Hotels near Wooster Square are always on sale with CheapOair! Wooster Square is a beautiful neighborhood and a prominent tourist attraction situated in New Haven, Connecticut. Considered one of the best places to taste Italian-American cuisine, Wooster Square is certainly a paradise for food lovers. Wooster Square is also home to many historical attractions making it the perfect place to experience the blend of history, beauty and delicious cuisines. The attraction is particularly famous for hosting the Cherry Blossom Festival which attracts thousands of visitors every day. Find great deals on cheap hotels near Wooster Square and count on CheapOair for all of your travel booking needs!