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Chestertown Vacation Rentals

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Check prices for these dates

In two weeks
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Vacation Rentals in Chestertown

Fireplace
Lincoln Log Colony

Lincoln Log Colony

2.0 star property
Lake George
8.8 out of 10, Excellent, (10)
"This is a great property. Initially we rented a large “suite” but immediately upgraded to one of their adorable cabins just across from the playground and pool. The property has super nice and accommodating staff, plenty of parking and really nice families staying there; some are regulars for 20, 40 years! This is truly a family stay place and we were so happy to have found it. Now we’re planning to return year after year! Two beautiful Adirondack chairs on a quiet little stoop outside of each...
United States
Jill
Lincoln Log Colony
Interior
Waterfront Home on Lake George w/ Boat Dock!

Waterfront Home on Lake George w/ Boat Dock!

3.0 star property
Queensbury
Waterfront Home on Lake George w/ Boat Dock!
Living area
Trout House Village Resort

Trout House Village Resort

3.0 star property
Hague
9.8 out of 10, Exceptional, (17)
"Beautiful views and wonderful staff. Provides an atmosphere for activities and relaxation while being able to access anywhere on the lake."
United States
John
The price is P8,821
P11,265 total
includes taxes & fees
Nov 13 - Nov 14
Trout House Village Resort
Interior
9 Mi to Lake George Village: Home in Queensbury

9 Mi to Lake George Village: Home in Queensbury

3.0 star property
Queensbury
9 Mi to Lake George Village: Home in Queensbury
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

The Queensbury Hotel

The Queensbury Hotel

10/10 Excellent
"Always a pleasure to stay here. We stay here 1 or 2 weekends per year, but have never received a free breakfast. Not a complaint, just a statement. We highly recommend this hotel."
Daniel 1-night trip
Posted 1 day ago
The Queensbury Hotel

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 58 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.