The Brampton Bed and Breakfast Inn in Chestertown, Maryland is a romantic oasis perfect for private getaways and honeymoon accommodation and is a meticulously restored 1860 National Register manor house. This award winning bed and breakfast offers the grace and charm of a 19th century country estate, where you can leave the world outside the door, and simply relax in beautifully appointed guest rooms, that are comfortable with modern amenities, and there are secluded cottages available many with whirlpool tubs or spa showers, and all with unparalleled privacy. Freshly prepared a la carte breakfasts are served in the morning, and afternoon tea and refreshments await. The Brampton Bed and Breakfast Inn is also a dream Maryland wedding venue and perfect setting for your special day.READ MORE

Widow's Walk Inn B&B is located in the historic district of Chestertown, Maryland, and is close to many historic sites, quaint gift shops, and fine restaurants. A stay at the Widow's Walk Inn B&B takes you back down memory lane to how things used to be, here you will find quiet tranquility, a soothing of the soul, and a lovely welcoming home with air conditioned rooms and ceiling fans. Enjoy antique furnishings and family treasures, relax on the rocking chairs or swing on the front porch, and simply enjoy.READ MORE

The Bookplate in Chestertown, Maryland offers a wide array of books in a broad array of categories, and they emphasize the history of Chesapeake Bay with many books relating to the history, historical sites, colonial and revolutionary heritage of Maryland's Eastern Shore. The Bookplate is a wonderful place to visit and has an expanded section on maritime history, exploration, sailing, navigation, nautical fiction and tales of the sea, as well as the fields of art, architecture, design and so much more, here there is something for everyone's historical interest and taste.READ MORE

Stepne Manor circa 1690 in Chestertown, MD offers a wonderful stay on a historic site and landmark in a manor house with wide covered porch. This stunning town manor house can comfortably sleep up to fifteen guests and has a large kitchen with dining table. Interior rooms are fully furnished and showcase unique architectural designs. Stepne Manor is within walking distance to downtown Chestertown, and is also the perfect venue for meetings and wedding ceremonies.READ MORE

Sophisticated Vintage in High Street, Chestertown, Maryland are purveyors of stylish finds, including vintage furnishings and accessories, contemporary decor, eclectic jewelry and so much more. Come view antique furnishings, artifacts and collectibles in wonderful surrounds, immerse yourself in a time gone by inside this peaceful oasis, and a really fun place to visit. Come shopping for gifts, a little something special for yourself, at Sophisticated Vintage everyone's taste is catered to, and pieces of timeless elegance and charming vintage await.READ MORE

Massoni Art in Chestertown, Maryland offers contemporary fine art, paintings, sculpture, photography and prints, and is the perfect place for that corporate gift. Enjoy wonderful exhibitions by gallery artists and visiting artists as well as a very strong on-line presence. Massoni Art brings art to the workplace and has worked in collaboration with architects, developers, interior design firms, art consultants, and non-profit organizations and more.READ MORE

The Fish Whistle is a waterfront restaurant in Chestertown, Maryland overlooking the Chester River, and here it's all about the food, with excellent nightly specials. Enjoy exquisite American cuisine of burgers and wings, oysters and prime rib, delicacies from the sea, desserts and a late night bar menu. The Fish Whistle also offers a catering and take home menu of delights, and there are excellent specials and events happening all the time, come and enjoy a wonderful dining experience in great surrounds.READ MORE

The Evergrain Bread Company in Chestertown, Maryland offers a passion for baking with delicacies produced by the owner and head baker. With delicious breads, pastries and savories available, enjoy something delightful at the coffee shop with excellent coffees on hand to match your delectable choice, and here you will find the perfect environment to relax and let the world pass you by. Come savour the divine, reconnect and have a moment to yourself in this beautiful space downtown. The Evergrain Bread Company is a gathering place for friends, locals and visitors, where good food and coffee await.READ MORE

Chestertown Historic House offers fine antique furnishings and paintings in keeping with the history of this wonderful home. Enjoy watching the world go by from the porch in the heart of beautiful Chestertown, Maryland, and distant views of the Chester River. This circa 1780 and 1840 house provides a wonderful level of comfort in the master bedroom with his and hers bathrooms, two more bedrooms with private baths, a gourmet kitchen, controlled heating, air conditioning and so much more. Chestertown Historic House also has an outside grill, and is a simply wonderful place to stay as a self catering option when visiting Chestertown, Maryland.READ MORE

Chester River Outfitters in historic Chestertown, Maryland on the beautiful Eastern Shore, offer kayak rental, canoes and accessories as well as bicycle rentals, and are a full service bicycle and paddle shop. Rental boats and kayaks are also offered for sale and you will love paddling and canoeing the beautiful and numerous waterways in the area just waiting to be explored. Scenic country roads are just waiting to be explored by bike, and when renting a bike through Chester River Outfitters, locks and helmets are included. The also have a full-service bike shop for repairs as well as parts in the store. READ MORE