
House vacation rentals in Dorchester County
Find and book unique houses on Airbnb
Top-rated house rentals in Dorchester County
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Dorchester County house rentals
House rentals with a pool

Family Retreat - Private Pool, 4 Bedroom, Fire Pit

Waterfront Paradise with a Private Pool

Gorgeous, waterfront home - Perfect for Families.

Spacious and private waterfront, sleeps 10

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit

Peaceful Waterfront Home with Pool and Pier

Turtle's Nest - Hist. Cambridge

Pet-Friendly Stay with Pool – Relax & Unwind!
Weekly house rentals

Aurora Blue - A stylish experience

Beachfront Oasis with Amazing Views

Water views, w/BBQ, patio, near downtown& beach!

Spacious Historic Craftsman only 3 blocks to water

Holliday House

Waterfront with sweeping bay view & private beach

Hambrooks House - Porched Sanctuary near Choptank

WaterfrontHotTubPvtPierFirePitKayakGrillQuietHouse
Private house rentals

Spacious Lakefront Cottage w/ Private Pier

ChesapeakeWaterfront - HotTub_FirePit_Kayak_Arcade

Waterfront, amazing views, pier, fishing/crabbing

Charming 4 bedroom in Historic Cambridge

• Peaceful Point • A relaxing waterfront retreat

Ye Ole Pirate House

Walk to the Beach and Find Shark's teeth!

SoMD Waffle House 1.5 acres of cozy coastal living
Destinations to explore
- Beachfront rentals Dorchester County
- Rentals with a washer and dryer Dorchester County
- Rentals with a fire pit Dorchester County
- Rentals with beach access Dorchester County
- Waterfront rentals Dorchester County
- Rentals with lake access Dorchester County
- Apartment rentals Dorchester County
- Pet-friendly rentals Dorchester County
- Cottage rentals Dorchester County
- Rentals with a patio Dorchester County
- Rentals with breakfast Dorchester County
- Rentals with a hot tub Dorchester County
- Rentals with outdoor seating Dorchester County
- Rentals with a kayak Dorchester County
- Kid-friendly rentals Dorchester County
- Rentals with pools Dorchester County
- Rentals with a fireplace Dorchester County
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- Sandy Point State Park
- Maryland Renaissance Festival
- Six Flags America
- Quiet Waters Park
- Plantation Lakes Golf and Country Club
- Heritage Shores
- Gerry Boyle Park
- Piney Point Beach
- Breezy Point Beach & Campground
- Chesapeake Beach Water Park
- Sandyland Beach
- Bayfront Beach
- Rose Haven Memorial Park
- Idlewilde Restoration Project
- Matapeake Clubhouse and Beach
- Brownies Beach
- Quiet Waters Dog Beach
- Saint Jerome Beach
- Oxford Beach
- Lane Beach
- North Beach Boardwalk/Beach
- Franklin Manor Community Private Park
- Lake Presidential Golf Club
- Triton Beach