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Luxe Modern Chesapeake Waterfront Oasis - 5 Star

The Cottage at Silverwater is a lesson in quiet luxury, compelling architecture, unimaginable views and endless comforts. Original fine art and luxe bedding envelope you in a modern, light-filled space. Outside you will be treated to an expansive waterfront lawn that is great for games and afternoon sun. Rest on modern lounges or watch the sunset on your private waterfront bluestone patio tucked into the sea grass. As a guest favorite, your fabulous getaway is here—just read the reviews!

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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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Sea Dreamer

Tranquil, riverfront, SPLIT LEVEL home, rental is downstairs. 1 bedroom and a patio room can be a 2nd bedroom or living room with 2 pullouts. 3rd space is the Living room with large TV, sleeper sofa, dining and office space, recliner and massage chair! Bath has stand up shower with awesome showerhead, soaps, shampoos, hairdryer and towels. Kitchenette has everything necessary to cook with. BWI 25 min, 45 Annapolis, 60 to DC. Patio , table, grill, lounging sofa, kayaks and beach walks.

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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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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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Waterfront w/ Private Pier, 35 Mins to Annapolis

Located 35 minutes from Annapolis and 45 minutes from Washington DC, Shady Side is a quaint town. This waterfront home is perfect for families or small groups looking to enjoy a relaxing getaway on the Chesapeake Bay. Enjoy the large wrap-around screened in porch and private pier with ladder for easy access for swimming. Large yard, and an incredible view of the Bay Bridge. Free public boat ramp 5 min away in Parish Creek. Listed for 8 people max but contact us for approval of 1-2 more.

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Ft. Smallwood Overlook. Waterfront with Kayaks!

Delightful cottage at the confluence of Rock Creek, Patapsco River (Baltimore Inner Harbor) and the Chesapeake Bay. Adjoins Ft. Smallwood Park with its private coves and beaches. Secluded setting features water on 3 sides with beautiful relaxing views. Teeming with wildlife: ducks, geese, egrets, osprey, eagles, deer, foxes and other. Convenient to Annapolis, BWI Airport, Baltimore & Washington, D.C. Walk to the park. Cast a line, catch what you may! Total renovation 2018-2019.

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Upper Chesapeake Getaway

Come relax with expansive views of the Upper Chesapeake with family or friends. Tucked away in Carpenter's point, you'll find peace watching boats pass by and local wildlife. The newly renovated home features newly 3BR, 1.5 Bath with a fully functional kitchen. You'll enjoy the beautiful sunrise views, water access, kayaks and deck. Local amenities include Great Wolf Water Park, Elk Neck State Park, local restaurants, and Perryville Casino. We welcome you to join the relaxing experience!

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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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Cape St Claire waterfront getaway "The Apartment"

This is a private over the garage apartment located in Cape St Claire, about 5 miles from downtown Annapolis, 2 miles to the Bay Bridge. Private entrance, on site parking, 1- 2 guests. We encourage our guests to enjoy the large back yard patio with magnificent views of the Magothy River and Chesapeake Bay ! Approximately 30 miles to Washington, and Baltimore. 30 minutes to BWI airport. TV and internet. A community beaches just a short walk away. ADULTS ONLY, NO SMOKING, NO PETS.

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Top of the Chesapeake - Private Waterfront Home

Our house is nestled between the shore of the NE River and the creek and marsh directly behind. The home is warm, unassuming and inviting; you'll feel right at home. Perfect for familes or groups, or a romantic weekend. Bird watchers will love the bald eagles, ospreys, kingfishers, mallards and cormorants, to name a few. The upstairs living room is a perfect place for the kids while the adults enjoy the lower area. You find our place warm, cozy and quiet.

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The Shore House

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2 Bedroom on the Water Close to Baltimore and DC

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Chesapeake Houseboat Getaway

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Ruby Of The Bay

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Bay Home in Annapolis with Private Dock

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Beautiful Waterfront Home With Theater Room

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Private Chesapeake Bay Retreat w/ Bay Views!

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Chestertown Watson Family Farm

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Charming RV With A Water View

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Chesapeake Bay View 3BR/2BA Duplex*Spa Tub*

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Chesapeake Bay Estate; 2 Houses, Beach&Heated Pool

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3 Bedrooms of Beachy Bayfront Bliss... PLUS VIEWS!

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Charlestown Cottage at Cattail Bend

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The Bohemia Charmer

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The Cooper House in Charlestown, MD

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Boho River Cottage

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*Waterfront Sunset Bayview* sleeps 6

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Mac's Waterfront Wonder

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Chesapeake Bay Retreat: Couples' Getaway

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Sunset Bay Waterfront cottage on Chesapeake Bay

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