Top Chestertown Venues

Brampton Inn’s elegant 1860 Manor House, terrace and landscaped gardens is a perfectly suited intimate wedding venue in Maryland. Whether you you’re looking for a romantic destination wedding, eloping or plan to renew your vows, creating a memorable and romantic setting for your special day on Maryland’s Eastern Shore is what we do best! Our beautiful country estate offers several locations to host your celebration. We have several packages to choose from ranging from just the wedding couple to 125 guests and we would love to help you make your day absolutely perfect!

• Spaces for 275-300 Guests
• 1 Outdoor
• 1 Historic Space
• 1 space at this venue

Stepne Manor is a beautifully restored Colonial Revival estate in the heart of historic Chestertown, Maryland, originally built in 1690. With stately columns, a wide covered front porch, and elegant brick pathways leading across an expansive lawn, the property sits just steps from downtown Chestertown's galleries, shops, and waterfront — offering both the character of a historic home and the ease of a walkable small-town setting. The manor accommodates events of up to 275 guests on its grounds, with designated areas for ceremonies, cocktail hours, and receptions across the front porch, side yard, magnolia tree area, and front circle. Exclusive use of the property is included with every rental, along with a three-day, two-night stay sleeping up to 15 overnight guests across five bedrooms. Couples and clients are free to bring their own caterers, bar staff, and vendors — giving full flexibility to shape the event entirely.

• Spaces for 50-400 Guests
• 1 Historic Space
• 1 Estate
• 1 Mansion

Brittland Manor is a historic hilltop estate along the Chester River in Chestertown, Maryland, offering exclusive access to more than 500 acres of Eastern Shore countryside for weddings, retreats, and private celebrations. The Georgian-style manor house sits above sweeping river views, with curated gardens, a poolside entertaining area, a waterfront dock, and open lawns that together create a range of settings for every part of a wedding weekend. The estate operates as a private retreat rather than a single-event venue, centering its wedding experience on a three-day, two-night stay that gives couples and their guests full run of the grounds. Outdoor events accommodate up to 400 guests on the brick patio and under sailcloth tent structures, while the manor house itself is suited for smaller indoor gatherings of up to 50. On-site accommodations across the manor and the adjoining River Lodge sleep up to 41 guests across 15 bedrooms, keeping the wedding party together from rehearsal dinner through farewell brunch. Brittland Manor has been featured in Brides, Style Me Pretty, Washington Bride & Groom, Magnolia Rouge, and Premier Bride.

• Spaces for 100-250 Guests
• 1 Outdoor
• 1 Historic Space
• 1 Estate

The Inn at Mitchell House is an 18th-century manor home set on 12 acres between Chestertown and Rock Hall on Maryland's Eastern Shore, less than half a mile from the Chesapeake Bay. Built in stages beginning in 1808, the property has been operating as a bed-and-breakfast inn since the early 1980s and offers a historic, pastoral setting for small gatherings and outdoor celebrations. The inn's sweeping lawn overlooks Stoneybrook pond, with wooded fields and open grounds well suited to outdoor ceremonies and receptions. The venue accommodates up to 100 guests for weddings and private events, with the option to host additional guests beyond that threshold. Couples booking the venue have full use of the main inn — with its six named guest rooms, parlors, dining room, and screened porch — along with the Stone's Throw Cottage, a private one-bedroom rental with a great room, gas fireplace, and its own deck. The inn has earned coverage in The Washingtonian, The New York Times, and Baltimore Magazine, and received the 2022 WeddingRule Editor's Choice Award.

• Spaces for 300 Guests