logo

Bed and Breakfast Chestertown MD

If you are a history lover, fond of small-town charm, gas-lit lanterns  and charming cobblestone streets, you should visit the quaint town of Chestertown, Maryland, to enjoy the wonders that Maryland’s Eastern Shore has to offer.

Bed and Breakfast Chestertown MD

Carefree Elegance on the Chesapeake Bay on Maryland's Eastern Shore, Great Oak Manor is a magnificent Georgian Mansion sitting on the banks of the Bay. The beautiful lawns and landscaping create openness while remaining private. Our B&B has 12 guest rooms and a spacious Carriage House that is perfect for families. Our private beach allows our canoe, kayaks and paddle boards easy access to the water. Take our cruiser bicycles out for a ride on our flat country roads or choose to relax in our Adirondacks by the water or nap in one of the hammocks. Our evening sunsets are not to be missed!

Nearby Properties

This Odessa, DE bed and breakfast offers luxurious rooms and accommodations in Delaware. Enjoy a wholesome homemade breakfast, and private baths, and free WiFi. Our bnb in Odessa provides a unique rural small town feel and big city conveniences within reach without sacrificing quality or service. Book your stay today! Click our link above to Book Direct for your next peaceful escape in Odessa, DE.

The best location in Annapolis! Welcome to Gibson's Lodging's of Annapolis--an Inn located in the heart of the Annapolis Historic District & 1 block from the city dock and many great restaurants. Park your car in our courtyard and walk to everything!

Laurel Grove is a luxury Bed and Breakfast in Annapolis, MD. It is an 8,400 sq. ft. cedar and stone contemporary home on three acres overlooking the South River.

Next to the harbor and the Chesapeake Bay Maritime Museum, just two blocks from the main street of St. Michaels.

Perfect for vacation getaways or weddings, and located in historic Havre de Grace, Maryland.

This North East, MD bed and breakfast offers luxurious rooms and accommodations in Maryland. Book your stay today! Click our link above to Book Direct for your next getaway in North East, MD.

Welcome to the Inn at 2920; A downtown Baltimore inn with a distinctively contemporary style. Leisure and business travelers enjoy comfortable guest rooms with flat screen HDTV’s, private limestone bathrooms, free Wi-Fi and sumptuous full breakfasts. Inn at 2920's location offers easy access to all of Baltimore's attractions by foot, by car, or by the Water Taxi on the Harbor just two blocks away.

Offers seclusion, while allowing easy access to many activities, Peninsula House is located in the maritime district called Eastport, just a short walk past all the best waterfront resturants to city dock and main street shops.

Welcome to the Bay Breeze Inn in Rock Hall, MD dating back from the 1920's and was a favorite with Eastern Shore goose hunters who stayed at the Old Crosby Property"."

The Annapolis Inn Bed & Breakfast is in a prime location on stately Prince George Street in the Historic District of Annapolis. The inn is surrounded by elegant mansions and is just steps away from the U.S. Naval Academy, St. John's College, the City Dock, the Maryland State House, and so much more. There's no need for a car, just comfortable walking shoes!

This Annapolis, MD bed and breakfast offers luxurious rooms and accommodations in Maryland. Book your stay today! Click our link above to Book Direct for your next getaway in Annapolis, MD.

The Inn at Huntingfield Creek is a well-appointed bed and breakfast situated on 70-acres of land with Chesapeake Bay views. featuring comfortable rooms with fine linens, plush robes and towels, down comforters and private bathrooms. The harmonic atmosphere of the inn is perfect for weddings, family vacations or a romantic retreat with guest rooms, cottages and a vacation rental available for lodging. Enjoy panoramic views of the countryside, pet-friendly rooms, spa baths with whirlpool tubs and much more. Maryland’s Eastern Shore region is well known for its many nature preserves, fishing/crabbing, marinas, antique shops and areas of historical interest. As the Inn at Huntingfield Creek is the closest inn to the wonderful Eastern Neck National Wildlife Refuge, it’s easy to spend an entire day walking the trails, snapping photos or viewing the resident Bald Eagles and tundra swans enjoying the wonders that Chesapeake Bay has to offer.

The Historic Sinking Springs Herb Farm & Retreat is set on 130 beautiful rural acres in Elkton, Maryland. Come explore the gardens and hear the history of an 18th-century provincial plantation house. See the ancient sycamore tree which sprouted in 1578. As part of the 2 1/2 hour program, sit down to an herbalicious gourmet delight – a luncheon of fresh, unprocessed food prepared with herbs and served in the original house. Or if you prefer, we also offer a program, “Herbs of the Bible” with a Labyrinth Serenity Walk. Afterward, if you wish, browse the gift shop, which offers herbs and dried flower creations. It’s a perfect secluded getaway – great for honeymooners of all ages! We also offer a private cottage garden for intimate picnics or enjoy a cozy warm fire (also electric heat) to snuggle by. Then relax & enjoy a leisurely breakfast (your choice) surrounded by the beauty of Sinking Springs.

The Blue Max Inn Bed & Breakfast in Chesapeake City, MD offers a luxurious atmosphere for business meetings, romantic getaways, and friends vacationing. All of our king and queen guest rooms and suites are custom with wireless Internet, private baths, and gourmet breakfasts. Working fireplaces, a beautiful dining room, and a relaxing parlor with a grand player piano are just a few of the features of this elegant B&B. The inn’s convenient location is along the Chesapeake and Delaware Canal in the northeastern corner of Maryland, within easy reach of Philadelphia, New York, Baltimore and Washington, D.C.

Located on Maryland's Eastern Shore of the Chesapeake Bay between St. Michaels and Tilghman Island. Come join us in our island like setting and watch our spectacular sunsets. Offering waterfront guest rooms, restaurant, patio bar, marina, charter fishing, sunset cruises, crabbing, kayaking, or just sitting back on our private beach watching the sunset.

Explore Bed and Breakfasts in Chestertown, MD

You should know that historic Chestertown is situated in Kent County on Maryland’s famous Eastern Shore.

The town was founded in 1706 and named one of Maryland's 6 "royal ports of entry" in the early eighteenth century. Soon after the 1773 Boston Tea Party, citizens of Chestertown decided to prohibit selling, buying, or drinking tea. Also, they even held their tea party on the idyllic Chester River, which is a sight to behold.

Today, you can see Chestertown’s  rich and vibrant colonial history along places like the historic  waterfront, High Street, and the fantastic replica Schooner Sultana. The  enchanting and scenic coastline of Chestertown varies from historical waterfront towns elegantly dotted  with marinas of various sizes to charming stretches of low and rolling  farmlands that are broken only by the pretty tributaries of the famous Chesapeake River. Note that this beautiful land, where salt and fresh water meet,  is certainly a haven for boating and fishing enthusiasts, birders,  cyclists, and nature lovers.

If you are in town, you can visit the Garfield Center for the Arts, which preserves the cultural significance and legacy of Chestertown's historical Prince Theatre.

If you are a bed and breakfast lover, you are in luck! This is because Chestertown has many charming B&B’s that you can choose for an ideal romantic getaway. Chestertown, MD bed and breakfast have friendly and knowledgeable innkeepers and comfortable accommodations that you might never want to leave.

Bed and Breakfast Chestertown, MD, such as Great Oak Manor,  offer you the perfect hideaway, providing an excellent fusion between  the modern and traditional with a great dedication to service. You will  also like Bed and Breakfast near Chestertown, MD, like Bay Breeze Inn, as they help you get away from the bustle and commotion of daily life.

    Natural Features

  • Do you often find yourself hopping from one confined space to the other?  If yes, it might be a suitable time to reset in nature! You can make  the most of your vacations by spending a day by the gorgeous Chester River or Blackwater National Wildlife Refuge and recharge in the fresh air!

  • Activities

  • Did you know that Chestertown is also the gorgeous county seat of Kent County? The town is one of Maryland's Eastern Shore's most influential and earliest settlements. If you are in Chestertown, you should visit some grand houses built by affluent merchants that line the scenic Chester River.

    Among  the city's best and most notable historic buildings are the Wide Hall  and Hynson-Ringgold House. The latter is known for its extraordinary and  distinct antler staircase as well as a hip roof that will leave you  dazzled.

    You will be happy to know that the Historical Society of Kent County provides a variety of informative history tours that focus on specific and vital aspects of this town’s unique heritage.

    Also,  Betterton beach is an ideal spot for swimming as well as family  picnics, while lovely and serene coves tucked along the amazing  peninsula provide you with excellent opportunities for canoeing,  fishing, or kayaking. You can also rent kayaks. You should know that MassoniArt Gallery is worth visiting. It is the vision of the acclaimed and respected Chesapeake Bay-area gallerist Mr. Carla Massoni.

    Some other tourist hotspots in the area are Rock Hall and Emmanuel Chester Parish, and you will also like private beaches, such as Tolchester Beach. It is worth noting that Chestertown, MD, is also the home of the prestigious Washington College.

  • Things to do

  • If you are in Chestertown,  you can also enjoy many annual festivals as well as annual events, such  as the RiverFest Arts Festival and National Music Festival. For  example, the yearly Chestertown Harry Potter Festival is great and is a blast for both young and old  fans. It is no secret that this festival benefits the art community and  includes many events, such as scavenger hunts, a Quidditch tournament,  charms classes, and a costume contest that you and your family will  love.

    You can also engage in some retail therapy! This is because historic Chestertown is also brimming with unique local boutiques and shops where you’ll  find countless amazing creations. There is certainly no better place to  be if you are a shopaholic!

  • Food and Drink

  • Regardless of what you are in the mood for, note that Chestertown, Maryland,  has a cafè or restaurant serving up quality by the plateful. For  example, the shopping centers along the famous Route 213 and downtown Chestertown provide you with a variety of excellent options.

    You  can also visit Figg's Ordinary. It seamlessly brings the rich colonial  dining practice of ordinaries into the modern-day. Some other options  are Casa Carmen, Aroma, and Luisa’s.

Bed and Breakfast Chestertown MD FAQ

background flowers
  • Why stay at a Bed & Breakfast in Chestertown, MD?

    After exploring the best sites and destinations in Chestertown, you should treat yourself to an amazing and relaxing night of pure leisure at a B&B in Chestertown. These inns offer unparalleled services and hospitality.  You can check-in to one of these B&Bs to make the most of your vacation rentals.

    Some countryside and elegant inns along Maryland's eastern shore and the Chesapeake Bay, such as Rock Hall, offer a storied past, perfect manor house architecture, heated bathroom floors, and other premium amenities that you will not find in big hotels.

    Other bed and breakfast inns are close to Chester River and Washington College and feature state of the art kitchens, Jacuzzis, gas fireplaces, and comfy spa tubs!

  • What type of amenities can I expect when booking a Chestertown Bed and Breakfast?

    You will enjoy many amenities by staying at a bed and breakfast in Chestertown, MD. Most inns provide services like free Wi-Fi, lovely guest rooms and dining rooms, king or queen beds, central air conditioning, and private baths. These services will make your getaway more memorable.

    If you are looking for more privacy, you can check-in to an inn with boutique hotel rooms that offer screened-in porches.  Many B&Bs also offer a full breakfast, afternoon tea, snacks, and  brandy, ensuring that you are well cared for throughout your stay, which  is amazing.

  • What are the different types of B&Bs in Chestertown?

    There are many types of B&Bs in Chestertown,  MD. The best thing is that you can enjoy a remarkable breakfast and  other amenities, such as elegant fireplaces, on par with some of the big  hotel chains. For example, romantic bed and breakfast Chestertown, MD, offers luxurious rooms and accommodations so that you and your partner can enjoy some intimate time.

    Some great options are Brampton bed and breakfast inn and Great Oak Manor. These inns offer you a romantic and cozy setting just a mile from historic Chestertown. The private beach at Great Oak Manor allows the canoes, paddleboards, and kayaks easy access to the water. Are you looking for a pet friendly bed and breakfast Chestertown,  MD? If yes, you will not be disappointed. Some of these inns feature  luxurious accommodation options that range from rooms, and large suites,  to pet-friendly apartments.

    You can also stay at Mitchell House and White Swan Tavern and enjoy comfortable rooms with plush robes, fine linens, and towels.

    The bnbfinder Diamond Collection is a prestigious and exclusive group of highly-rated or professionally inspected luxury bed and breakfasts and inns.

    And  all members of the bnbfinder Diamond Collection have to pass a  professional inspection performed by an industry-recognized inspection  agency. Don’t forget to inform the innkeeper you found them through the bnbfinder Diamond Collection!