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Kent Island Beach House - "Pink" House in Kentmorr

KI Beach House – 1,800 sq ft. Chesapeake Bay water views. Across from Channel Side (previously Kentmorr Beach Bar & Restaurant), Kentmorr Marina & charters, and minutes to local wedding venues & Matapeake Beach. Perfect for holidays, wedding accommodations, small family gatherings, fishing trips, or golf getaways. Features 4 bedrooms/3 baths (4th is a large family room with smart TVs & fireplace), kitchen, open dining/living, spacious deck, huge yard, and your own private beach volleyball court.

Private Beach Front Marina House

Beautiful waterfront property with private beach shared with one other family, ideal for family gatherings, located within walking distance of Kent Point Marina and convenience store. Enjoy a relaxing evening with family and friends sitting on the outdoor patio overlooking the Chesapeake Bay. You will have exclusive views of fresh-caught crabs & fish as they come off the boats during Summer. If you enjoy crabbing, fishing, boating, kayaking, swimming - it can all be done from this property.

Charming RV With A Water View

Indulge in a waterfront paradise in our inviting stationary RV rental on the Chesapeake Bay. Sleeps 2 adults + 2 children with a queen bed + queen sleeper sofa. Positioned on the bay for easy water access and breathtaking sunset views. Enjoy the shared use of a heated pool, grill and pier. Experience swimming, fishing, crabbing and outdoor fun right at your RV "home." Close to wedding venues, marinas, charter fishing, dining spots, golf courses, parks, and biking trails and Annapolis and D.C

Private Waterfront Cottage with Pool and Poolhouse

Totally Private, quiet, deep water-front cottage with wood-burning fireplace and exclusively private 60' Lap Pool (open mid-April to mid-October), large open Pool House and Pier. The nearest residences in the area are far removed from this cottage for a great feeling of seclusion and privacy at cottage, pool, lawns, and gardens; all for the exclusive use of cottage guests. Located between the beautiful villages of Easton and Cambridge -- close to Trappe, Oxford, and St. Michaels. STRN-26-13

Cozy Cottage

Escape to this beautiful cottage overlooking the Chesapeake Bay. Just steps from the beach, this getaway offers water views right from the comfort of the living room. The interior has been remodeled and stylishly furnished, with two bedrooms and one bathroom. This cottage is perfect for couples, small families, or a peaceful solo retreat. Minutes from Downtown Annapolis, the Naval Academy, and other points of interest. NOTE: currently doing yard work; the backyard does not have grass yet

Heide's GuestHouse

Pairing modern comforts with timeless charm, this 1-bath studio offers an ideal stay on your next visit to coastal Cambridge. Visit the Harriet Tubman Museum, dine on fresh local seafood, or enjoy a leisurely stroll along the Choptank River — all just steps from your front door. Back home, rest and relax on the shared patio, or curled up in front of the TV. Traveling with a pet, or maybe a larger crew? Make use of this vacation rental's pet-friendly policy and additional rental home on-site.

Waterfront Gem < 1 Mi to Dtwn Cambridge!

Walkable Location | Close to Shops & Breweries Turn your getaway dreams into reality right on the water! This 1-bed, 1-bath vacation rental offers direct access to the Choptank River, promising spectacular sunsets and effortless fishing or kayaking. After strolling through local parks and museums, retreat indoors for a movie or game night. Perfect for couples heading to Maryland's Eastern Shore, this Cambridge apartment places history, outdoor fun, and downtown hot spots just moments away!

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

High Water Guest House

Second floor apartment overlooking the Cambridge Creek and the beautiful Choptank River. Ideal location at the end of historic High Street and adjacent to the city marina. Walk to downtown for shopping and dining. Take advantage of having a front row seat to the finish line of Ironman Maryland. Beach, pier and large yard made available for your use. Two inflatable paddleboards, one inflatable kayak and one inflatable 2 seater kayak available for use. Limited size life jackets available.

Osprey's Retreat Waterfront w/ private beach/dock

Enjoy a weekend escape or extended vacation for up to 6 guests at this freshly renovated gem located on LeCompte Bay . Beautiful waterfront property with a private sandy beach, located just 5 minutes outside of town with plenty of outside activities including a dock and fire pit. Super clean & comfortable, modern home & furnishings featuring a first floor premier, well appointed kitchen. This home is provided with everything you need for a fun, relaxing get-a-way on the Bay.

Cottage at Goose Neck Point

Romantic one bedroom, one bathroom waterfront cottage with direct access to the Tred Avon River. Beautifully renovated interior. Spacious living areas and kitchen. Gorgeous water views from all rooms. Home features a screen porch and sun porch. It’s a short drive from restaurants, local shops, specialty stores and farmers market. Just minutes from Easton and St. Michael’s. Bikes are available for guest use. 3 night minimum stay Talbot Co. STR#ST-261-HAR

Sandaway Suites & Beach Boutique Hotel, Water View

Sandaway Suites & Beach is located in historic Oxford, MD, within walking distance of local shops and dining. Our boutique hotel offers stunning waterfront views and a private sandy beach on the Eastern Shore. Stay in one of our beautifully restored water-view rooms, blending in-room comforts with in-town convenience. Take a day trip to St. Michaels, Easton, or Cambridge, then return to Sandaway’s private beach to experience an unforgettable sunset.