Skip to content

Vacation rentals in Caroline County

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Caroline County

Guests agree: these stays are highly rated for location, cleanliness, and more.

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

Other great vacation rentals in Caroline County

Private room in Hurlock
Peaceful Queen-Bed w/ Beautiful Farmland Views
$55 per night
Home in Preston
River House on the Choptank
$165 per night
Private room in Denton
Riverton Retreat (queen bed)
$89 per night
Home in Denton
Historic 19th Century Eastern Shore Farmhouse
$195 per night
Rental unit in Greensboro
Awesome River House Waterfront Apartment
$182 per night
Home in Hartly
Hartly House in the Country 10 min West of Dover
$150 per night
Home in Greensboro
Cozy Riverside Cottage in the Woods
$235 per night
Farm stay in Centreville
Lansdowne Manor
$250 per night
Place to stay in Denton
Turnbridge Manor
$500 per night
Home in Preston
$293 per night
Rental unit in Greensboro
Newly Renovated Entire Apartment in Cottage
$285 per night
Private room in Hurlock
#3 Beautiful Farm Views - Queen + Private Office
$55 per night