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Chestertown, NY Vacation Rentals

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Our Favorite Vacation Rentals in Chestertown

  • Gore Ski House located in the heart of North Creek
    Gore Ski House located in the heart of North Creek
     5br Home/Apartment
    HolidayLettingsFrom $458
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  • The Brampton
    The Brampton
    Excellent7br Home/Apartment
    HolidayLettingsFrom $2573
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  • Little Moose Bungalow in the Adirondacks
    Little Moose Bungalow in the Adirondacks
    Okay3br Bungalow
    HolidayLettingsFrom $172
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  • Cozy Cottage on 6 acres close to Gore Mountain
    Cozy Cottage on 6 acres close to Gore Mountain
     2br Home/Apartment
    HolidayLettingsFrom $315
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  • Gore Mountain ,North Creek, Lake George, Saratoga
    Gore Mountain ,North Creek, Lake George, Saratoga
    Good6br Home/Apartment
    FlipkeyFrom $685
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  • Hand-Crafted Cottage near Gore Mountain
    Hand-Crafted Cottage near Gore Mountain
     2br Cottage
    HolidayLettingsFrom $206
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  • NEW LISTING! House near the lake - full kitchen, washer/dryer, quiet location!
    NEW LISTING! House near the lake - full kitchen, washer/dryer, quiet location!
     2br Home/Apartment
    HolidayLettingsFrom $230
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  • 2BR + Loft North Creek Cottage in the Adirondacks!
    2BR + Loft North Creek Cottage in the Adirondacks!
     2br Cottage
    HolidayLettingsFrom $266
    View Deal
See all 241 deals in Chestertown

Chestertown Vacation Rentals with a Pool

  • Adirondack Mountain Haus
    Adirondack Mountain Haus
    Excellent3br Home/Apartment
    AirbnbFrom $338
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  • WOODSMAN'S PARADISE!
    WOODSMAN'S PARADISE!
     3br Home/Apartment
    AirbnbFrom $565
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  • 10 ACRES OF ADIRONDACK RUSTIC CHARM
    10 ACRES OF ADIRONDACK RUSTIC CHARM
    Okay3br Other
    AirbnbFrom $622
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See all deals in Chestertown with a pool

Chestertown Vacation Rentals with Wi-Fi

  • NEW LISTING! Lakefront cottage w/ full kitchen, sandy beach, dock and swim float
    NEW LISTING! Lakefront cottage w/ full kitchen, sandy beach, dock and swim float
     3br Home/Apartment
    AirbnbFrom $319
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  • NEW LISTING! Lakefront, 3-level house on a cove with beach & large dock
    NEW LISTING! Lakefront, 3-level house on a cove with beach & large dock
     5br Home/Apartment
    AirbnbFrom $653
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  • Large Apartment Rental in Chestertown
    Large Apartment Rental in Chestertown
    Excellent4br Home/Apartment
    AirbnbFrom $904
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  • Tree Tops
    Tree Tops
    Good6br Other
    AirbnbFrom $593
    View Deal
See all deals in Chestertown with WiFis

Chestertown Pet-Friendly Vacation Rentals

  • NEW LISTING! Dog-friendly cabin with lakefront location, 20' dock, smart TV
    NEW LISTING! Dog-friendly cabin with lakefront location, 20' dock, smart TV
     3br Home/Apartment
    AirbnbFrom $297
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  • NEW LISTING! Dog-friendly, lakefront house with 2 living areas, beach nearby
    NEW LISTING! Dog-friendly, lakefront house with 2 living areas, beach nearby
     4br Home/Apartment
    AirbnbFrom $421
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  • Hemlock Camp
    Hemlock Camp
     Home/Apartment
    AirbnbFrom $102
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  • Gore Mtn Chalet (5 minutes from skiing, & hiking!)
    Gore Mtn Chalet (5 minutes from skiing, & hiking!)
    Excellent5br Chalet
    AirbnbFrom $450
    View Deal
See all deals in Chestertown that allow pets

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
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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 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

93º 45º
4.14
92º 51º
5.55
90º 37º
3.65
80º 22º
3.11
56º 3º
5.24
55º 10º
4.25
57º -25º
1.74
66º -7º
2.27
51º 5º
1.73
70º 17º
3.7
88º 32º
1.25
91º 41º
3.69
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 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

Destinations near Chestertown