Photo by Julie Miller

Chestertown Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Vacation Rentals in Chestertown

Lake George Escape - Campground

2.0 star property
8.4 out of 10, Very Good, (164)
"Nice place to staying "
Lake George Escape - Campground

Waterfront Home on Lake George w/ Boat Dock!

3.0 star property
Waterfront Home on Lake George w/ Boat Dock!

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 NT$9,244
NT$10,261 total
includes taxes & fees
Aug 24 - Aug 25
The Elms Waterfront Cottages

Trout House Village Resort

3.0 star property
9.8 out of 10, Exceptional, (12)
"Absolutely wonderful place and super friendly staff "
The price is NT$4,271
NT$5,487 total
includes taxes & fees
Sep 2 - Sep 3
Trout House Village Resort
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chestertown Hotel Reviews

Frequently asked questions

Can I find vacation rentals in Chestertown?

Yes, we give you a choice of vacation rentals near well known points of interest in Chestertown, or you can choose a more remote option if you want a relaxing place to stay. Nature enthusiasts will enjoy the lakeside in Chestertown. Make sure you have time to check out the coffeehouses and forests during your trip.

How many vacation rentals will I find in Chestertown?

With 62 Expedia vacation rentals, you're sure 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 vacation rental in Chestertown like?

Vacation rentals are private properties you can book for a couple of days or more in Chestertown. Vacation rentals provide amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a small group gathering.