Check out this wine caddy. The one pictured holds one bottle of wine with two glasses. When made, I add a small piece of wood that holds the glasses in place until you are ready to remove them. Options include
Type of wood
Size of piece
Amount of wine glasses held in place 2 or 4
Stained or painted
Rustic or modern
Custom lettering / print
Average price is $35, but will very on the details.