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Chestertown, NY Vacation Rentals

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Our Favorite Vacation Rentals in Chestertown

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Chestertown Vacation Rentals with Pool

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Chestertown Vacation Rentals with Wi-Fi

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Chestertown Pet Friendly Vacation Rentals

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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

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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

53º -3º
2.18
70º -5º
2.51
67º 2º
2.54
85º 25º
3.3
92º 31º
5.26
53º -3º
2.18
87º 48º
5.54
87º 41º
1.51
90º 34º
2.32
80º 27º
2.81
63º 13º
1.19
52º -21º
2.17
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May
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Sep
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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 August and April, when temperatures reach 92 ˚F. The coolest month is December, when temperatures drop to -21 ˚F. The wettest month in Chestertown is July with 5.54 inches of rain, while the driest month is November with 1.19 inches of rain.

Vacation Rentals in Chestertown

Browse accommodations from all the best providers including Airbnb, Homeaway, VRBO and more at AllTheRooms.com. Chestertown has 212 hotels, vacation rentals and other unique places to stay, with prices to suit budget travelers, luxury travelers and everything in between. For those traveling on a budget, the cheapest place to stay in Chestertown is available at $40 per night. On average, a place to stay in Chestertown will cost you $285 per night.

If you need an internet connection during your stay in Chestertown, then you can choose from over 115 places to stay that provide WiFi internet. We have 9 accommodations that come with a breakfast included. Driving to Chestertown? Then choose one of the 106 places to stay that comes with a parking spot included. 5 accommodations come with a pool or jacuzzi

Those traveling with a dog, cat or some other animal can stay in one of 33 accommodations that are designated as pet-friendly.

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 58 places to stay from Airbnb, 30 accommodations from Homeaway and 21 places to stay from VRBO.

137 accommodations in Chestertown have been reviewed: 78% are rated excellent or good. You can instantly book any of 79 places to stay right now.

Destinations near Chestertown

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