The Connecticut inn set for this film was reused by Paramount 12 years later as a Vermont inn for the musical White Christmas (1954), also starring Bing Crosby, and again with songs composed by Irving Berlin.
When Irving Berlin won an Oscar for his song "White Christmas" from this movie, he became the first artist to present himself with an Academy Award.
The firecracker dance sequence was added to the movie as a patriotic number, following the attack on Pearl Harbor, which took place during filming. The montage preceding the firecracker dance includes shots of war-time production, military exercises, General MacArthur, and President Roosevelt. The dance number required three days of rehearsal and took two days to film. Fred Astaire did 38 takes of the number before he was satisfied with it. The crew members had to wear goggles during filming, because the sand from the firecrackers flew into their faces. Also, animation was added to make the firecracker "blasts" more dramatic. Later, Astaire's shoes for the dance were auctioned off for $116,000 worth of war bonds.
For the "drunk" dance, Fred Astaire had two drinks of bourbon before the first take and one before each succeeding take. The seventh and last take was used in the film.
The animated Thanksgiving sequence, in which a turkey jumps back and forth on the calendar between the third and fourth Thursday in November, is a topical reference to the "Franksgiving" controversy. Thanksgiving was always on the last Thursday in November, and in 1939 the last Thursday was November 30, the fifth Thursday that month. So in 1939 and 1940, President Franklin D. Roosevelt' attempted to change Thanksgiving to the fourth Thursday in November, instead of the last, in an effort to bolster holiday retail sales by starting the Christmas season earlier. This led to a joint resolution in Congress, which Roosevelt signed into law in 1941, officially designating the fourth Thursday in November as Thanksgiving Day. Holiday Inn was released in 1942, the first Thanksgiving when this change was in effect.