
Waterfront holiday rentals in Dorchester County
Find and book unique waterfront rentals on Airbnb
Top-rated waterfront rentals in Dorchester County
Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for waterfront rentals in Dorchester County
Waterfront apartment rentals

Waterfront Room at Happy Campers

Happy Campers Waterfront Suite

Cambridge Apt in Walkable Neighborhood

Farm View Room at Happy Campers
Waterfront house rentals

Reel Relaxation-Waterfront

Coastal Oasis On The Chesapeake, King Bd sleeps 12

Starboard on McKeil Point, w/heated pool & hot tub

Waterfront, Private Pier, Sleeps 10, 4 bedrooms

Gorgeous, waterfront home - Perfect for Families.

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit

Spacious Gorgeous Waterfront Home with Sunset View

Stunning Chesapeake waterfront home
Other waterfront holiday rentals

La Cabaña

On the river beautiful original Chesapeake home!

Waterfront Cottage & Guesthouse Near Cambridge

Pizza Friday

Rodo Beach Cottage - Dog Friendly Private Beach wi

Cottage on Cabin Creek

• Peaceful Point • A relaxing waterfront retreat

Chesapeake Bay Retreat! Spectacular Views!
Destinations to explore
- Rentals with a kayak Dorchester County
- Cottage rentals Dorchester County
- Rentals with a fireplace Dorchester County
- Rentals with beach access Dorchester County
- Rentals with a hot tub Dorchester County
- Family-friendly rentals Dorchester County
- Pet-friendly rentals Dorchester County
- Rentals with a washing machine and dryer Dorchester County
- Rentals with pools Dorchester County
- Flat rentals Dorchester County
- Rentals with breakfast Dorchester County
- Rentals with a firepit Dorchester County
- House rentals Dorchester County
- Rentals with lake access Dorchester County
- Beachfront rentals Dorchester County
- Rentals with outdoor seating Dorchester County
- Waterfront rentals Maryland
- Waterfront rentals United States
- Sandy Point State Park
- Six Flags America
- Plantation Lakes Golf and Country Club
- Piney Point Beach
- Breezy Point Beach & Campground
- Quiet Waters Park
- Ragged Point Beach
- Chesapeake Beach Water Park
- Rose Haven Memorial Park
- Gerry Boyle Park
- Saint Jerome Beach
- Heritage Shores
- North Beach Boardwalk/Beach
- Bayfront Beach
- St George Island Beach
- Franklin Manor Community Private Park
- Guard Shore
- Idlewilde Restoration Project
- Matapeake Clubhouse and Beach
- Lake Presidential Golf Club
- Brownies Beach
- Marshalls Beach
- Oxford Beach
- Triton Beach