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Chestertown, NY Vacation Rentals

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  4. Chestertown

Our Favorite Vacation Rentals in Chestertown

  • Adirondack Contemporary
     Country House
    Booking.com
    From
    $371
  • Loon Lake Retreat with Private Dock
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $308
  • Tentrr - Camp Gore on the Hudson
     Country House
    Booking.com
    From
    $146
  • LOON LAKE luxury Ski Gore,snowmobile,canoe,kayaks
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $444
  • Tentrr - Pucker Ridge Farm
     Country House
    Booking.com
    From
    $140
  • Lakefront North Creek Cabin w/Sauna, Dock & Kayaks
     3br Cabin
    HolidayLettings
    From
    $543
  • Contemporary ADK 5 Bedroom Chalet on Schroon
     Country House
    Booking.com
    From
    $459
  • Black Bear Cabin
    Excellent2br Cabin
    HolidayLettings
    From
    $215
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Check prices for these upcoming dates

Chestertown Vacation Rentals with a Pool

  • Large Historic Adirondack House
    Good6br Home/Apartment
    Airbnb
    From
    $479
  • Adirondack Birch Inspired Cabin
    ExcellentHome/Apartment
    Airbnb
    From
    $160
  • Adirondack Chalet
    Excellent3br Chalet
    Airbnb
    From
    $206
  • Adirondack Mountain Haus
    Excellent3br Home/Apartment
    Airbnb
    From
    $266
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Chestertown Vacation Rentals with Wi-Fi

  • Meadow House
    Excellent5br Home/Apartment
    Airbnb
    From
    $266
  • Eagles Nest @ Loon Lake near Gore Mountain
    Excellent7br Home/Apartment
    Airbnb
    From
    $593
  • Behan Cottage at Loon Lake
    Excellent4br Home/Apartment
    Airbnb
    From
    $396
  • The Ramblewood. Family friendly!
    Good6br Home/Apartment
    Airbnb
    From
    $247
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Chestertown Pet-Friendly Vacation Rentals

  • Friends Lake- Quaint and New
    Good2br Cottage
    HolidayLettings
    From
    $285
  • Gore Mountain ,North Creek, Lake George, Saratoga
    Good6br Home/Apartment
    Flipkey
    From
    $685
  • Tentrr - Pucker Ridge Farm
     Home/Apartment
    HolidayLettings
    From
    $160
  • Rustic Tiny Cabin
    ExcellentCabin
    Airbnb
    From
    $89
Show all

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.

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Price and Availability in Chestertown

Most expensive
Most availability
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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.
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The Weather in Chestertown

Rainy days
90 º37
4
80 º22
3
56 º3
5
55 º10
4
57 º-25
2
66 º-7
2
51 º5
2
70 º17
4
88 º32
1
91 º41
4
93 º45
4
92 º51
6
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
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 December, when temperatures drop to -25 ˚F. The wettest month in Chestertown is May with 5.55 inches of rain, while the driest month is August with 1.25 inches of rain.

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