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

Search and Rent Chestertown Condos

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Chestertown condo rentals

Living area

1. Breathtaking Mountain Views Surround New Lakefront Condo

Breathtaking Mountain Views Surround New Lakefront Condo
Hague
9.8 out of 10, Exceptional, (104 reviews)
"This condo has the most amazing views.of Lake George. We really enjoyed our stay and the calm/quiet area. Weather was a little cool so we were able to spend more time on the deck during the day. Vary spaciois rooms and 30 mins to Bolton Landing. Haugue is a cute little town with a beautiful landscape. We will be back."
United States
Alkan E.
$372 nightly
The price is $413
Sep 22 - Sep 23
Total with taxes and fees
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.
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

The Queensbury Hotel

The Queensbury Hotel

10/10 Excellent
"Loved everything about this hotel from the location in town, to the room, the lobby, the pool and the restaurant. Great stay."
Gary 1-night trip
Posted 5 hours ago
The Queensbury Hotel

Find out more about Chestertown

Chestertown Condo Rentals information

Number of reviews
104
Accommodation
8 Condo Rentals
Lowest Price
$413
Highest Price
$413

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 accommodations 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.

Explore a world of travel with Expedia