
Holiday rentals in Caroline County
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Top-rated holiday rentals in Caroline 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 Caroline County holiday rentals
Other great holiday rentals in Caroline County
Guest favourite

Home in Preston
4.96 out of 5 average rating, 93 reviewsRiver House on the Choptank
Top guest favourite

Home in Greensboro
4.97 out of 5 average rating, 89 reviewsCozy 2 bedroom home on wooded private lane
Superhost

Home in Denton
4.9 out of 5 average rating, 87 reviewsHistoric 19th Century Eastern Shore Farmhouse
Superhost

Cabin in Goldsboro
4.85 out of 5 average rating, 145 reviewsWigwam Lodge ~ HotTub ~ MasterSuite~Woodland Views
Top guest favourite

Farm stay in Centreville
5 out of 5 average rating, 36 reviewsNo Fees~Historic Lansdowne Manor
Top guest favourite

Home in Greensboro
4.97 out of 5 average rating, 152 reviewsCozy Riverside Cottage in the Woods
Top guest favourite

Home in Preston
4.98 out of 5 average rating, 65 reviewsBay Country Cottage

Home in Preston
4.44 out of 5 average rating, 27 reviewsLITTLE CREEK HIDEAWAY
Destinations to explore
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- Miami Beach
- Sandy Point State Park
- Big Stone Beach
- Dewey Beach Access
- Patterson Park
- Oriole Park at Camden Yards
- Heritage Shores
- Six Flags America
- Cape Henlopen State Park
- Willow Creek Winery & Farm
- Delaware Seashore State Park
- Killens Pond State Park
- M&T Bank Stadium
- Gerry Boyle Park
- Peninsula Golf & Country Club
- Towers Beach
- Quiet Waters Park
- Maryland Renaissance Festival
- Crystal Beach Manor, Earleville, MD
- Bulle Rock Golf Course
- Plantation Lakes Golf and Country Club
- Baywood Greens Golf Maintenance
- Poodle Beach
- Idlewilde Restoration Project