AllTheRooms.

Chestertown, NY Vacation Rentals

  1. Vacation Rental Search
  2. United States of America
  3. New York
  4. Chestertown

Check prices for these upcoming dates

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.

More+

Price and Availability 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 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 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.
More+

The Weather in Chestertown

Rainy days
92° 50°
3
86° 42°
3
84° 31°
2
72° 28°
8
68° 3°
3
47° -6°
3
49° -20°
4
55° -18°
2
67° -5°
1
75° 19°
6
86° 37°
5
89° 40°
5
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
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 92 ˚F. The coolest month is December, when temperatures drop to -20 ˚F. The wettest month in Chestertown is March with 7.85 inches of rain, while the driest month is October with 1.22 inches of rain.

More+

What Expert Travelers Think

  • — As a mom of 5 kids who enjoy traveling, I love AllTheRooms! It is quick and easy to find the best deal on lodging that fits our family, in the area we'd like. AllTheRooms really does save you time, money, and hassle.

    Becky
    BeckyKid World Citizen
    Kid World Citizen

  • — I love AllTheRooms because it is not only local homes for renting, and not only hotels, but everything combined. When I am about to book a place to stay, I usually spend a couple of hours looking through both hotel sites and local home sites, comparing the prices and places.

    Alli Sims
    Alli SimsAlli Sims
    Visit Alli Sims

  • — I love how AllTheRooms shows a map with room price tags straight away when you search, it makes it so quick and easy to choose the right hotel, at the right price in the right location. Perfect for those with busy lifestyles! The AllTheRooms website is so user friendly. WiFi. Brilliant!

    Amanda Alston
    Amanda AlstonAmanda Alston
    Visit Amanda Alston

Destinations near Chestertown

  • New York14,756 Properties
  • Brooklyn9,498 Properties
  • Niagara Falls4,147 Properties
  • Queens2,688 Properties
  • Montauk1,493 Properties
  • Lake Placid1,461 Properties
  • Ithaca1,445 Properties
  • Sag Harbor842 Properties
  • Rochester811 Properties
  • Amagansett793 Properties
  • Lake George Village769 Properties
  • Hampton Bays712 Properties
  • Springs700 Properties
  • Southampton699 Properties
  • Ellicottville682 Properties
  • Albany592 Properties
  • Hunter585 Properties
  • Hudson561 Properties
  • Village of East Hampton543 Properties
  • Saugerties542 Properties
  • Woodstock520 Properties
  • Cooperstown510 Properties
  • Windham504 Properties
  • Chautauqua476 Properties
  • Lake George462 Properties
  • Ocean Beach450 Properties
  • Canandaigua443 Properties
  • Geneva433 Properties
  • Bridgehampton419 Properties
  • Saranac Lake403 Properties
  • Penn Yan382 Properties
  • Beacon380 Properties
  • Kingston370 Properties
  • Hammondsport357 Properties
  • Wilmington352 Properties
  • Noyack349 Properties
  • Cherry Grove338 Properties
  • Watkins Glen337 Properties
  • Yonkers332 Properties
  • Staten Island331 Properties
  • Syracuse329 Properties
  • Watermill318 Properties
  • Buffalo306 Properties
  • New Paltz294 Properties
  • East Quogue291 Properties
  • Alexandria Bay287 Properties
  • Greenport285 Properties
  • Southold274 Properties
  • Long Beach265 Properties
  • Bolton Landing265 Properties
  • Queensbury265 Properties
  • Warrensburg255 Properties
  • Wainscott246 Properties
  • Old Forge243 Properties
  • North Creek242 Properties
  • Cortland233 Properties
  • Shelter Island228 Properties
  • Binghamton227 Properties
  • Plattsburgh224 Properties
  • Auburn222 Properties
  • Catskill222 Properties
  • White Plains222 Properties
  • Rhinebeck220 Properties
  • Westhampton218 Properties
  • Westhampton Beach215 Properties
  • Poughkeepsie211 Properties
  • Skaneateles206 Properties
  • Trumansburg205 Properties
  • Pulaski198 Properties
  • Saratoga Springs195 Properties
  • Amherst183 Properties
  • Dundee171 Properties
  • Clayton165 Properties
  • Schroon Lake164 Properties
  • Quogue157 Properties
  • Newburgh141 Properties
  • Mount Vernon124 Properties
  • Fire Island119 Properties
  • Tupper Lake107 Properties
  • Diamond Point98 Properties
  • Fleischmanns91 Properties
  • Fishkill90 Properties
  • Millbrook67 Properties
  • Riverhead60 Properties
  • Ellenville59 Properties
  • Chatham56 Properties
  • City of Gloversville53 Properties
  • Port Jefferson40 Properties
  • Findley Lake38 Properties
  • Croton-on-Hudson38 Properties
  • Adirondack33 Properties
  • Sodus Point31 Properties
  • Washingtonville20 Properties
  • Star Lake11 Properties