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Guests savor the unhurried timeless quality of this rural watermen's village where an earlier and friendlier way of life continues to thrive. Guests are invited to enjoy breakfast al fresco on the rear patio or to simply view the garden.
Upstairs over the store in downtown Chestertown.
Overlooking picturesque Rock Hall Harbor, we offer five comfortable guest rooms and complimentary dockage for overnight guests arriving by boat.
Discover a historic and award-winning bed and breakfast in Chestertown, MD. This romantic inn is situated on 35 beautiful acres with glorious views and delicious breakfasts! Unforgettable rooms offer whirlpool tubs, fireplaces, and flat-screen TVs.
A delightfully intimate hideaway vacation spot in a quaint fishing village near the Chesapeake Bay. Enjoy stunning water views while being close to great restaurants and quaint shops. We are just a hop, skip and a splash from the Public Beach.
Enjoy a unique farm experience: walk the trails on our 365 acre farm, enjoy views of the vineyard, experience a wine tasting, stay in our Inn...about an hour from Philadelphia, Baltimore, Washington DC, minutes from Chestertown.
Elegant 12 room waterfront manor house with enchanting sunsets over the Chesapeake Bay on Maryland's Eastern Shore.
Haven Point Inn & Gallery is a new contemporary inn and gallery with beautifully appointed rooms designed with your comfort in mind. A complimentary delicious country breakfast will help you start your day.
Conveniently located within a short (5 min) walking distance of the main town of Rock Hall and adjacent to the resort amenities of Haven Harbour Marina, the Inn at Haven Harbour exudes the nautical luxury and charm of a boater's paradise.
A true wildlife habitat at this elegant, four-season farm estate with 1100 ft. of glorious waterfront. First class accommodations and full country breakfast. Lovely gardens, walking paths and inviting saltwater pool. Pet and family friendly cottages
Beauty undisturbed. Historic manor offers a tranquil retreat. Approximately 10 miles outside of Chestertown.
At Osprey Point Inn, Restaurant and Marina, you'll experience the perfect fusion of luxurious accommodations, elegant dining, and a relaxed and friendly environment.
Gothic Revival Victorian, fully restored. Full breakfast and afternoon tea. Within blocks of the Historic District of Chestertown.
Come by car or by boat. Moonlight Bay Inn hugs the shore of the beautiful Chesapeake Bay. Whether you are watching the everchanging scenes on the bay or meditating in the English Garden, each view is a painter's paradise.
Spend a night – or a weekend – in charm and comfort. With views of the Chester River and the adjoining farm, the River Inn at Rolph’s Wharf offers you the opportunity to spend a relaxing night or two away from the everyday. Each of the rooms has its
Two allergy-friendly rooms in a cozy 1947 Cape Cod - a minute's walk from Washington College. "The soul should always stand ajar," [ready to welcome] - Emily Dickinson
A delightfully secluded B & B at water's edge a short distance from the quaint little fishing village of Rock Hall. Luxurious accommodations in delightful seclusion with kayak and sailing adventures at your doorstep.
We are minutes from Washington College, the 10th oldest college in the United States. Highlight your stay with the fine dining and tapas bar menu at The Kitchen at The Imperial.
Victorian gem located in Chestertown's Historic District
