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.
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!
The Brampton Bed and Breakfast Inn offers guests a romantic setting one mile from historic Chestertown on Maryland's Eastern Shore. This Maryland bed and breakfast is a meticulously restored 1860 manor house featured on the National Register of Historic Places. We are nearby popular shops, waterfront dining, and the Garfield Center for the Arts. Our inn features 13 luxurious accommodation options ranging from rooms, to suites, to a pet-friendly apartment. What better way to complement your visit to the Chesapeake Bay region than to surround yourself with the beauty of an 19th-century estate on Maryland’s Eastern Shore! All rooms are exceptionally spacious and well-appointed with comfortable furnishings. You will enjoy the park-like view of the landscaped fruit, vegetable and flower gardens surrounding this romantic B&B. An à-la-carte breakfast is served each morning, and afternoon tea between 4 and 5.
Hummingbird Inn is located in a beautiful, circa 1865 Queen Anne Victorian in the heart of Easton, Maryland’s historic district. Blending the best of Victorian style with modern comfort, the Hummingbird Inn is welcoming, hospitable, and so much more than just a place to sleep. We’re a quick, two-block walk from Easton’s boutique shops, restaurants, galleries, and theater, and short a ride to boating, beaches, and all the Eastern Shore attractions. Hosting an Event? Hummingbird Inn’s stately architecture, lush landscape, and extensive Victorian gardens offer a striking, spacious venue Relax, meet new friends, discover the beauty of the Eastern Shore. Hummingbird Inn is a stately Queen Anne Victorian with a striking copper-roofed turret, lush gardens, and wrap-around porch. Hummingbird Inn blends the grandeur of the past with modern features and comfort.
Reynolds Tavern Bed & Breakfast is one of the finest examples of Georgian architecture in Annapolis. Situated in a prominent position on Church Circle in Maryland it is convenient to the historic district, shops, restaurants and the United States Naval Academy. Reynolds Tavern features 3 Private Overnight rooms on the Second floor of the Tavern. There is a Cellar Pub (1747 Pub), 2 dining rooms on the first floor and a large outdoor Beer Garden. Many events are held outside in the Beer Garden through the Spring, Summer and Early Fall. The Annapolis Shakespeare Company performs on Tuesday evenings, Trivia Night every Monday Night, and Free outdoor Movie Screenings on Sunday Evenings. Live Music Wednesday through Saturday evenings.
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.
This Rock Hall, MD bed and breakfast offers luxurious rooms and accommodations in Maryland. Enjoy a continental breakfast, and private waterfront balcony, and whirlpool tub. Our bnb in Rock Hall has pools, bikes, kayaks, paddleboards and more without sacrificing quality or service. Book your stay today! Click our link above to Book Direct for your next beach escape in Rock Hall, Maryland.
In the heart of the historic district, Gatehouse of Annapolis Bed & Breakfast overlooks the US Naval Academy. From our convenient location you can walk to St. John's College, and City Docks... The Gatehouse of Annapolis is a classic Georgian-style townhouse that has been lovingly refurbished to provide guests with an atmosphere of comfortable elegance The Gatehouse of Annapolis is an oasis for the connoisseur of travel.
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.
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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.
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!
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.
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!
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.
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!
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.
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.
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