wiktionary (holiday season)

noun:  (US, Canada) The period of the late fall and early winter when several holidays occur, such as Halloween, American Thanksgiving, Christmas, New Year's Day, Hanukkah, and Kwanzaa
noun:  (British English) A period in the summer when people go on holiday (vacation).

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