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Chestertown, NY Vacation Rentals

Our Favorite Vacation Rentals in Chestertown

Chestertown Vacation Rentals with a Pool

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Chestertown Pet-Friendly Vacation Rentals

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

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
88º 32º
1.25
91º 41º
3.69
Jul
Aug
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Dec
Jan
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May
Jun
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.

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