Olivia’s Cottage
The ultimate romantic getaway in Maryland awaits in Olivia’s Cottage. Starting at $399 per night.
Luxury Chestertown, MD, Lodging
Lodging at Our Romantic Maryland Bed and Breakfast
The rooms, suites, and cottages at our charming bed and breakfast in Maryland have been appointed with your comfort in mind. All of our Chestertown lodging options are beautifully decorated with their own unique amenities. Every guest will have use of our entire property including our parlor rooms with fireplaces and games to enjoy, the outdoor gardens, and our dining room where you can enjoy a homemade breakfast and afternoon tea.
The exceptionally grand and spacious rooms and suites in the 1860 Manor House offer you a glimpse into the past with the privacy you expect at a romantic B&B in Maryland. The cottages are located away from the Main House nestled in the woods giving you a more secluded lodging option for your Eastern Shore getaway. Enjoy luxurious amenities ranging from wood-burning fireplaces to pet-friendly accommodations. Please, read about our wood-burning fireplace policy here.
View all of our accommodations below to start planning your romantic getaway to Maryland’s Eastern Shore!
Mulberry Cottage
The Mulberry Cottage is utterly private providing an ultimate romantic getaway in MD. Starting at $399 per night.
Sunset in the Garden Cottage
This cottage room with a private entrance is located in the Garden Cottage. Starting at $299 per night.
Sunrise in the Garden Cottage
This cottage room is located in the Garden Cottage with a private entrance that offers views of the garden and lawn and is a guest favorite. Starting at $299 per night.
Russell’s Cottage, our ADA accommodation
Beautiful, private cottage located in an 1860 smokehouse features high ceilings with exposed wood beams. Starting at $259 per night.
The Apartment
The newest accommodation at our Chestertown Bed and Breakfast is a chic, contemporary one bedroom flat. Starting at $259 per night, for two.
Fairy Hill Suite
A path leads past the old well to this charming two-level suite at our romantic inn in Maryland, which has the feel of a colonial farmhouse. Starting at $259 per night.
Sophie’s Suite
The two-room suite with creamy hues features a window-lined sitting room with club chairs, desk, and TV with DVD player. Starting at $259 per night.
Blue Room
Bright, floral and spacious 2nd floor room features huge windows with front and side lawn views at our Chestertown Inn. Starting at $239 per night.
Yellow Room
Bright, grand and spacious, 2nd floor room that features huge walnut windows with views of the garden. Starting at $239 per night.
Red Room
The Red Room is a spacious room on the third floor with large windows on three sides and a view of the surrounding landscape. Starting at $239 per night.
Green Room
This spacious third floor room at our romantic bed and breakfast in Maryland, has many windows, all with treetop views. Starting at $229 per night.
Simone’s Retreat
This bright and elegant second floor hideaway is located in the oldest part of the house. Starting at $199 per night.