Photo by Julie Miller

Chestertown Holiday Rentals

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Chestertown holiday rentals

Egyptian cotton sheets, premium bedding, individually decorated
Trout House Village Resort

Cabin in Hague

Trout House Village Resort
3.0 star property
9.8 out of 10, Exceptional, (19)
"Great updated cabin. "
United States
Diane
The price is S$247
includes taxes & fees
24 Dec - 25 Dec
Trout House Village Resort
Interior
7 Mi to Glens Falls: Peaceful Retreat w/ Game Room

Cottage in Hudson Falls

7 Mi to Glens Falls: Peaceful Retreat w/ Game Room
3.0 star property
The price is S$733
includes taxes & fees
24 Dec - 25 Dec
7 Mi to Glens Falls: Peaceful Retreat w/ Game Room
Exterior
10 Mi To Gore Mountain: Home In Adirondack Park 5 Bedroom Home

Holiday Home in Olmstedville

10 Mi To Gore Mountain: Home In Adirondack Park 5 Bedroom Home
3.0 star property
The price is S$1,054
includes taxes & fees
11 Jan - 12 Jan, 2026
10 Mi To Gore Mountain: Home In Adirondack Park 5 Bedroom Home
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

The Queensbury Hotel

The Queensbury Hotel

10/10 Excellent
"As always, everything was perfect. "
Mike 1-night trip
Posted 5 hours ago
The Queensbury Hotel

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 56 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.