Holiday Hill is located in the central Connecticut countryside, on the Cheshire/Prospect town line . This beautiful 200-acre resort has been providing first-class food, service, facilities and entertainment to groups of many sizes for over 50 years. We'd love to welcome your group for a day of fun and relaxation. From early May through September we host a large range of group events including company picnics, student trips and family events of up to 5,000 guests.