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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.

Waterfront Escape | Sauna+Fire Pit | Kent Narrows

Escape to The Cove at Heron Point, a private 2-acre waterfront retreat in the heart of Kent Narrows. Designed for gathering, unwinding, and making memories. Wake to peaceful waterfront mornings, unwind in our unique greenhouse sauna, gather around the fire pit at golden hour, or settle in for dinner overlooking the water. Perfect for family getaways, couples, girls' weekends and friends looking to reconnect on Maryland's Eastern Shore. Elevate your getaway with curated Signature Experiences!

Private Waterfront Home W/ Hot Tub, Dock & Kayaks

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.

CoastalBeachCottage*BayViews*Close2WeddingVenues

**Close to all the Wedding Venues** Come relax at the all new Coastal Haven Cottage. Take a nice morning walk to the beach &enjoy your coffee while sitting on a bench overlooking the Chesapeake Bay. Light, bright coastal feel inside the home & enjoy the wonderful outdoor space on the deck or in an Adirondack chair around the firepit. Great outdoor dining space to enjoy crabs& large yard for the kids to run. 3 Min Drive to restaurants or walk along the Boardwalk. No addtl visitor/guests allowed

Charming Waterfront Cottage on Historic Property

Enjoy a peaceful get-away in a beautifully renovated, historic cottage. The 115 acre property is on a peninsula with over 2 miles of shoreline. This charming home has water access, trails, a canoe, a hammock, and a lovely grilling patio. The cottage is on the private grounds of Whitehall Mansion, built in 1764 as the home of Governor Sharpe. The farm is used for horse boarding and private weddings. Nearby attractions include Annapolis, the US Naval Academy, Washington D.C., and Baltimore.

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

Bay View Cottage: Perfect for long or short stays

Peaceful cottage and neighborhood, with relaxing views of the bay, close to Annapolis and shopping. Well equipped kitchen and house for long-term or short-term stays...fenced in yard, screened in porch..beach and kid’s park across the street…quiet and relaxing. Community beach (unguarded) to swim or bring your water kayaks or SUPs. Great place to bike as well. Dining and grocery close by. Enjoy the bay views of boats going by, the sound of birds, and great sunsets. Minutes to Rt. 50.

Sunset at Rabbit Run

Sunset at Rabbit Run is a private waterfront 2 acre property located on the Chesapeake Bay with a semi private beach area and fabulous sunsets. Located just outside of the quaint town of Rock Hall with shade trees in the summer. Fish, crab, kayak and swim in the Chesapeake Bay (weather permitting) while enjoying fabulous sunsets, read a book on the hammock or watch the boats up and down the Chesapeake as they enter Rock Hall Harbor. Your family and/or friends will never want to leave.

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.

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 private 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, shopping, trails, and wedding venues.

Waterfront Wellness - *With Pool and Hot Tub!*

Welcome To Paradise! 🌊 Private Beach | 🏊 Heated Pool | 🔥 Sauna | 💦 Hot Tub| 🌅 Sunset Views This Chesapeake Bay retreat features a private beach, heated pool, sauna, hot tub, and guest house in a peaceful waterfront neighborhood. Enjoy coffee on the deck, afternoons swimming or kayaking, and evenings watching sailboats pass as the sun sets over the bay. Just minutes from historic downtown Chestertown, shops, restaurants, and marinas for the perfect Eastern Shore getaway.

Goose Haven, new waterfront house on Fairlee Creek

Goose Haven is nestled on 2 wooded acres on freshwater, Fairlee Creek - about 1.5 hours from Baltimore, Philadelphia, and Washington D.C. It is a very secluded, brand new, 4 BR, 3 BA, waterfront house with direct water access, a dock, and plenty of room to enjoy the outdoors. There is also a public boat ramp/launch right down the road. If you don’t have a boat, don’t worry, we have a kayak & canoe for you to use. Chestertown and Rock Hall are only 20 minutes away.