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 romantic bed and breakfast in Maryland have been appointed with your comfort in mind. All of our Chestertown, MD, 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. If you’re looking for elegant lodging in Chestertown, MD, that feels like home, Brampton Inn is the perfect place to stay.
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 bed and breakfast in Maryland. Each of our Chestertown, MD, accommodations has an en-suite bathroom with a shower or spa tub and a king or queen bed. You can enjoy wood or gas-burning fireplaces during the winter months while you cozy up in your spacious living area.
The cottages are located away from the Main House nestled in the woods giving you a more secluded lodging option for your Chestertown getaway. Each cottage features wood-burning fireplaces during the colder months (used November 15 through March 31) and a private bathroom with a whirlpool tub, deep soaking tub, infinity bath or jetted showers, and privacy. You’ll also find different amenities unique to each of our Chestertown lodging options such as full kitchens, private porches and breakfast in bed options. The Apartment in the Woods and Russell’s Cottage are our pet-friendly Chestertown, MD, lodging options with outdoor areas to accommodate both you and your dog.
Please, read about our wood-burning fireplace policy here.
View all of the lodging options at our romantic bed and breakfast in Maryland below to start planning your romantic getaway to Maryland’s Eastern Shore.
The Mulberry Cottage is utterly private providing an ultimate romantic getaway in MD. Starting at $399 per night.
This cottage room with a private entrance is located in the Garden Cottage. Starting at $299 per night.
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.
Beautiful, private cottage located in an 1860 smokehouse features high ceilings with exposed wood beams. Starting at $259 per night.
The newest accommodation at our Chestertown Bed and Breakfast is a chic, contemporary one bedroom flat. Starting at $259 per night, for two.
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.
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.
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.
Bright, grand and spacious, 2nd floor room that features huge walnut windows with views of the garden. Starting at $239 per night.
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.
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.
This bright and elegant second floor hideaway is located in the oldest part of the house. Starting at $199 per night.