Photo by Julie Miller

Chestertown Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Chestertown

Other types of properties in Chestertown you may be interested in

Water park
Six Flags Lodge & Indoor Waterpark
3.5 star property
7.6 out of 10, Good, (1000)
"Great getaway for the kids. They loved it."
The price is S$344
includes taxes & fees
23 May - 24 May
Six Flags Lodge & Indoor Waterpark
Indoor pool
La Quinta Inn & Suites by Wyndham Lake George
2.0 star property
9.0 out of 10, Wonderful, (1220)
"Hotel was very clean and modern Breakfast was buffet and it was as good as that can be , got to love them waffles , Person in charge of breakfast was well organized and kept it all moving Indoor Pool is nice , particularly for kids "
The price is S$139
includes taxes & fees
2 Jun - 3 Jun
La Quinta Inn & Suites by Wyndham Lake George
Lobby
The Queensbury Hotel
3.0 star property
9.2 out of 10, Wonderful, (1113)
"We had a lovely meal in one of the 2 restaurants. Our room was on the top floor and was very quiet. There wasn't much room on the left side of bed -- very close to the wall -- I had to scoot toward the foot of the bed in order to clear the small nightstand. The VIP benefit (discount on food/drink) was not properly applied to our bill despite our following the letter given to us at check-in. The clerk at the desk on the morning we checked out said he would take care of the credit and email me a...
The price is S$193
includes taxes & fees
23 May - 24 May
The Queensbury Hotel
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.

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.

Recent reviews of Chestertown properties
Expedia verified reviews