Photo by Julie Miller

Chestertown Holiday Rentals

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Check prices for these dates

Tonight
5 Nov - 6 Nov
Tomorrow
6 Nov - 7 Nov
This weekend
7 Nov - 9 Nov
Next weekend
14 Nov - 16 Nov

Holiday Rentals in Chestertown

Fireplace
Lincoln Log Colony
Lincoln Log Colony
2.0 star property
8.8 out of 10, Excellent, (10)
"This is a great property. Initially we rented a large “suite” but immediately upgraded to one of their adorable cabins just across from the playground and pool. The property has super nice and accommodating staff, plenty of parking and really nice families staying there; some are regulars for 20, 40 years! This is truly a family stay place and we were so happy to have found it. Now we’re planning to return year after year! Two beautiful Adirondack chairs on a quiet little stoop outside of each...
United States
Jill
Lincoln Log Colony
Interior
Waterfront Home on Lake George w/ Boat Dock!
Waterfront Home on Lake George w/ Boat Dock!
3.0 star property
Waterfront Home on Lake George w/ Boat Dock!
Living area
Trout House Village Resort
Trout House Village Resort
3.0 star property
9.8 out of 10, Exceptional, (17)
"Beautiful views and wonderful staff. Provides an atmosphere for activities and relaxation while being able to access anywhere on the lake."
United States
John
The price is S$249
includes taxes & fees
6 Nov - 7 Nov
Trout House Village Resort
Interior
9 Mi to Lake George Village: Home in Queensbury
9 Mi to Lake George Village: Home in Queensbury
3.0 star property
9 Mi to Lake George Village: Home in Queensbury
In-room dining
The Elms Waterfront Cottages
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. "
United States
Amanda
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

The Queensbury Hotel

The Queensbury Hotel

10/10 Excellent
"Very clean hotel and very welcoming and nice staff."
Zhanna 2-night trip
Posted 2 days 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 58 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.