An aerial view of a town with a river, buildings, and surrounding greenery.

Search and Rent Chestertown Condos

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Chestertown condo rentals

A patio with a round table and chairs, a grill, and a wooden fence.

1. Chapel Gate 3BR Steps to City Dock & Naval Academy

Chapel Gate 3BR Steps to City Dock & Naval Academy
Historic District
$455 nightly
The price is $515
Sep 7 - Sep 8
Total with taxes and fees
Chapel Gate 3BR Steps to City Dock & Naval Academy
A modern interior with large windows, a wooden table, and two potted plants.

2. Luxury Baltimore Escape

Luxury Baltimore Escape
Canton
8.0 out of 10, Very Good, (1 review)
"The location was great so close to where we needed to be. Also very close to shops which was helpful. The kitchen was well appointed. The parking situation was a bit odd but we adjusted. Not sure where the third bedroom was located but luckily our guest did not need accommodations. "
United States
Jennifer R.
$754 nightly
The price is $871
Sep 5 - Sep 6
Total with taxes and fees
Luxury Baltimore Escape
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

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

10/10 Excellent
"Close to the bay"
Joshua 1-night trip
Posted 1 day ago
Best Western Kent Narrows Inn

Find out more about Chestertown

Chestertown Condo Rentals information

Number of reviews
1
Accommodation
4 Condo Rentals
Lowest Price
$515
Highest Price
$871

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 cozy, 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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