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Condo Rentals in Chestertown

Annapolis Condominium in the heart of the historic center
Terrace/patio

Annapolis Condominium in the heart of the historic center

9.8 out of 10, Exceptional, (281)
"The location and amenities are great. The host are very friendly, helpful and easy to make contact with. My family used this location for commission week and could not have asked for more. "
Annapolis Condominium in the heart of the historic center
Kent Island Waterfront Cottage
Fridge, microwave, oven, stovetop

Kent Island Waterfront Cottage

8.8 out of 10, Excellent, (11)
"Enjoyed fishing at the pier and sitting on the porch"
Kent Island Waterfront Cottage
BEACH WITHOUT THE BUSTLE
Marina

BEACH WITHOUT THE BUSTLE

10.0 out of 10, Exceptional, (33)
"Wanted to book something for a little quiet getaway. This place was absolutely amazing! Thank you so much ! It was exactly what I was looking for! "
BEACH WITHOUT THE BUSTLE
Unique 2-Bedroom Condo in Renovated Church Parish House
Marina

Unique 2-Bedroom Condo in Renovated Church Parish House

Unique 2-Bedroom Condo in Renovated Church Parish House
Waterfront condo. Completely renovated. Walk to Kent Island's best places
TV, fireplace

Waterfront condo. Completely renovated. Walk to Kent Island's best places

Waterfront condo. Completely renovated. Walk to Kent Island's best places
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chestertown Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Charming area and loved to hotel decor!"
Elizabeth 3-night trip
Posted 5 hours ago
Historic Inns of Annapolis