Holiday rentals with breakfast in Dorchester County

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Top-rated Holiday Accommodation with Breakfast in Dorchester County

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Guest favourite
A person kneels on a blue paddleboard, surrounded by calm waters under a clear sky. Soft clouds float above, reflecting the peaceful ambiance of the Chesapeake Bay. The shoreline is visible in the distance, enhancing the tranquil setting for outdoor activities.
Hotel room in Oxford
4.9 out of 5 average rating, 31 reviews

Sandaway Suites & Beach Waterfront Hotel Oxford MD

Sandaway Suites & Beach is located in the historic district of Oxford, MD where you can walk to several restaurants and shops. With stunning waterfront views and a private sandy beach on the Eastern Shore of MD rests our boutique hotel. We invite you to stay in one of our beautifully restored water view rooms. Experience in-room comforts and in-town conveniences. Take a day trip to St. Michaels, Easton, or Cambridge. At the end of the day, see an awesome sunset at Sandaway's private beach.

Guest favourite
A charming waterfront hotel is surrounded by vibrant autumn foliage. The spacious lawn is covered with golden leaves, leading to the peaceful shoreline. The building features balconies on the upper floors, and large windows reflect the warm sunlight, enhancing the inviting atmosphere.
Hotel room in Oxford
4.96 out of 5 average rating, 48 reviews

Sandaway Suites & Beach Waterfront Hotel Oxford MD

Sandaway Suites & Beach is located in the historic district of Oxford, MD where you can walk to several restaurants and shops. With stunning waterfront views and a private sandy beach on the Eastern Shore of MD rests our boutique hotel. We invite you to stay in one of our beautifully restored water view rooms. Experience in-room comforts and in-town conveniences. Take a day trip to St. Michaels, Easton, or Cambridge. At the end of the day, see an awesome sunset at Sandaway's private beach.

Superhost
Cottage in Ridge
4.87 out of 5 average rating, 69 reviews

Secluded Waterfront:Kayaks, Sunrises & Unwind

This is a place you come when you need space: real space, quiet, and room to breathe. Set on 18 private acres along the Chesapeake Bay, our Ridge retreat offers a rare kind of calm: uninterrupted nature, open water views, and the feeling of being completely removed from noise, crowds, and schedules-- just land, water, sky, and time. Days unfold slowly with kayaking, crabbing, exploring the land. Evenings end by the fire under dark skies. This is not a tourist destination—it’s a true reset.

Top Guest favourite
Private room in Nanticoke
4.97 out of 5 average rating, 221 reviews

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.

Top Guest favourite
Farm stay in Westover
5 out of 5 average rating, 99 reviews

Big Cozy Loft Overlooking the Farm and River

The cozy loft is located above the apiary workshop. It is a spacious, kind suite with a walk-in bath featuring a rainforest shower. Windows overlook the donkey pasture, river, farm, and gardens. Designed for a true retreat, there is no WiFi, TV, or smoking. For breakfast, travel on over to Sugar Water Restaurant to have a free breakfast with coffee, tea, juice, and more. The Loft includes a small refrigerator plus coffee and tea essentials. Please note: children are not permitted.

Guest favourite
Private room in Trappe
5 out of 5 average rating, 35 reviews

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.

Guest favourite
A vibrant sailboat with a colorful sail glides across the water, surrounded by lush greenery. The scene features a manicured lawn with lounge chairs facing the serene waterway, creating a peaceful view of the idyllic setting.
Hotel room in Oxford
4.95 out of 5 average rating, 60 reviews

Sandaway Suites & Beach Waterfront Hotel Oxford MD

Sandaway Suites & Beach is located in historic Oxford, MD, within walking distance of local shops and dining. Our boutique hotel offers stunning waterfront views and a private sandy beach on the Eastern Shore. Stay in one of our beautifully restored water-view rooms, blending in-room comforts with in-town convenience. Take a day trip to St. Michaels, Easton, or Cambridge, then return to Sandaway’s private beach to experience an unforgettable sunset.

Top Guest favourite
Lawn chairs arranged on a manicured green lawn face the tranquil water, with a sailboat gliding in the distance. A large tree provides shade, completing the peaceful waterfront scene under a clear blue sky.
Hotel room in Oxford
4.93 out of 5 average rating, 61 reviews

Hotel Special: Sandaway Suite & Beach - Oxford, MD

Sandaway Suites & Beach is located in historic Oxford, MD, within walking distance of local shops and dining. Our boutique hotel offers stunning waterfront views and a private sandy beach on the Eastern Shore. Stay in one of our beautifully restored water-view rooms, blending in-room comforts with in-town convenience. Take a day trip to St. Michaels, Easton, or Cambridge, then return to Sandaway’s private beach to experience an unforgettable sunset.

Top Guest favourite
A watercolor painting depicts a serene waterfront scene with boats on the water. A historic yellow building is visible, surrounded by trees and additional structures. The tranquil atmosphere is enhanced by the clear skies and gentle ripples reflecting light on the surface.
Hotel room in Oxford
4.97 out of 5 average rating, 163 reviews

Sandaway Suites & Beach Boutique Hotel, Water View

Sandaway Suites & Beach is located in historic Oxford, MD, within walking distance of local shops and dining. Our boutique hotel offers stunning waterfront views and a private sandy beach on the Eastern Shore. Stay in one of our beautifully restored water-view rooms, blending in-room comforts with in-town convenience. Take a day trip to St. Michaels, Easton, or Cambridge, then return to Sandaway’s private beach to experience an unforgettable sunset.

Top Guest favourite
A large, historic building is seen in the background, framed by bright autumn foliage. A spacious lawn stretches in the foreground, leading to the waterfront. The setting reflects a serene atmosphere with glimmers of water visible beyond the grass.
Hotel room in Oxford
4.93 out of 5 average rating, 162 reviews

Sandaway Suites & Beach Boutique Hotel, Water View

Sandaway Suites & Beach is located in historic Oxford, MD, within walking distance of local shops and dining. Our boutique hotel offers stunning waterfront views and a private sandy beach on the Eastern Shore. Stay in one of our beautifully restored water-view rooms, blending in-room comforts with in-town convenience. Take a day trip to St. Michaels, Easton, or Cambridge, then return to Sandaway’s private beach to experience an unforgettable sunset.

Top Guest favourite
A wooden dock extends over the water, leading to a sun setting on the horizon. Waves gently lap against the sides, reflecting warm hues of orange and pink as the sky transitions into dusk. Two benches are positioned on the dock, inviting peaceful contemplation.
Loft in Lusby
5 out of 5 average rating, 408 reviews

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!

Guest favourite
An aerial view captures the boutique hotel alongside the sandy beach, with lush green trees and well-manicured lawns. Nearby, residential homes are visible, and the tranquil waters of the Chesapeake Bay stretch along the shoreline, inviting outdoor exploration.
Hotel room in Oxford
5 out of 5 average rating, 20 reviews

Sandaway Suites & Beach | Town View Eastern Shore

Sandaway Suites & Beach is located in historic Oxford, MD, within walking distance of local shops and dining. Our boutique hotel offers stunning waterfront views and a private sandy beach on the Eastern Shore. Stay in one of our charming town-view rooms, blending in-room comforts with in-town convenience. Take a day trip to St. Michaels, Easton, or Cambridge, then return to Sandaway’s private beach to experience an unforgettable sunset.

Popular amenities for Dorchester County Holiday Accommodation with Breakfast