Vacation rentals in Caroline County

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Top-rated vacation rentals in Caroline County

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Bungalow in Queen Anne

Adorable 2-bedroom bungalow near Easton, Tuckahoe

Looking for a peaceful retreat on the Eastern Shore? Our cozy bungalow is the perfect choice for families or solo travelers looking to explore the natural beauty of the area. Located just minutes from both Easton and Tuckahoe State Park, you'll have endless opportunities for outdoor adventure. When you're not exploring the surrounding area, enjoy the convenience of our dedicated work area. And when the night falls, gather around our outdoor fire pit and make memories that will last a lifetime.

$151 per night

Home in Greensboro

Cozy 2 bedroom home on wooded private lane

Take it easy at this unique and tranquil getaway. Located on a quiet country lane this 2-bedroom home offers comfort and privacy on a wooded lot. Plenty of parking. Enjoy all that the Eastern Shore has to offer from this central location convenient to Easton, Dover, Chestertown, Rehoboth, Denton and Ocean City. Beautiful views from front and back porches, full kitchen, two full baths. Great getaway for 1 or 2 couples. Pets allowed with prior permission and additional deposit.

$125 per night

Home in Denton

Mallard Landing Townhouse

Welcome to Maryland’s Eastern Shore and your own private townhouse in a quiet and peaceful neighborhood. You’ll be conveniently located less than an hour to the beaches, with short travel to Dover and Easton. But why bother traveling when your in the beautiful historic town of Denton and all it has to offer with many up and coming stores, restaurants, and many other sights to enjoy including the Choptank River, Martinak State Park, Tuckahoe State Park, and historic downtown.

$113 per night