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*Waterfront Sunset Bayview* sleeps 6

Welcome to our beautiful, completely renovated waterfront home in the heart of Kent Island! Our home has magnificent direct sunset views, that force you to stop and take it in! Our open-concept home is tastefully decorated with a blend of modern amenities and cozy charm, complete with large windows that allow natural light to fill the space along with stunning views of the Bay. Escape the hustle of everyday life and immerse yourself in the serene beauty from the comfort of your private retreat.

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River Front, Private Single Family Home

Soak in the waterfront hot tub or sit around the waterfront fire pit in this one story completely renovated house w/ 3 bedrooms and 2 full bath. One master bedroom with private bathroom and one bathroom for the rest of the house. Tv in each room and expansive views of the Chester River. There are tons of outdoor activities to do from fishing, kayaking, paddle boarding and biking. This is a gorgeous piece of property on Maryland’s eastern shore. Great crab houses and restaurants minutes away

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Bay Breeze Retreat

Incredible private luxury retreat on the eastern Chesapeake Bay. Complete with every amenity- saltwater pool, firepit, multiple Smart TVs, sleeps 10 in comfort, premium memory foam mattresses in every room, fast Wi-Fi, 100' pier, huge front yard. Unbelievable views!!! Extensively renovated. Please note that no parties or disturbances will be tolerated. We require that guests respect our neighbors and serene community at all times. We explicitly do not allow bachelor or bachelorette parties.

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Rivershore Retreat

Escape to Maryland’s Eastern Shore where the pace of life is slower and nature surrounds you. Mid-century modern A-frame with artfully curated décor and a well-appointed kitchen has drop-dead gorgeous river views and its own waterfront and dock. The house sits on a large, private acre lot with plenty of room for kids to play. Short walk to downtown Chestertown with its Farmer’s Market, restaurants and galleries. A perfect get-away for artists, writers or families seeking a low-key vacation.

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Beachside Dream

Kick back and relax in this calm, stylish space, 4 bedroom 3 full bathroom, Sandy Beach front, stunning sunset. An hour from DMV. Wall of windows in the Living Room overlooks the evening sunsets on the Bay. Sun room with the stunning views of bay. Spacious rooms for up to 12 guests($50 charge per guest after 8 guest) 10 minute drive from popular wedding venues, Chesapeake Bay Beach Club and Silver Swan. Hotel quality linens and towels are provided, unlimited High Speed WIFI , 3- Smart TV

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25-50% Off~Private Beach~Hot Tub~Fire Table~

Welcome to our Chesapeake Bay Cottage on Kent Island, Maryland! This unique 3 bed 2 bath home with luxurious amenities is a perfect getaway for families or friends looking to create unforgettable memories and experience all the Bay area offers. Escape the hustle and bustle with an easy commute from Annapolis, Washington and Baltimore. The Naval Academy is right across the Chesapeake Bay Bridge. Adventure and relaxation are within easy reach from any mid-Atlantic and northeastern location.

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Kent Island Haven - A Waterfront Getaway

Located across the bay from Annapolis, Kent Island Haven is a convenient and beautiful alternative to a hotel. Near shopping, nature areas, and walking trails; as well as the fine restaurants and water-oriented features of the Eastern Shore. Convenient to Baltimore, DC, Easton and St. Michaels. This 600 square foot 1 BR/1 BA in-law apartment has a private entrance and full kitchen. Watch the ships and ospreys from the living room. Enjoy the waterside hammock, pier, patio, and garden.

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Country House on the Bay

My home (owner occupied/shared) sports a spectacular view of the Chesapeake Bay with access to the beach. The home is spacious with a family, dining, breakfast and living room. Significant kitchen space is available with all of the cookware and place settings you would need for a meal. The master bath is handicapped accessible. My deck can be used for cookouts and relaxation. Hosting a gathering - lets talk- my home is perfect for celebrations. Close to Annapolis & Naval Academy.

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Private Chesapeake Bay Retreat w/ Bay Views!

Step into a relaxing retreat at this picturesque vacation rental on Chesapeake Bay! Complete with 2 bedrooms and 2 bathrooms, this spacious home offers a cozy fireplace and a stunning deck overlooking the water — perfect for enjoying the sunset! Explore the nearby Eastern Neck National Wildlife Refuge or take a scenic drive to the quaint shops and seafood restaurants in town. Whether you're seeking outdoor adventures or a peaceful coastal getaway, you’ll love this Rock Hall property!

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Bay Home in Annapolis with Private Dock

Complement your next outing to the Annapolis area with a stay at our beautiful waterfront home primely situated on the Chesapeake Bay! Featuring a well-equipped modern kitchen, deck with outdoor dining area, separate comfortable outdoor seating area, an outdoor fire pit, and dock with 4 adirondack chairs to enjoy the sunsets with a beverage of your choice. Stroll through Sandy Point State park and visit the Colonial Annapolis Historic District and the Annapolis Maritime Museum.

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Quaint Waterfront- access, Private Shorehouse-unit

Location is everything in this comfy and affordable private unit located on the Chester River and Winchester Creek with water views. Also enjoy the hosts water front amenities such as fishing at our private pier, boating, kayaking, paddle boarding or simply relax at the waterfront for morning coffee and sunrises or enjoy the fire pit in the evening. The community playground and beach are just steps away. Close proximity to restaurants and shopping.

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Bayside bungalow cottage by the sea

This quaint Cottage is located on a quiet residential road with quick access to the water. Located in Rock Hall, Maryland, guests will enjoy a getaway from the hustle and bustle of major cities. The Cottage boasts 1 bedroom and 1 bathroom, equipped with a private sauna. Guests are guaranteed to have a relaxing stay here at the Cottage House! Great views of Swan Creek and the Cheseapeake Bay.

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Chestertown Watson Family Farm

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Entire River Front Home - 4 Bedrooms 4.5 Baths

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Chesapeake Houseboat Getaway

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River Front, Private Single Family Home

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Rivershore Retreat

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Bay Home in Annapolis with Private Dock

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Love Point Waterfront

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Private Chesapeake Bay Retreat w/ Bay Views!

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Charming RV With A Water View

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Unwind at this Waterfront Retreat

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Waterfront stay in Kent island

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Bay View Beach Cottage, perfect for long-term

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Crab Alley Bay House, Waterfront Home w Hot Tub

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CoastalBeachCottage*BayViews*Close2WeddingVenues

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Charming Waterfront Cottage on Historic Property

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Goose Haven, new waterfront house on Fairlee Creek

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The Birdhouse on Swan Creek, Welcome!

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Bayou on the Bay

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Due East Bay Cottage

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