A waterfront town with a pier, dock, and several buildings.

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Chestertown condo rentals

A spacious living room with a stone fireplace, wooden beams, large windows, and a cozy seating area.

1. Breathtaking Mountain Views Surround New Lakefront Condo

Breathtaking Mountain Views Surround New Lakefront Condo
Hague
9.8 out of 10, Exceptional, (106 reviews)
"Everything was great with the place. We believe there was an issue with Expedia as when I accepted and confirmed the reservation, I was charged like I normally was but when I attempted to get any information like an actual address and notification from VRBO they had no record of it and this was the day before the reservation was to start. The people at VRBO were great and I spoke with the host and all was taken care of, but much stress was added when we thought we did not have any...
United States
WILLIAM
The price is €368
includes taxes & fees
20 Oct - 21 Oct
Breathtaking Mountain Views Surround New Lakefront Condo
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

Fort William Henry Hotel and Conference Center

Fort William Henry Hotel and Conference Center

10/10 Excellent
"The facilities were excellent. The views were superb, and the staff couldn’t be more friendly and helpful."
Carol 2-night trip
Posted 1 hour ago
Fort William Henry Hotel and Conference Center

Find out more about Chestertown

Chestertown Condo Rentals information

Number of reviews
106
Accommodation
9 Condo Rentals
Lowest Price
€368
Highest Price
€368

Frequently asked questions

Why book your condo in Chestertown with Expedia?
Reserving a condo in Chestertown is as easy as deciding on your travel dates and picking an option that checks your boxes. In search of something affordable or luxurious, or a stay that also comes with a kitchen and laundry? Use Expedia's search filters to narrow your results even further and find the perfect pad.
How can I find cheap condos in Chestertown?
With Expedia's handy filter tool, locating cheap condos in Chestertown is easy. To find accommodation that are easy on your bank balance, narrow down your search by budget, amenities and star rating.
What is there to do in Chestertown near my condo?
If you're eager to explore the best of Chestertown, find your way to Loon Lake Beach. It's a hit with visitors and locals alike.