We use cookies to provide you with the best browsing experience. The data collected by cookies is used to optimise the website for our users and deliver an appropriate service and relevant information to you. By using our site we assume you’re aware and agree to use the cookies for this purpose.

Destination Photo

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
, , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0 , , , , , , , , , , , , , , , , , , , , , , Jan , Feb , Mar , Apr , May , Jun , Jul , Aug , Sep , Oct , Nov , Dec 1 , 0.9 , 0.8 , 0.7 , 0.6 , 0.5 , 0.4 , 0.3 , 0.2 , 0.1 , 0
Powered by:
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

51º
1.73
70º 17º
3.7
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
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Feb
Rainy days
This climate histogram shows you the weather patterns in Chestertown. The warmest months in Chestertown are June and May, when temperatures reach 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

Choose the perfect accommodation for your trip at AllTheRooms.com. We aggregate Airbnb, Homeaway, VRBO and more. Chestertown has 222 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 $25 per night. The average price of accommodation in is $286 per night.

Those looking to get some work done during their trip to Chestertown can pick from 136 places to stay that provide WiFi. We have 11 accommodations that come with a breakfast included. You can keep up with your workout regime by staying at one of 3 accommodations that provide gym facilities. Driving to Chestertown? Then choose one of the 126 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 38 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 78 places to stay from Airbnb, 32 accommodations from Homeaway and 20 places to stay from VRBO.

140 of our accommodations in Chestertown have been reviewed and rated. 67% are rated excellent or good. 87 places to stay in are instantly bookable.