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Chestertown, NY Vacation Rentals

Our Favorite Vacation Rentals in Chestertown

See all 221 vacation rentals in Chestertown

Chestertown Vacation Rentals with a Pool

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Chestertown Vacation Rentals with Wi-Fi

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Chestertown Pet-Friendly Vacation Rentals

See all vacation rentals in Chestertown that allow pets

Chestertown Travel Guide

A tiny hamlet in Warren County, Chestertown offers plenty of fun for visitors, despite it’s tiny size. Nearby are other Adirondack destinations that mean Chestertown is a popular stopping-off point.

Things to Do in Chestertown

Both Friends Lake and Loon Lake are great for swimming, cruising the waters on a boat, or hanging out on the shores with a picnic. The lakes are also particularly beautiful at sunset.

Horseback riding is a popular pastime here too, with a local family-run ranch hosting tours to explore the Adirondacks through miles of trails, forests and fields. Elsewhere, seasonal fun can be had in the nearby Dynamite Hill Park area with acres of land pefect for hiking or skiing and ice skating in winter.

After a long day exploring, check out the farmers' markets and local restaurants to savor local produce and ingredients.

Best Time to Visit Chestertown

Chestertown is best visited in the late spring and early summer for ideal weather to be outdoors.

Price and Availability in Chestertown

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The most expensive month to stay in a vacation rental in Chestertown is in December, while the cheapest month is in April. The most popular time to book a vacation rental in Chestertown is in the high season in July. Chestertown has its low season in November, when less people are visiting and the vacation home occupancy rate drops.
The cheapest day to stay at a vacation rental in Chestertown tends to be Tuesday, while the most expensive day tends to be Saturday. Vacation homes in Chestertown tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.

The Weather in Chestertown

88º 32º
1.25
91º 41º
3.69
93º 45º
4.14
92º 51º
5.55
90º 37º
3.65
80º 22º
3.11
56º
5.24
55º 10º
4.25
57º -25º
1.74
66º -7º
2.27
51º
1.73
70º 17º
3.7
May
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Rainy days
This climate histogram shows you the weather patterns in Chestertown. The hottest month in Chestertown is June, when temperatures peak at 93 ˚F. The coolest month is January, when temperatures drop to -25 ˚F. The wettest month in Chestertown is August with 5.55 inches of rain, while the driest month is May with 1.25 inches of rain.

What Expert Travelers Think

Vacation Rentals in Chestertown

Browse accommodations from all your favorite providers including Airbnb, Homeaway, VRBO and many more at AllTheRooms.com. We have 221 vacation rentals, hotels and other accommodation types in Chestertown ranging from low-cost options to luxury places to stay. A trip to Chestertown can be budget-friendly - the cheapest price accommodation is available at $40 a night. In general, a place to stay in Chestertown will cost you $287 per night.

Those needing to get some work done during their trip to Chestertown can pick from 133 places to stay that include WiFi. We have 9 accommodations that come with breakfast included. If you are driving to Chestertown, you'll want to pick from 122 places to stay that provide parking.

If you're traveling with your best friend, then make sure to choose one of the 40 pet-friendly accommodations available.

We compare vacation rentals, hotels and other unique accommodation types from loads of providers in Chestertown, including 75 places to stay from Airbnb, 32 accommodations from Homeaway and 19 places to stay from VRBO

137 of the accommodations in Chestertown have been reviewed by previous guests. They rated 68% as great. 76 places to stay in are instantly bookable.

Destinations near Chestertown