Family-friendly vacation rentals in Dorchester County

Church Creek Charm (Close to Blackwater!)

Charming Eastern Shore home built in 1900, located in CHURCH CREEK, MD, less than 10-15 mins from Cambridge, Blackwater National Wildlife Refuge & the Harriet Tubman Underground Railroad museum. Ideal spot for cycling, birding, fishing, canoeing, relaxing, or exploring the many cute towns of Maryland's Eastern Shore. Just over an hour from Ocean City & Assateague Nat'l Seashore. Pet-friendly with a fenced backyard. The Eastern Shore is famous for its seafood, history, nature & fresh produce!

Madison Nature Getaway

We're on 106 acres minutes away from Cambridge, Blackwater NWR, Harriet Tubman URR State Park and two public boat ramps for access to Chesapeake Bay. Hike our trails and enjoy bird watching, wildlife photography and fishing on our award winning tree farm and relax by our pond. Bring your bikes, binoculars and kayaks and enjoy the surrounding area. We have a gas grill and a screened pavilion for our guests for parties and meals. FRIENDS OF BLACKWATER NWR MEMBERS & MILITARY RECEIVE A 10% DISCOUNT.

Nature's Rest in Church Creek

Nature's Rest is located just minutes from Blackwater Wildlife Refuge, The Harriet Tubman Museum, Blackwater Adventures! Boat ramps are close by for easy access to the Chesapeake Bay and its tributaries for enjoying Maryland's Eastern Shore. We have plenty of parking, so bring your boat, bikes, and binoculars. Just mins from downtown Cambridge for dining & shopping. Discover the many quaint towns the area has to offer, come for a night, or stay as long as you'd like, look forward to meeting you.

Waterfront with sweeping bay view & private beach

Year-round private beach oasis on Chesapeake Bay! Perfect Fall & Winter Escape. An hour from DC beltway & world away. Recharge & relax to the sound of waves & sailboats. Spacious & fully renovated, with modern features, ample outdoor terraces. Enjoy long walks, nature spotting (bald eagles, rays, dolphins), shark tooth collecting. Kayaks provided! Short drive to Solomons Island, and local amenities: restaurants, bars, store, national parks & vineyards. No parties or events. Only relaxing.

Soul Oasis - home on the Chesapeake Bay

Listen to the waves of the Chesapeake Bay from the trex deck. There are 2 private community beaches in the neighborhood where you can find fossils and sharks teeth. A great place to relax and unwind. You will hear the sounds of all kinds of birds, see lots of very tiny frogs in spring and summer and maybe some deer around the house! You can also expect to see/hear aircraft from Pax River Base fly overhead! Book your stay today and let the magic of the woods and water wash away your cares.

The Little House on the Farm, Water Access

Peaceful, Quaint & located on the Little Blackwater River, & 1.5 miles from the Blackwater National Wildlife Refuge & The Harriet Tubman Underground Railroad State Park & Museum. A bird watching, kayaking, and bicycling paradise awaits. Perfect for a couples retreat, girls getaway or a solo vacation to relax & unwind. Hunters and Fishermen are welcome also! Route 50 & downtown Cambridge are 10 mins away for local eateries and shopping! This is the perfect location to explore the Eastern Shore!

Sunset Breezes - quiet waterfront retreat

Enjoy well equipped waterfront home styled after historic lighthouses. Relax in the hammock by the water under the pines; Enjoy smores by the fire pit. Wood included. Free use of 4 kayaks, 2 paddleboards, and a 3 person canoe. Yard games include corn hole, croquet, & bocce. Dine on the deck while enjoying beautiful sunsets. Bring your cameras for local wildlife. NEW Fun & Fitness Barn: sauna, golf simulator, free weights, game space and more. Ask about access code and hours.

Blackwater & Snakehead Farm "She Shed" Tiny House

The "She Shed" Tiny House is the best bargain & unique stay around! This Tiny House is made from a traditional 10'x18' shed and is solar powered! It's surprisingly spacious with a full size bathroom, kitchenette, lofted twin bed, day bed & trundle bed! The home borders a sheep pasture, barn, goat pasture & chicken coop! Snakehead fishing is just a short walk away! Kayacks & creek launch on site! Just a 5 minute drive from Blackwater Refuge! Relax and enjoy country living!

Waterfront Getaway with Dock

Bicyclist's and outdoorsman's dream! Beautiful rancher on two waterfront acres just 4 miles from Blackwater Wildlife Refuge and Harriet Tubman National Park. 10 minute drive from downtown, the Hyatt, and the Ironman starting point as well. Ironman and Eagleman races actually pass right by! Bright, sunny, and newly renovated, it's a great place to hang your hat after a day of hunting, fishing, bicycling, or triatholon-ing! Or just take a weekend to relax on the water!

Relaxing Beach Getaway Loft near Solomons

Note: We are a peanut-free property. RELAX in our chic, private loft just 5 minutes from Chesapeake beaches and 10 minutes from Solomons Island & Calvert Cliffs. You will have private access to our amazing beach just a five minute drive away. Enjoy our private, above-garage hideaway apartment with private beach access, fast WiFi, Smart TV, and cozy touches that make you feel at home. You have a private entrance. Come and go as you please!

Cove Point Lighthouse Keeper's House- Side A

Listed on the National Register of Historic Places and cared for by the Calvert Marine Museum (CMM), the Cove Point Lighthouse historic site has been lovingly restored and re-purposed so that it can be enjoyed by all. The active lighthouse and keeper's home sit on a seven-acre point of land in one of the narrowest points of the Chesapeake Bay.

Charming Farmhouse 2 miles Historic St. Marys City

- Conveniently located within 2 miles of Historic St. Mary's City and St. Mary's College of Maryland - Farm with sweeping views of the fields and ponds - Relax under cafe lights on patio - Need more room, ask about the adjacent studio apartment.