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

Search Chestertown Condo Rentals

  • 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
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 AU$584
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.
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

Baymont by Wyndham Queensbury / Lake George

Baymont by Wyndham Queensbury / Lake George

8/10 Good
"Breakfast wasn’t very good"
Robert 1-night trip
Posted 2 hours ago
Baymont by Wyndham Queensbury / Lake George

Find out more about Chestertown

Chestertown Condo Rentals information

Number of reviews
106
Accommodation
8 Condo Rentals
Lowest Price
AU$584
Highest Price
AU$584

Frequently asked questions

What is there to do in Chestertown near my condo?
Chestertown has enough activities and sights to keep you on the hop for weeks (or months!), starting with Loon Lake Beach. Natural Stone Bridge and Caves, Loon Lake and Friends Lake are other well-known attractions. If you're sticking around a while, Avalanche Lake and Tripp Pond are nice final touches to your itinerary.