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Vacation rentals in Dorchester County

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Top-rated vacation rentals in Dorchester County

Guests agree: these stays are highly rated for location, cleanliness, and more.

Gettin to the point. ( Cove Point Beach)
SUPERHOST
Entire cottage · 4 guests · 2 beds · 2 baths

Gettin to the point. ( Cove Point Beach)Our beach house is for you to enjoy Cove Point Beach, which is only 500 ft away. The kitchen is fully stocked, or use the outdoor grill on the deck. PLEASE NON SMOKERS ONLY. NO PETS ALLOWED. No large parties registered guests only, no children under 8 years old. We provide a binder with all local restaurants and things to do and enjoy. Walk the beach look for shark's teeth, sea glass. Relax on our large deck, or enjoy the firepit. Parking allowed only in the driveway.

NEW LISTING! Renovated Waterfront Cambridge Escape
Entire residential home · 9 guests · 4 beds · 2 baths

NEW LISTING! Renovated Waterfront Cambridge EscapeBrand new listing! Serene, newly renovated waterfront home is ready for your next getaway! Perfect for families, couple trips, and work-from-home scenery changes. Our home is furnished with every amenity to make your experience as enjoyable and stress-free as possible. Enjoy bird watching, crabbing, fishing, and picturesque sunsets from the private pier, relaxing by the fire pit, and family game nights in the spacious living room. Minutes from charming downtown Cambridge.

Adorable Waterfront Apartment Weekend Getaway
SUPERHOST
Entire rental unit · 2 guests · 1 bed · 1 bath

Adorable Waterfront Apartment Weekend GetawayBright & cheery 1 bedroom waterfront apartment nestled on the banks of the St. Mary's River. Amazing, dreamy views. It's a sweet spot to relax and enjoy a quiet get-away or launch a kayak, take a walk, enjoy great food cuisine. We sit next to St. Mary's College of MD and Historic St. Mary's City. You may see college sailing races, crew teams rowing, or the historic Maryland Dove sailing down the river. It's lovely here fall, winter, spring, summer! SUNSETS!

Vacation rentals for every style

Get the amount of space that is right for you.

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Popular amenities for Dorchester County vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Dorchester County

SUPERHOST
  1. Entire guest suite
  2. Cambridge
Sailwinds Waterview Loft at Cambridge Creek
  1. Entire cottage
  2. Fishing Creek
Fishing Creek waterfront cottage
SUPERHOST
  1. Farm stay
  2. Westover
Farm House Stay on the Eastern Shore of Maryland
  1. Entire rental unit
  2. Cambridge
Water front view 1 - bedroom efficiency apt
SUPERHOST
  1. Tiny house
  2. Saint Inigoes
Historic St.Mary's City at the Lazy Bear Cottage
  1. Entire guesthouse
  2. Lusby
Lakeside Studio Retreat
SUPERHOST
  1. Entire cottage
  2. Westover
Experience complete relaxation on the water.
SUPERHOST
  1. Entire guesthouse
  2. Cambridge
"Happy Campers" Waterfront Apartment!
SUPERHOST
  1. Entire residential home
  2. Lusby
Cove Point Cottage 1 block from Chesapeake Bay
SUPERHOST
  1. Entire cottage
  2. Deal Island
Water View Cottage
SUPERHOST
  1. Entire rental unit
  2. Church Creek
Church Creek Natures' Rest
SUPERHOST
  1. Tiny house
  2. Cambridge
Blackwater Tiny Cabin on Snakehead Creek