Vacation rentals with breakfast in Dorchester County

Treetop Loft Retreat w/ Private Beach Access

Come experience our tucked-away loft 5 minutes from beaches, 10 minutes to Solomons and Calvert Cliffs. Totally private above-garage apartment with 17 stairs. Our open-concept space, has a bedroom area, bathroom, workspace, & kitchen. Enjoy quick Wi-Fi, a 40" Smart TV, a cozy queen bed, and comfy lounge chairs. Choose to stay in or adventure out. NOTE: Smoke-free & peanut-free property as we are allergic to both. Scent Free in your space. Air Purifier. We only use Melaluca cleaning products

A Piece of Paradise

A "Piece of Paradise" is the perfect place to relax. Sit on the dock bench or on the comfy Adirondack chairs and enjoy the view. Bring your kayaks, canoes, or paddle boards which can easily slip into the water from the property. Roaring Point Park and Nanticoke Harbor are just minutes away. Salisbury is about 30 minutes where you can find many restaurants, shopping and touring activities. Two bedrooms connected with a bathroom make it perfect for a family or friends traveling together.

Farm House Stay on the Eastern Shore of Maryland

Sugar Water Manor sits on nearly 115 acres of farm and woods on the Manokin River. Guests have full access to the property including kayaks, fire pit, pool and can make arrangements to enjoy the farm crew, collect eggs and harvest for your meals. A breakfast treat will be delivered each morning . The Farm House has the best views of the property.  With views of the river, garden, both barns and farm you will not know where to look first.  Unplug- no WiFi/TV or smoking on property.

The Anchorage Bed & Breakfast

B&B Use Permit No. BB 23-1 Welcome to the Maryland Eastern Shore! Your home away from home is a room in a late Federal Telescopic Tidewater Style Bed & Breakfast called The Anchorage, circa 1800 facing the Choptank River. There are also 3 other rooms available at the B&B if traveling in groups or with family members. We are located right outside the historical town of Trappe very close to Easton, Oxford, Cambridge, and St. Michaels. Rooms include a daily continental breakfast.

Black Walnut Cove Retreat, Tilghman Island

Our waterfront studio retreat is a birdwatchers paradise. Located on beautiful Black Walnut Cove at the southern tip of Tilghman Island, you will be in a quiet neighborhood surrounded by water. Enjoy a quiet walk or bike ride along the Chesapeake Bay shoreline. You will have access to our dock and small boat ramp. Crabbing and fishing are a delight. Please note: 1) There is a 3-nt. minimum on holiday weekends. 2) Children between the ages of 1 and 5 are not permitted

The Anchorage Bed & Breakfast

B&B Use Permit No. BB 23-1 The Anchorage is a late Federal Telescopic Tidewater Style B&B circa 1800 facing the Choptank River. It's a waterfront property with gorgeous views of the water and a private beach. Special March Rates!! There are also other rooms available if traveling with other people. We are located right outside the historical town of Trappe very close to Easton, Oxford, Cambridge, and St. Michaels. Rooms include a daily continental breakfast.

Talbot Corner: Dog-Friendly 3-Bedroom Home

No cleaning fee, plenty of space, quiet neighborhood! Escape to this charming, single-level home with 3 bedrooms, a separate office (with doors), high-speed wifi, a large FENCED-IN backyard (very pet friendly!), garage, and a patio with picnic table. Gas fireplace, fully-equipped kitchen, washer/dryer, plenty of parking! Two blocks to the river and park, great for bikers, runners and kayakers.

Comfortable Twin Sofa Bed

Home is 10 years old, bright and airy open concept. Kitchen access, shared bathroom. We are located about 1 mile from Historic downtown Cambridge, Maryland and 1.6 miles from Gerry Boyle Park. (Ironman and Eagleman Triathalon start site) Known for great restaurants, local seafood, and RAR brewery, unique shops and boat marina.

The Anchorage Bed & Breakfast Mayflower

Located on the mighty Choptank River, The Mayflower features a comfortable King Size bed wi-fi, table with 4 chairs, and a private bathroom with a shower. There is also a fridge, coffee maker, blender, and dishes. We also offer a waterfront setting, kayaks, breakfast, a pool that is open seasonally, and plenty of space to relax.