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Check prices for these dates

In two weeks
10 Oct - 12 Oct
In two months
21 Nov - 23 Nov
In three months
19 Dec - 21 Dec
In four months
16 Jan - 18 Jan
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
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, (284)
"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, (36)
"The condo is very nice, nice. Everything we needed. Hoping for another stay in the near future."
BEACH WITHOUT THE BUSTLE
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

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

10/10 Excellent
"Great location and rooms. Great place!"
Ana 3-night trip
Posted 1 day ago
Hyatt Place Kent Narrows & Marina

Find out more about Chestertown

Find out more about Chestertown

Chestertown Condo Rentals information

Number of reviews
290
Accommodation
4 Condo Rentals
Lowest Price
Highest Price

Frequently asked questions

Why book your condo in Chestertown with Expedia?
We think that getaways should be hassle-free, so if you're in search of condos at an affordable rate, Expedia can help. Keep the budget in check and choose something small and cosy, or book a luxury condo and treat your loved ones. Take advantage of our search filters to find a stay in Chestertown that fits your needs.
How can I find cheap condos in Chestertown?
Expedia can help you narrow your search for cheap condos in Chestertown. To find a superb stay in just a few clicks, simply use our convenient filter tool to tailor your search results by star rating, budget and amenities.
What is there to do in Chestertown near my condo?
The most practical travel accessory is a well-planned itinerary. Rolphs Wharf Marina is a good place to start your exploration of Chestertown.

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Explore a world of travel with Expedia