Photo by Julie Miller

Chestertown Vacation Rentals

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Tonight
Dec 28 - Dec 29
Tomorrow
Dec 29 - Dec 30
Next weekend
Jan 2 - Jan 4
In two weeks
Jan 9 - Jan 11

Our top choices for Chestertown vacation rentals

Living area
Trout House Village Resort

Cabin in Hague

Trout House Village Resort
3.0 star property
9.8 out of 10, Exceptional, (20)
"Great updated cabin. "
United States
Diane
The price is P8,789
P11,225 total
includes taxes & fees
Jan 4 - Jan 5, 2026
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 P8,636
P33,318 total
includes taxes & fees
Jan 1 - Jan 2, 2026
7 Mi to Glens Falls: Peaceful Retreat w/ Game Room
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

La Quinta Inn & Suites by Wyndham Lake George

La Quinta Inn & Suites by Wyndham Lake George

10/10 Excellent
"Room was spotless,staff was nice and helpful,very quiet we had a great relaxing time,room was spacious lots of room"
melissa 3-night trip
Posted 2 days ago
La Quinta Inn & Suites by Wyndham Lake George

Find out more about Chestertown

Search for holiday rentals in Chestertown on Expedia! You can easily find your home rentals, villas, holiday apartments in Chestertown using one of the methods below:

  • View our selection of featured holiday rentals in Chestertown
  • Use the map to find apartments and other holiday homes in the Chestertown neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chestertown while they last

Look no further and take a look at our great range of rental properties in Chestertown!

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 56 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.