Chestertown, NY Vacation Rentals

Our Favorite Vacation Rentals in Chestertown

  • Gore View Lodge
     Country House
    Booking.com
    From
    $325
  • Loon Lake Retreat with Private Dock
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $314
  • Contemporary ADK 5 Bedroom Chalet on Schroon
     Country House
    Booking.com
    From
    $344
  • LOON LAKE luxury Ski Gore,snowmobile,canoe,kayaks
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $444
  • Black Bear Cabin
    Excellent2br Cabin
    HolidayLettings
    From
    $215
  • The Treehouse at Atateka Point Lodge
    Excellent2br Treehouse
    HolidayLettings
    From
    $458
  • 2BR + Loft North Creek Cottage in the Adirondacks!
    Excellent2br Cottage
    HolidayLettings
    From
    $303
  • ADK Chalet Near Gore Mnt Adirondacks Minerva NY
    Excellent3br Chalet
    HolidayLettings
    From
    $186

Check prices for these upcoming dates

Chestertown Vacation Rentals with a Pool

  • Large Historic Adirondack House
    Good6br Home/Apartment
    Airbnb
    From
    $473
  • Adirondack Lodge steps from Gore Mt Ski Area
     6br Home/Apartment
    Airbnb
    From
    $1,045
  • Adirondack Birch Inspired Cabin
    ExcellentHome/Apartment
    Airbnb
    From
    $160
  • Adirondack Chalet
    Excellent3br Chalet
    Airbnb
    From
    $177

Chestertown Vacation Rentals with Wi-Fi

  • Lake George Adirondack stye house
    Excellent5br Home/Apartment
    Airbnb
    From
    $494
  • Meadow House
    Excellent5br Home/Apartment
    Airbnb
    From
    $266
  • Eagles Nest @ Loon Lake near Gore Mountain
    Excellent7br Home/Apartment
    Airbnb
    From
    $636
  • The Ramblewood. Family friendly!
    Good6br Home/Apartment
    Airbnb
    From
    $219

Chestertown Pet-Friendly Vacation Rentals

  • Gore Mountain ,North Creek, Lake George, Saratoga
    Good6br Home/Apartment
    Flipkey
    From
    $685
  • Adirondack Cabin in the Woods
    Excellent3br Home/Apartment
    Airbnb
    From
    $452
  • Mc Carthy Farm Wilderness
    Good4br Farm Stay
    Airbnb
    From
    $339
  • Autumn in the Adirondacks at On The Way Chalet
    Excellent3br Chalet
    Airbnb
    From
    $249

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 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.

The Weather in Chestertown

Rainy days
56°
5
55° 10°
4
57° -25°
2
66° -7°
2
51°
2
70° 17°
4
88° 32°
1
91° 41°
4
93° 45°
4
92° 51°
6
90° 37°
4
80° 22°
3
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
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 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.

What Expert Travelers Think

  • — 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
  • — 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
  • — Whenever I am making travel plans I always use comparison sites to find the best accommodation for us at the best price. Whether it be for hotel stays or private rentals AllTheRooms makes this so much easier and quicker as it brings all my searches into one place, with a great offering of options

    Sarah Pool
    Sarah PoolTammymum

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