Photo by Julie Miller

Chestertown Holiday Rentals

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Check prices for these dates

Tonight
1 Jul - 2 Jul
Tomorrow
2 Jul - 3 Jul
This weekend
4 Jul - 6 Jul
Next weekend
11 Jul - 13 Jul

Holiday Rentals in Chestertown

Lake George Escape - Campground
Exterior

Lake George Escape - Campground

2.0 star property
8.4 out of 10, Very good, (160)
"Had an amazing stay. The people at the front desk especially sylvia were so kind amd friendly. Everyone was so helpful. The cabins are so clean and well stocked. The grounds are beautiful too"
Lake George Escape - Campground
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!
Trout House Village Resort
Living area

Trout House Village Resort

3.0 star property
10.0 out of 10, Exceptional, (11)
"Absolutely wonderful place and super friendly staff "
The price is S$385
includes taxes & fees
5 Jul - 6 Jul
Trout House Village Resort
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$511
includes taxes & fees
2 Jul - 3 Jul
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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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?

Friends Lake and Loon Lake are a couple of lovely local spots to get outside and enjoy nature. Hudson River and Loon Lake Beach 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.