Photo by Julie Miller

Chestertown Holiday Rentals

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Check prices for these dates

In two weeks
3 Oct - 5 Oct
In two months
14 Nov - 16 Nov
In three months
12 Dec - 14 Dec
In four months
9 Jan - 11 Jan

Holiday Rentals in Chestertown

Our top choices for Chestertown holiday rentals

Trout House Village Resort
Living area

Trout House Village Resort

3.0 star property
9.8 out of 10, Exceptional, (13)
"Very friendly owner and beautiful views"
The price is S$244
includes taxes & fees
21 Sept - 22 Sept
Trout House Village Resort
Waterfront Home on Lake George w/ Boat Dock!
Interior

Waterfront Home on Lake George w/ Boat Dock!

3.0 star property
Waterfront Home on Lake George w/ Boat Dock!
Lake George Escape - Campground
2 bedrooms, WiFi

Lake George Escape - Campground

2.0 star property
8.4 out of 10, Very good, (166)
"Nice place to staying "
Lake George Escape - Campground
The Elms Waterfront Cottages
In-room dining

The Elms Waterfront Cottages

2.5 star property
8.4 out of 10, Very good, (16)
"We were treated like royalty here at the Elms. The owner, Chandler and his staff, go above and beyond. What a beautiful escape. We will most definitely return. "
The price is S$529
includes taxes & fees
21 Sept - 22 Sept
The Elms Waterfront Cottages
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

Baymont by Wyndham Queensbury / Lake George

Baymont by Wyndham Queensbury / Lake George

10/10 Excellent
"Good"
Colleen 4-night trip
Posted 2 days ago
Baymont by Wyndham Queensbury / Lake George

Frequently asked questions

Can I find holiday rentals in Chestertown?

Yes, there are holiday rentals close to the most popular sights in Chestertown, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the lakeside in Chestertown. Make sure you have time to check out the coffee shops and forests during your trip.

How many holiday rentals will I find in Chestertown?

With 60 Expedia holiday rentals, you're guaranteed to find just the right place for your Chestertown stay.

What’s there to see and do in Chestertown?

Loon Lake Beach and Friends Lake are a couple of lovely local spots to get outside and enjoy nature. Loon Lake and Hudson River are other places to visit while you're in town.

What’s a holiday rental in Chestertown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chestertown. Holiday rentals provide amenities like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for family trips or small group gatherings.