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Chestertown, NY Vacation Rentals

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  2. United States of America
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  4. Chestertown

Our Favorite Vacation Rentals in Chestertown

  • Brown's Beach at Schroon Lake
     Country House
    Booking.com
    From
    $507
  • Gorgeous and spacious beachfront condo with shared pool and beach access
     3br Home/Apartment
    HolidayLettings
    From
    $187
  • Contemporary ADK 5 Bedroom Chalet on Schroon
     Country House
    Booking.com
    From
    $512
  • Family-friendly coastal condo with shared pool, hot tub and easy beach access!
     4br Home/Apartment
    HolidayLettings
    From
    $277
  • LOON LAKE luxury Ski Gore,snowmobile,canoe,kayaks
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $444
  • Black Bear Cabin
    Excellent2br Cabin
    HolidayLettings
    From
    $215
  • Friends Lake- Quaint and New
    Good2br Cottage
    HolidayLettings
    From
    $285
  • The Treehouse at Atateka Point Lodge
    Excellent2br Treehouse
    HolidayLettings
    From
    $429
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Check prices for these upcoming dates

Chestertown Vacation Rentals with a Pool

  • Gore Mnt. Ski Resort 62 Bldg. H
     3br Home/Apartment
    Airbnb
    From
    $763
  • Gore Mnt. Ski Resort 10 Bldg. M
     Home/Apartment
    Airbnb
    From
    $579
  • Gore Mnt. Ski Resort- 60 Bldg. H
     2br Home/Apartment
    Airbnb
    From
    $672
  • Gore Mnt. Ski Resort 24 Bldg. C
     3br Home/Apartment
    Airbnb
    From
    $763
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Chestertown Vacation Rentals with Wi-Fi

  • The Cabin at Loch Loon
    Excellent4br Home/Apartment
    Airbnb
    From
    $370
  • The Green Cabin
     3br Home/Apartment
    Airbnb
    From
    $367
  • Adirondack Cabin in the Woods
    Excellent3br Home/Apartment
    Airbnb
    From
    $424
  • Cozy Adirondack Apartment
    ExcellentHome/Apartment
    Airbnb
    From
    $112
Show all

Chestertown Pet-Friendly Vacation Rentals

  • Blue Ridge cabin w/tri-state views, theater room & multiple decks
     3br Home/Apartment
    HolidayLettings
    From
    $791
  • The Adirondack Getaway
    Excellent4br Home/Apartment
    HolidayLettings
    From
    $172
  • Gore Mountain ,North Creek, Lake George, Saratoga
    Good6br Home/Apartment
    Flipkey
    From
    $685
  • PoshPrimitive Adirondack FawnTent
    ExcellentHome/Apartment
    Airbnb
    From
    $446
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
49° -20°
4
55° -18°
2
67° -5°
1
75° 19°
6
86° 37°
5
89° 40°
5
92° 50°
3
86° 42°
3
84° 31°
2
72° 28°
8
68° 3°
3
47° -6°
3
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
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.

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What Expert Travelers Think

  • — Site is easy to use; clean, laid out well, good colors and branding, fun logo and title that connects to the purpose of the brand. The blog, vacation destinations, and rental destinations is a great feature and really make the brand stand apart from other sites!

    Laurelle McVicker
    Laurelle McVickerLaurelle McVicker
    Laurelle McVicker

  • — My favorite thing about AllTheRooms is that it combines both rentals and hotels available so you can see an entire view of what is available in a certain area. I was able to see listings on AllTheRooms that I never even saw on other travel sites!

    Daniella Flores
    Daniella FloresILIKETODABBLE
    Visit ILIKETODABBLE

  • — The great thing about AllTheRooms is their ability to cover all bases. If you are travelling solo, with a partner, friends or even a larger family. There is something there for everyone and that is a hugely powerful tool that I believe it boasts moreso than competitors.

    Max Hobbs
    Max HobbsLTL Mandarin School
    LTL Mandarin School

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