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

Search Condo Rentals in Chestertown

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Chestertown condo rentals

TV

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

Chapel Gate 3BR Steps to City Dock & Naval Academy
Historic District
10.0 out of 10, Exceptional, (1 review)
"Very cute home in great proximity to naval academy"
United States
JENNIFER E.
Chapel Gate 3BR Steps to City Dock & Naval Academy
Interior

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.
The price is AED 1,818
AED 3,199 total
includes taxes & fees
25 Sep - 26 Sep
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chestertown Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

8/10 Good
"Lovely set of historic inns. The setting was perfect to explore downtown Annapolis (Maryland Inn). We would have preferred a lower floor with more space in lieu of the top floor which was a bit tight for two. Very little natural light in the room. The rooms could have used water (only offered a $12 bottle!) and sufficient coffee cups for two (received only 1)"
Jamie 2-night trip
Posted 2 hours ago
Historic Inns of Annapolis

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.

Explore a world of travel with Expedia