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Vacation rentals in Caroline County

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Top-rated vacation rentals in Caroline County

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

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.
$150 per night
Bungalow in Queen Anne
Adorable 2-bedroom bungalow near Easton, Tuckahoe
- High-speed Internet - Premium Samsung washer and dryer - Fire Pit - Level 2 EV Charger - Two (2) cruiser bicycles - Memory foam mattresses - Full kitchen - Smart TV - Quiet, secluded space with easy access - 5 minutes to Denton - 15 minutes to Easton - 15 minutes to Centreville - 30 minutes to St. Michaels Located just minutes from both Easton and Tuckahoe State Park, you'll have endless opportunities for outdoor adventure.
$160 per night
Cabin in Goldsboro
Wigwam Lodge~Hot Tub~MasterSuite~Woodland Views
Wigwam Lodge is an experience nestled in a pine & hard wood forest with rural privacy. Incredibly spacious decks. Surround Forest Views inside and out! 5-min from Choptank river, 20-min from Historic Denton, Irish Pub & Grocery, 1hr from the beach. Easy PARKING 10ft from the front door. Solid WIFI! Click “Show More” Below to SEE ALL Deets...
$186 per night

Other great vacation rentals in Caroline County

Home in Denton
Mallard Landing Townhouse
$132 per night
Home in Preston
River House on the Choptank
$185 per night
Private room in Hurlock
#2 Beautiful Farm Views - Queen + Walk In Closet
$59 per night
Private room in Hurlock
Cheerful Queen-Bd, in Beautiful Eastern Shore, MD
$55 per night
Home in Hartly
Hartly House in the Country 10 min West of Dover
$156 per night
Private room in Denton
Riverton Retreat too ( 2 twin beds)
$89 per night
Cottage in Denton
Choptank River Shore Cottage
$139 per night
Home in Denton
Historic 19th Century Eastern Shore Farmhouse
$195 per night
Farm stay in Denton
Lyford Landing Farmhouse
$250 per night
Home in Queen Anne
Farmhouse w/hot tub, close to Tuckohoe State Park
$785 per night
Home in Greensboro
Cozy Riverside Cottage in the Woods
$235 per night
Farm stay in Centreville
Lansdowne Manor
$375 per night

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