
Holiday houses in Dorchester County
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Top-rated holiday rentals in Dorchester County
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
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Popular amenities for Dorchester County holiday rentals
Other great holiday rentals in Dorchester County
Guest favourite

Cabin in Church Creek
4.96 out of 5 average rating, 28 reviewsCharles Creek Cabin

Cottage in Wingate
4.83 out of 5 average rating, 81 reviewsBlue Crab Cottage: Remote+Nature+Fishing+Views
Guest favourite

Cottage in Fishing Creek
4.95 out of 5 average rating, 21 reviewsThree Anns / EV charger,screened porch,water views
Top Guest favourite

Home in Madison
5 out of 5 average rating, 32 reviewsMadison Bay Club House

Home in Nanticoke
4.58 out of 5 average rating, 19 reviewsKayaker and Fisherman's Pit Stop
Top Guest favourite

Home in Cambridge
5 out of 5 average rating, 23 reviewsCharming cottage, 1 blk water, historic area
Top Guest favourite

Home in Oxford
4.98 out of 5 average rating, 63 reviewsStunning Chesapeake waterfront home
Guest favourite

Home in Fishing Creek
5 out of 5 average rating, 12 reviewsMaravillosa casa frente al mar
Destinations to explore
- Apartment rentals Dorchester County
- Rentals with a washing machine and dryer Dorchester County
- Rentals with pools Dorchester County
- House rentals Dorchester County
- Rentals with beach access Dorchester County
- Waterfront rentals Dorchester County
- Rentals with lake access Dorchester County
- Rentals with a hot tub Dorchester County
- Beachfront rentals Dorchester County
- Rentals with a fireplace Dorchester County
- Rentals with a kayak Dorchester County
- Family-friendly rentals Dorchester County
- Rentals with a patio Dorchester County
- Rentals with a fire pit Dorchester County
- Cottage rentals Dorchester County
- Pet-friendly rentals Dorchester County
- Rentals with breakfast Dorchester County
- Rentals with outdoor seating Dorchester County
- Sandy Point State Park
- Six Flags America
- Plantation Lakes Golf and Country Club
- Breezy Point Beach & Campground
- Piney Point Beach
- Ragged Point Beach
- Quiet Waters Park
- Chesapeake Beach Water Park
- Rose Haven Memorial Park
- Sandyland Beach
- Heritage Shores
- Gerry Boyle Park
- St George Island Beach
- Saint Jerome Beach
- Franklin Manor Community Private Park
- Flounder Pavilion Beach Front - Sandy Point State Park
- North Beach Boardwalk/Beach
- Bayfront Beach
- Matapeake Clubhouse and Beach
- Guard Shore
- Idlewilde Restoration Project
- Marshalls Beach
- Lake Presidential Golf Club
- Brownies Beach