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In June, 1906, in the town of Danville, Connecticut, the Miller family—father Nat, mother Essie, sons Arthur, Richard and Tommy, daughter Mildred, Uncle Sid and cousin Lily—prepare for Richard's high school graduation.  Uncle Sid is about to leave for a new position as a reporter on the Waterbury newspaper and, when he proposes to Lily once again, she agrees to marry him, on condition that he stop drinking.

Meanwhile, Richard, who is attending Yale in the fall, tries to kiss his sweetheart, Muriel McComber, and practices his fiery, anti-capitalist valedictory speech.  At graduation, newspaper owner Nat lets Richard recite only the first, inoffensive part of his speech before cutting him off.  When Nat then offers his son a chance to drive the Stanley Steamer home, asking if his conscience will let him enjoy a consumer good purchased off the sweat of the workers, Richard gladly forgoes his Marxist philosophies.

By the Fourth of July, however, some of the Millers have grown concerned that Richard is spending too much time reading his radical books.  Although Essie is aghast, Nat supports Richard, knowing that he is merely going through a rebellious phase.  As everyone makes their picnic plans, Uncle Sid reappears; when Nat realizes that his brother-in-law has been fired, he pretends to suddenly need to re-hire him.

Lily is overjoyed at Sid's return and, thinking he is now sober, wants him to propose again.  At the town picnic that day, however, Sid wins the drinking contest and comes home inebriated.

Meanwhile, Muriel's father, Dave McComber, visits Nat and accuses Richard of trying to corrupt his daughter with kisses and radical love letters.  When McComber says that he refuses to let Muriel see Richard anymore, Nat throws him out, ignoring McComber's threats to pull his advertising from Nat's newspaper.  Nat then confronts Richard, who calms his father by proclaiming his chaste love for Muriel.  Nat gives Richard the letter McComber forced Muriel to write, which causes a distraught Richard to swear revenge.

That night, Sid's drunken antics make everyone laugh except Lily, who cries.  A still angry Richard storms out of the house and meets a college sophomore, who asks him to go out with him and two chorus girls.  After Richard agrees, his worldy wise date, Belle, takes him to a bar and gets him drunk, then leaves him when he tries to reform her.  When she tells the bartender who Richard's father is, the bartender fears he will lose his job, and so throws her out.  She then seeks revenge by writing a letter to Nat informing him where Richard was, while at the same time Richard staggers home and is punished by his parents.

The next day, Muriel asks Richard to meet her in secret, and they profess their undying love and kiss.  When Richard comes home, his parents approve of his love-struck manner, though Nat is concerned about Belle's letter.  As he haltingly attempts to talk to Richard about "the birds and the bees," Richard assures him that he only wants to be with Muriel, a good girl.  Later that night, as Sid and Lily sit together on the porch swing, Richard waves across the street to Muriel, and Nat and Essie watch over everyone, reminiscing about their own love story.

Notes
The working title of this film was Ah, Wilderness.  The film is a musical version of Eugene O'Neill's play Ah, Wilderness!" and the 1935 MGM (nonmusical) film version of his play, which was written by Frances Goodrich and Albert Hackett. Goodrich and Hackett, who were credited with the screenplay of the 1948 film, wrote only the screenplay of the 1935 version.  The title of O'Neill's play was derived from a line in the poem "The Rubáiyát of Omar Khayyám."

A January 1946 HR news item notes that June Allyson and Ray McDonald were set to star in the film. Although Summer Holiday did not mark the motion picture debut of actress Anne Francis, it marked her first onscreen credit, which listed her as "Ann Francis."  Francis' debut was in the 1947 MGM production This Time for Keeps.  HR production charts indicate that Charles Schoenbaum replaced Charles Rosher as the director of photography approximately two weeks after the film went into production.  Although a news item in HR on July 10, 1946 indicated that film editor Albert Akst was being replaced by George White, Akst remained on the film.

Some filming took place at Irvine Park and Busch Gardens near Pasadena, California.  According to a February 1948 DV news item, the final cost of the film was approximately $2,000,000.  Modern sources note that production on the film was hampered by a two-week motion picture industry strike that began on June 22, 1946.  During the strike, Mamoulian suspended full production on the film and used the time to rehearse scenes and pre-record musical numbers.

Although the film was completed in mid-October 1946, it was not released until May 1948.  Modern sources note that the film's release was held up due to MGM's concerns that it would not do well at the box office.  The picture lost nearly $1,500,000 in its initial release.

O'Neill's play was first produced by The Theatre Guild in New York in 1933 with George M. Cohan playing "Nat Miller."  The role was subsequently played by Will Rogers and Harry Carey, Sr.  In addition to the 1935 film version of O'Neill's play, which was directed by Clarence Brown and starred Wallace Beery, Lionel Barrymore, Aline MacMahon and Mickey Rooney, as "Tommy Miller," the play was presented in several television broadcasts, including a Celanese Theatre production, televised on ABC on October 3, 1951, which was directed by Alex Segal and starred Thomas Mitchell and Roddy McDowall; a Front Row Center production, televised on CBS on June 5, 1951, which was directed by Fletcher Markle and starred Leon Ames and Bobby Driscoll; and a Theatre in America Production, televised on PBS on October 13, 1976, which was directed by Arvin Brown and starred William Swetland and Richard Backus.

Music includes:  "Our Home Town," "Afraid to Fall in Love," "Dan-Dan-Danville High," "The Stanley Steamer," "Independence Day," "While the Men Are All Drinking," "You're Next," "Weary Blues" and "The Sweetest Kid I Ever Met," music by Harry Warren, lyrics by Ralph Blane.  A biography of producer Arthur Freed credits Robert Tucker and Ralph Blane with the vocal arrangements, and notes that the song "Wish I Had a Braver Heart," sung by Gloria De Haven, was cut from the film before its release.  Also cut from the picture was the first rendition of Walter Huston singing "Spring Isn't Everything."