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Check prices for these dates

In two weeks
Feb 20 - Feb 22
In two months
Apr 3 - Apr 5
In three months
May 1 - May 3
In four months
May 29 - May 31

Our top choices for Chestertown condo rentals

Dining

Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
$622 nightly
The price is $709
Feb 8 - Feb 9
Total with taxes and fees
Historic Row Home in Downtown Annapolis
Property grounds

Luxe Row Home Steps to USNA Gate 3!

Luxe Row Home Steps to USNA Gate 3!
Historic District
$535 nightly
The price is $610
Feb 8 - Feb 9
Total with taxes and fees
Luxe Row Home Steps to USNA Gate 3!
Interior

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
Feb 9 - Feb 10
Total with taxes and fees
Luxury Baltimore Escape
4 bedrooms, iron/ironing board, travel crib, WiFi

Two Historic Rowhomes in Downtown Annapolis

Two Historic Rowhomes in Downtown Annapolis
Historic District
$803 nightly
The price is $915
Feb 9 - Feb 10
Total with taxes and fees
Two Historic Rowhomes in Downtown Annapolis
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

Hampton Inn Baltimore Bayview Campus

Hampton Inn Baltimore Bayview Campus

10/10 Excellent
"Yes room was great"
Anthony 1-night trip
Posted 4 days ago
Hampton Inn Baltimore Bayview Campus

Find out more about Chestertown

Chestertown Condo Rentals information

Number of reviews
Accommodation
4 Condo Rentals
Lowest Price
$709
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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