
Vacation rentals in Chestertown
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Top-rated vacation rentals in Chestertown
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
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Popular amenities for Chestertown vacation rentals
Other great vacation rentals in Chestertown
Top guest favorite

Cabin in Brant Lake
5 out of 5 average rating, 9 reviewsForeverWild Cabin- River Access - LG - Firepit
Top guest favorite

Home in Warrensburg
4.97 out of 5 average rating, 98 reviewsLake George | Hot Tub | Firepit | Schroon Lake
Guest favorite

Home in Chestertown
5 out of 5 average rating, 10 reviewsSecluded and Cozy Townhome near Tripp Lake
Top guest favorite

Home in Chestertown
5 out of 5 average rating, 44 reviewsBlue Bay Retreat - Loon Lake Lakefront w/ Hot Tub
Top guest favorite

Home in Chestertown
5 out of 5 average rating, 34 reviewsThe Hayes Homestead
Top guest favorite

Home in Adirondack
5 out of 5 average rating, 91 reviewsWinter Wonderland/ Summer Solitude
Top guest favorite

Home in Chestertown
4.97 out of 5 average rating, 96 reviewsModern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
Guest favorite

Cabin in Brant Lake
4.98 out of 5 average rating, 40 reviewsCozy Chic 3 bedroom Cabin- Near lakes and hiking
Quick stats about vacation rentals in Chestertown
Total rentals
10 properties
Nightly prices starting at
$90 before taxes and fees
Total number of reviews
290 reviews
Wifi availability
10 properties include access to wifi
Popular amenities
Gym, BBQ grill, and Laptop-friendly workspace
Local attractions
Main Street Ice Cream Parlor, The Bullhouse, and Tops Friendly Markets
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- Saratoga Race Course
- Six Flags Great Escape Lodge & Indoor Water park
- Gore Mountain
- West Mountain Ski Resort
- Saratoga Spa State Park
- Lake George Expedition Park
- Pico Mountain Ski Resort
- Fort Ticonderoga
- Whiteface Mountain Ski Resort
- Dorset Field Club
- National Museum of Racing and Hall of Fame
- Northern Cross Vineyard
- Cozy Cottages & Otter Valley Winery
- Gooney Golf
- Willard Mountain
- Autumn Mountain Winery
- Lincoln Peak Vineyard
- Adirondack Extreme Adventure Course
- Family travel hub Tips and inspiration
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- Outdoor adventure Explore nature with the family
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- Kid-friendly state parks Check out these family-friendly hikes