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Old Bay Bungalow

This in-law apartment located in the lower level of my occupied home is just moments outside of Annapolis, mere blocks from the Magothy River. I enjoy inviting guests into the space, and take pride in treating new friends like family. Come rest your weary bones in your private retreat with its own separate entrance, relaxing sunporch, and stocked kitchenette. Reach into the fridge and enjoy cold soda or a local beer on me! Sit around our fireplace and relax. Settle into the Old Bay Bungalow!

Beautiful Waterfront Chestertown Getaway

Lovely three room waterfront guest suite conveniently located less than 10 minutes from historic Chestertown and Washington College. Beautiful views of our tidal creek, full kitchen, wooded lot, quiet neighborhood, bird watching, kayaking, great biking & running options. Friendly pets (indoor cats and dogs who can share the yard with us and our dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice.

The Oxford House

Enjoy water views from the backyard or visit with friends on the screened in porch. The light and airy, 3bd, 2bath house is a short walk to Oxford’s best restaurants and favorite ice-cream shop. You can find the best beach in oxford only 75 yards from our front door or take the Ferry to the neighboring town of Saint Michaels, Maryland. You will love the scenic views and historical charm of this little town, the Oxford house has a central location allowing you to walk or bike to everything.

Nautical Charm and relaxing waterview!

Our comfortable and relaxing studio is a quiet retreat with a fantastic view while still in close proximity to Washington DC, Annapolis and Baltimore! Situated in a charming waterfront and sailing community, this separate and private unit has: parking, 1 bath, queen bed, kitchen (limited), TV, high speed WiFi and Bluetooth speaker. Wake up to the cluck cluck of our four resident chickens who are tucked away in their attractive coop. Sit on the porch and take in the view!

Stunning Lake House Retreat on the Potomac River

This beautiful lakeside home offers the perfect sanctuary for your next retreat, nestled along the Potomac River just two hours from the D.C. metro area. It is spacious enough for any large family gatherings or groups of friends. Lounge with a gorgeous view or start a ping pong/pool game. Whether embarking on your next fishing adventure, kayaking, biking, playing yard games or simply relaxing in our luxurious jacuzzi, your visit will surely be one to remember.

SM’s Premier Rental Heated Pool opens 4/11/2025

Harbor Hideaway's in- town location and now featuring a PRIVATE POOL is a rare find. Steps away from everything that SM's has to offer. HH is a 1940’s - 1 1/2 story cottage loaded with thoughtful amenities. Airy and appointed with modern/ comfortable furnishings, resort quality linens, a well stocked kitchen; this 2 bdrm /2 B cottage is sure to please! Perfect for 1 to 2 couples, girls' wknds, small family, or anyone just in need of a relaxing getaway.

Walk to famous Tiki Bar on Solomons Island!

Cute studio apartment on charming Solomons Island. Walking distance to restaurants, live music, boat and kayak rentals. The kitchen has a full sized refrigerator, microwave, toaster, two burner hot plate and coffee maker. We provide all bedding and bath towels for two people. Enjoy your coffee ( provided) or wine on the deck in the fenced in side yard. One well-behaved pet is welcome. Please make sure you pay the pet fee.

Historic Rousby Hall, Waterfront, Pool, Beach

Rousby Hall is located on the Patuxent River, outside of Solomons Island with a view of the river's opening to the Chesapeake Bay. The 16-acre property is adjacent to our very private conservation area that borders our 300-foot private beach. The year-round property has a pier, and in-ground pool (May-October) with amazing river views. Also hosts weddings+events up to 100 guests (additional event fee applies).

"Wittman Cottage"

Wittman Cottage is located on a beautiful stretch of waterfront views. It is a very nice vacation spot for the family. You can relax and watch the beautiful sunsets from our very large screened porch, or drive to shop and dine in St. Michael's and visit the Maritime Museum which is only 7 miles away..