Chestertown Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Chestertown vacation rentals

A landscaped garden with a fountain, flags, and a view of a body of water.

1. Walk to Schroon Lake! Studio w/ Shared Fire Pit

Walk to Schroon Lake! Studio w/ Shared Fire Pit
3.0 star property
Schroon Lake
10.0 out of 10, Exceptional, (2 reviews)
"Great place to stay near Ticonderoga NY"
United States
Adam
The price is P8,687
P10,686 total
includes taxes & fees
Nov 23 - Nov 24
Walk to Schroon Lake! Studio w/ Shared Fire Pit
A lakeside cabin with a wooden deck and a view of the lake.

2. Trout House Village Resort

Trout House Village Resort
3.0 star property
Hague
9.8 out of 10, Exceptional, (31 reviews)
"It was a great place, clean rooms, nice environment, cabins, family friendly, right on lake"
United States
Matthew
The price is P8,371
P10,866 total
includes taxes & fees
Dec 4 - Dec 5
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.
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Find vacation rentals that suit your style

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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 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.