Chestertown, New York

Vacation Rentals in Chestertown, New York

Discover 47 vacation rental properties in Chestertown. From 1 to 7 bedrooms. Average $244/night. 100% have pools.

47 verified listings Book securely on VRBO Prices updated March 2026

47 properties available

Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George

Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George

3 beds 2 baths
PoolA/CWiFiBalcony
$251/night
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#4 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!

#4 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!

2 beds 2 baths
PoolA/CWiFiBalcony
$140/night
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A beautiful lake view cabin on Friends Lake

A beautiful lake view cabin on Friends Lake

2 beds
PoolA/CWiFiBalcony
$165/night
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Lakefront cabin with beautiful views, lake and beach access

Lakefront cabin with beautiful views, lake and beach access

1 bed 2 baths
PoolA/CWiFiBalcony
$131/night
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Log Haven, Pool/AC/Fireplace, Cozy Adirondack Mountains Cabin Steps to Loon Lake

Log Haven, Pool/AC/Fireplace, Cozy Adirondack Mountains Cabin Steps to Loon Lake

2 beds 1 bath
PoolA/CWiFiBalcony
$262/night
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Adirondack style condo on Tripp lake and near Gore Mt. Ski resort

Adirondack style condo on Tripp lake and near Gore Mt. Ski resort

1 bed 2 baths
PoolA/CWiFiBalcony
$135/night
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Beautiful lakeview cottage on Friends Lake

Beautiful lakeview cottage on Friends Lake

2 beds 1 bath
PoolA/CWiFiBalcony
$165/night
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TRIPP LAKE RETREAT sleeps 7 and is a great place to make Adirondack memories!

TRIPP LAKE RETREAT sleeps 7 and is a great place to make Adirondack memories!

3 beds 2 baths
PoolA/CWiFiBalcony
$325/night
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#5 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!

#5 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!

4 beds 1 bath
PoolA/CWiFiBalcony
$170/night
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Private Waterfront House on Loon Lake with Amazing Views by Lake George and Gore

Private Waterfront House on Loon Lake with Amazing Views by Lake George and Gore

3 beds 1 bath
PoolA/CWiFiBalcony
$425/night
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Lily Pad North at Loon Lake near Gore Mountain

Lily Pad North at Loon Lake near Gore Mountain

2 beds 1 bath
PoolA/CWiFiBalcony
$113/night
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Tree-lined dog-friendly cottage with wrap-around deck, grill, & gas fireplace

Tree-lined dog-friendly cottage with wrap-around deck, grill, & gas fireplace

3 beds 1 bath
PoolA/CWiFiBalcony
$166/night
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Lily Pad South at Loon Lake near Gore Mountain

Lily Pad South at Loon Lake near Gore Mountain

2 beds 1 bath
PoolA/CWiFiBalcony
$102/night
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Adirondack Base Camp by Loon Lake and Gore Mt.!

Adirondack Base Camp by Loon Lake and Gore Mt.!

2 beds 1 bath
PoolA/CWiFiBalcony
$164/night
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Deer Crossing, A Beautiful Loon Lake Family Cabin in the Adirondack Mountains

Deer Crossing, A Beautiful Loon Lake Family Cabin in the Adirondack Mountains

1 bed
PoolA/CWiFiBalcony
$163/night
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Welcome home!

Welcome home!

3 beds 2 baths
PoolA/CWiFiBalcony
$301/night
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Perfect Home Base for your Adirondack Adventure

Perfect Home Base for your Adirondack Adventure

3 beds 3 baths
PoolA/CWiFiBalcony
$262/night
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Lakefront cabin with beautiful loft, game room, views, private dock

Lakefront cabin with beautiful loft, game room, views, private dock

5 beds 3 baths
PoolA/CWiFiBalcony
$206/night
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Beautiful waterfront home with hot tub & firepit - right on the river's edge

Beautiful waterfront home with hot tub & firepit - right on the river's edge

3 beds 2 baths
PoolA/CWiFiBalcony
$309/night
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Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing

Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing

3 beds 2 baths
PoolA/CWiFiBalcony
$321/night
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Year round Log Cabin on 2 acres on Loon Lake. Minutes from Gore

Year round Log Cabin on 2 acres on Loon Lake. Minutes from Gore

5 beds 3 baths
PoolA/CWiFiBalcony
$349/night
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Classic riverfront cottage w/ beautiful water views, WiFi, & screened porches

Classic riverfront cottage w/ beautiful water views, WiFi, & screened porches

2 beds 1 bath
PoolA/CWiFiBalcony
$152/night
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Spacious country home with large yard minutes from to

Spacious country home with large yard minutes from to

3 beds 2 baths
PoolA/CWiFiBalcony
$226/night
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Rustic Adirondacks Home w/ Hot Tub & Lake Access!

Rustic Adirondacks Home w/ Hot Tub & Lake Access!

3 beds 1 bath
PoolA/CWiFiBalcony
$323/night
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Hide-A-Way Cabin, Pool & AC, Authetic Adirondack Cabin Steps from Loon Lake

Hide-A-Way Cabin, Pool & AC, Authetic Adirondack Cabin Steps from Loon Lake

1 bed 1 bath
PoolA/CWiFiBalcony
$215/night
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Eagles Nest @ Loon Lake near Gore Mountain

Eagles Nest @ Loon Lake near Gore Mountain

7 beds 4 baths
PoolA/CWiFiBalcony
$464/night
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2-Story Home w/Pond Views, Gas Grill, Fire Pit, Washer/Dryer, and Partial A/C

2-Story Home w/Pond Views, Gas Grill, Fire Pit, Washer/Dryer, and Partial A/C

3 beds 1 bath
PoolA/CWiFiBalcony
$199/night
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Loon Lake Log Cabin with canoe and kayaks, fire pit, and game room!

Loon Lake Log Cabin with canoe and kayaks, fire pit, and game room!

4 beds 1 bath
PoolA/CWiFiBalcony
$263/night
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Cozy Lakeside Property with dock, kayaks and paddle boards

Cozy Lakeside Property with dock, kayaks and paddle boards

4 beds 2 baths
PoolA/CWiFiBalcony
$431/night
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5 Bd, 2 BA Home Overlooking a Thoroughbred Horse Farm

5 Bd, 2 BA Home Overlooking a Thoroughbred Horse Farm

5 beds 2 baths
PoolA/CWiFiBalcony
$124/night
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Chipmunk Cabin, Beautiful hand carved King Bed, Full Kitchen, plus AC! sleep 2

Chipmunk Cabin, Beautiful hand carved King Bed, Full Kitchen, plus AC! sleep 2

1 bed 1 bath
PoolA/CWiFiBalcony
$163/night
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#2 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!

#2 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!

3 beds 2 baths
PoolA/CWiFiBalcony
$137/night
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Tall Pines On Loon Lake

Tall Pines On Loon Lake

4 beds 1 bath
PoolA/CWiFiBalcony
$337/night
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The Roost, a lakefront 4 season home in the Adirondack Mountains

The Roost, a lakefront 4 season home in the Adirondack Mountains

4 beds 3 baths
PoolA/CWiFiBalcony
$370/night
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Peaceful Lakeside Retreat with Private Beach

Peaceful Lakeside Retreat with Private Beach

2 beds 1 bath
PoolA/CWiFiBalcony
$272/night
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Private Adirondack lakefront Cottage on Loon Lake

Private Adirondack lakefront Cottage on Loon Lake

2 beds 1 bath
PoolA/CWiFiBalcony
$175/night
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#6 Lakeview @Birchwood Cottages at Loon Lake. Family Friendly Waterfront

#6 Lakeview @Birchwood Cottages at Loon Lake. Family Friendly Waterfront

4 beds 1 bath
PoolA/CWiFiBalcony
$170/night
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Secluded and Cozy Townhome near Tripp Lake

Secluded and Cozy Townhome near Tripp Lake

3 beds 3 baths
PoolA/CWiFiBalcony
$154/night
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Dog-friendly cabin with lakefront location, 20' dock, smart TV

Dog-friendly cabin with lakefront location, 20' dock, smart TV

3 beds 1 bath
PoolA/CWiFiBalcony
$161/night
View Details → Book on VRBO
Lakefront Cottage with Screened Gazebo, Dock, and Two Acres of Space

Lakefront Cottage with Screened Gazebo, Dock, and Two Acres of Space

3 beds 1 bath
PoolA/CWiFiBalcony
$175/night
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Adirondack JEM - 20 Minutes to Lake George or Gore Mountain for Four Season Fun!

Adirondack JEM - 20 Minutes to Lake George or Gore Mountain for Four Season Fun!

2 beds 2 baths
PoolA/CWiFiBalcony
$178/night
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Rustic Adirondack Retreat on Tripp Lake

Rustic Adirondack Retreat on Tripp Lake

3 beds 1 bath
PoolA/CWiFiBalcony
$291/night
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Chestertown Hideaway w/ Lake & Beach Access!

Chestertown Hideaway w/ Lake & Beach Access!

3 beds 2 baths
PoolA/CWiFiBalcony
$442/night
View Details → Book on VRBO
Gorgeous Lakefront Home with a Fire Pit, Two Living Areas, and a Sunroom

Gorgeous Lakefront Home with a Fire Pit, Two Living Areas, and a Sunroom

4 beds 3 baths
PoolA/CWiFiBalcony
$300/night
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Lakefront home steps away from a private, gentle sloping sandy beach & fire pit.

Lakefront home steps away from a private, gentle sloping sandy beach & fire pit.

4 beds 2 baths
PoolA/CWiFiBalcony
$603/night
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Fairview Cabin, Pool, True Adirondack Cabin steps from Loon Lake

Fairview Cabin, Pool, True Adirondack Cabin steps from Loon Lake

4 beds 2 baths
PoolA/CWiFiBalcony
$262/night
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Loon Lake, Chestertown - Spotless, bright chalet - 0.4 mi. from public beach

Loon Lake, Chestertown - Spotless, bright chalet - 0.4 mi. from public beach

4 beds 2 baths
PoolA/CWiFiBalcony
$267/night
View Details → Book on VRBO

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