Chestertown, NY 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 Index in Chestertown

Most expensive

Most availability

The most expensive month to stay in a vacation rental in Chestertown is in August, 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 April, 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

63º 13º

1.19

52º -21º

2.17

53º -3º

2.18

70º -5º

2.51

67º 2º

2.54

85º 25º

3.3

92º 31º

5.26

92º 38º

3.74

87º 48º

5.54

87º 41º

1.51

90º 34º

2.32

80º 27º

2.81

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Rainy days

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This climate histogram shows you the weather patterns in Chestertown. The warmest months in Chestertown are July and August, when temperatures reach 92 ˚F. The coolest month is January, when temperatures drop to -21 ˚F. The wettest month in Chestertown is June with 5.54 inches of rain, while the driest month is February with 1.19 inches of rain.

Vacation Rentals in Chestertown

Choose the perfect accommodation for your trip at AllTheRooms.com. We aggregate Airbnb, Homeaway, VRBO and more. Chestertown has 182 hotels, vacation rentals and other unique places to stay, with prices to suit budget travelers, luxury travelers and everything in between. For those trying to keep costs down, the lowest priced place to stay in Chestertown comes in at $40 per night. The average price of accommodation in is $275 per night.

If you want to stay connected during your trip, then you can choose from over 117 accommodations in Chestertown that have WiFi. We have 8 accommodations that come with a breakfast included. Driving to Chestertown? Then choose one of the 108 places to stay that comes with a parking spot included. 5 accommodations come with a pool or jacuzzi

If you're traveling with a furry friend, then be sure to choose one of the 33 pet-friendly accommodations available.

We combine a wide variety of Chestertown accommodations including vacation rentals, homestays, hostels and other unique places to stay into one easy search. We show results from more than 5 providers, including 56 places to stay from Airbnb, 35 accommodations from Homeaway and 22 places to stay from VRBO.

136 of our accommodations in Chestertown have been reviewed and rated. 78% are rated excellent or good. You can instantly book any of 49 places to stay right now.