The Cherry Tree Inn Bed and Breakfast

Cherry Tree Inn Bed and Breakfast is a characterful Victorian venue and boutique stay in the heart of Woodstock, Illinois, ideal for planners seeking a distinctive backdrop for intimate occasions. Best known as the Groundhog Day house, the property blends film‑famous charm with thoughtful hospitality and versatile spaces for celebrations and gatherings.

For weddings and social events, the team specialises in small affairs, elopements and mini weddings, with simple styling available in the gardens, by the gazebo or indoors. Most events work beautifully with up to around 25 guests, and ceremonies and receptions can be arranged for larger parties by prior agreement, with an absolute maximum of 60. Inside, planners will find a series of elegant rooms that encourage seamless flow, including a grand parlour suited to informal seating, a bistro‑style games room and a formal dining room. Whole‑house rental places all four guest suites at your disposal, each with a private bathroom, creating a convenient stay‑and‑celebrate option for couples, VIPs or corporate groups.

The inn offers curated packages for quick‑turn elopements and intimate receptions, and can connect you to preferred local suppliers for photography, florals, cakes, music, private chefs and planners. Breakfast features locally sourced produce, while offsite catering and private‑chef dining can be integrated for events. The setting is a short walk from Woodstock Square and the Opera House, so photo opportunities and post‑event activities are close at hand. Parking plans are supported for larger guest counts, and respectful sound levels are observed, with lightly amplified music welcomed during daytime and early evening hours. For a warm welcome, distinctive setting and turnkey support, this venue is a smart choice for small weddings, celebrations and retreats.