Holiday rentals with breakfast in Dorchester County

Heron's Nest: Yoga & Writer's Retreat

Shoeless, hippie-vibe cottage on Lake Charming. Quiet setting, prvt beaches, near all SoMD beauty, farm-table cuisine. Perfect retreat for bff’s, single women wanting peace, marriedwomen wanting peace, 💕couples, itinerant profs, 🧘‍♂️yogis, dancers, writers, birders. About Barefoot laughter, "slow food," health & wellness, movement, music, mediation, peace & sanctuary. Lic.thx offers: Sound Therapy, Feldenkrais Method™ & crystal healings. 420 & LGBT+Friendly. Healing4healers. Incense burned here.

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.

Chic Loft Retreat | Private Beach & Near Solomons

STAY IN or ADVENTURE OUT Relax in a chic, private loft just 5 minutes from Chesapeake beaches and 10 minutes from Solomons & Calvert Cliffs. Enjoy your own private above-garage hideaway with private beach access, fast WiFi, Smart TV, and cozy touches that make you feel at home. Our open-concept space, has a bedroom area, bathroom, workspace, living room & kitchen. SMOKE FREE SCENT FREE PET FREE PEANUT FREE We offer an Air Purifier and use only all natural cleaning products.

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.

Big Cozy Loft Overlooking the Farm and River

Located above the apiary workshop, the Loft is a spacious kind suite with a walk-in bath featuring a rainforest shower. Windows overlook the donkey pasture, river, farm, and gardens, Each morning, a farm-fresh breakfast is delivered. The Loft includes a small refrigerator plus coffee and tea essentials. Designed for a true retreat, there is no WiFi, TV, or smoking. Please note: children are not permitted.

Farm House Stay on the Eastern Shore of Maryland

Set on 115 acres along the Manokin River, Sugar Water Manor invites guests to enjoy kayaks, the pool, fire pit, and even join the farm crew to collect eggs or harvest produce. A breakfast treat is delivered each morning. The Farm House offers the property's finest views--river, gardens, barns, and fields all around. Unplug during your stay, as there is no WiFi, TV, or smoking on the property.

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.

Trust-n-travel

Totally Mystified by Trust n Travel Memories Soak up Marvelous Memories with a smile as your Magical Moments and Magical #famvacations are forever Mystical. so, as you look back at your fabulous time shared vacationing with "Trust n Travel" Entrust your stay, your moments, and your memories.

The Anchorage Bed and Breakfast Skipjack

Located on the mighty Choptank River, The Skipjack features a comfortable King Size bed, a large couch, mini fridge, coffee maker, wi-fi and a private bathroom with a shower. We also offer a beachfront setting, kayaks, breakfast, a pool that is open seasonally, and plenty of space to relax.