Simply Bed and Bread is a wonderful guest house in Chestertown located close to the water and with two gracious rooms available you'll feel right at home. Enjoy a convenient stay close to the college campus, wonderful gifts shops and fine restaurants nearby and historic sites, and the area is perfect as a wedding destination with old world charm, as well as fishing, golfing, biking, birding and so much more. Simply Bed and Bread extends a warm welcome, and a wonderful stay is guaranteed. 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

O'Connor's Pub and Restaurant in Chestertown, Maryland is an Irish style pub and restaurant that offers traditional and delicious Irish and local food, with generous portions and beautiful presentation. O'Connor's Pub and Restaurant offers a premium full bar too and visitors can enjoy a fine Irish whiskey, imported and domestic beers and arguably the best Guinness in town. The legendary Crab bisque soup, oysters and Maryland crab cakes, are award winning meals, and daily specials are also available. O'Connor's Pub and Restaurant caters to private events in the function room and courtyard, available for up to 150 patrons, come party.READ MORE

Visit Lauren Ames Interiors in Chestertown for decor, interior design, comfortable designsREAD MORE

Robert Ortiz Studios in Chestertown, Maryland offers handmade and contemporary furniture in the Shaker and Japanese Traditions, custom crafted from exquisite woods. Here you will find exquisite chairs, tables, cabinets and beds that are unique, pleasing to the eye and a must have, perfect for the enhancement of any home or office, and the ideal corporate gifts, a purchase from Robert Ortiz Studios will have guests talking. Robert Ortiz Studios goal is to bring out the best in wood, and this they do with a skill and mastery that is breathtaking.READ MORE

Chestertown Natural Foods in Chestertown, Maryland offers natural and organic food and products, here you will even find vitamins and unique gifts. Striving to provide the best gourmet products available, Chestertown Natural Foods has knowledgeable personnel, is handicap and wheel chair accessible, caters to everyone and invites you to buy fresh and buy local. Services include nutrition consultation by appointment, speaking engagements, free educational literature, even free coffee and tea on a Saturday, a wide range of offerings and organic produce, and a whole lot more.READ MORE

Brooks Tavern in Chestertown offers an eclectic mix of rustic and hip, and is housed in the historic site of the Radcliffe Mill, and they are open Tuesday through Saturday for lunch and dinner. Come eat, drink, relax and enjoy a wonderful dining experience in warm and hospitable surrounds, where good service and great food is the order of the day. The menu is seasonal and one to be proud of and here there is something delicious for everyone, and the wine list is in constant motion, come and enjoy a delight at Brooks Tavern, you'll be back.READ MORE

The White Swan Tavern in Chestertown, Maryland is a historic site and landmark since the pre-revolutionary war days, and is nestled in the Chesapeake Bay Region. Enjoy new world tradition, peace and tranquility in this wonderful bed and breakfast that offers gracious afternoon teas and cater to private events like small conferences, weddings, and receptions. White Swan Tavern offers rooms and suites some with four poster beds, and old world charm, and there are two fully equipped apartments known as the Bittersweet Guest Suites available too. Start your day with a continental breakfast in your room or their tea room, and enjoy a free morning newspaper, WIFI, cable TV in the sitting room and so much more, come feel the history, and enjoy the privacy here, it's wonderful.READ MORE

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

The Imperial Hotel in Chestertown is the perfect gathering place for travelers and locals, with a delightful front room restaurant and bar serving eclectic contemporary cuisine. Here you can enjoy comfortable accommodations in the 11 deluxe rooms and 2 suites with balances of old world charm, quaintness and modern amenities. Private events are catered to here with meeting rooms, banquets and private dining available it's perfect for wedding receptions too. The Imperial Hotel offers wine tastings, and hotel packages, and an unforgettable stay is guaranteed.READ MORE