Chestertown Holiday Rentals
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104 rentals in Chestertown.
Adirondack Base Camp by Loon Lake and Gore Mt.!
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Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
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Cozy retreat with fireplace, kayaks, and shared beach/pond access
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Welcome home!
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Year round Log Cabin on Loon Lake. Minutes from skiing at Gore Mountain
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Eagles Nest at Loon Lake near Gore Mountain
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#4 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!
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Winter in the Adirondacks
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Secluded gem with forest view, beach access & W/D
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Private child-friendly home with game room, high-speed WiFi, and wraparound deck
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TRIPP LAKE RETREAT sleeps 7 and is a great place to make Adirondack memories!
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Lakefront Home - 20 Min from Gore Mountain w/Hot Tub
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Adirondack “River Rapture"- Lake George/Mount Gore
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Lakefront spacious contemporary. Large families welcome. Ski GORE nearby!
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Lily Pad South at Loon Lake near Gore Mountain
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Peaceful Lakeside Retreat with Private Beach
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Rustic Adirondack Retreat on Tripp Lake
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The Roost, a lakefront 4 season home in the Adirondack Mountains
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Tripp Pond Retreat, Unit E | Condo in Warrensburg
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Stock Farm, an Adirondack Gem
Condo/Apartment
0 bedrooms
0 bathrooms
Sleeps 8
Match: Sleeps
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Chipmunk Cabin, Beautiful hand carved King Bed, Full Kitchen, plus AC! sleep 2
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Deer Crossing, A Beautiful Loon Lake Family Cabin in the Adirondack Mountains
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Classic riverfront cottage w/ beautiful water views, WiFi, & screened porches
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Hide-A-Way Cabin, Pool & AC, Authetic Adirondack Cabin Steps from Loon Lake
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Dog-friendly cabin with lakefront location, 20' dock, smart TV
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Lily Pad North at Loon Lake near Gore Mountain
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Fireside Cabin, Pool & AC, Wonderful Cozy Adirondack Cabin steps from Loon Lake.
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Raccoon Retreat, 2 Bedroom 1 Bath Cabin, Sleeps Up to 6 People
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lakefront cabin with beautiful views, lake and beach access
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Two Bedroom Riverfront Log Cabin
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A beautiful lake view cabin on Friends Lake
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Beautiful lakeview cottage on Friends Lake
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Lakefront Home with WiFi, Dock, Lake Views From the Deck, and Screened-In Porch
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Rangers Retreat Adirondack Mountains getaway
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lower Chalet, Gore Mountain Skiing, Pool/AC/Woodstove, Cozy Cabin, Loon Lake.
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Adorable 2 bedroom 2 Bathroom
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Log Haven Cabin, Gore Mountain Skiing, Pool/AC/Fireplace,Steps to Loon Lake
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Adirondack JEM - 20 Minutes to Lake George or Gore Mountain for Four Season Fun!
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Private Adirondack lakefront Cottage on Loon Lake
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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2-Story Home w/Pond Views, Gas Grill, Fire Pit, Washer/Dryer, and Partial A/C
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Base Camp.
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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#7 Adirondack*Birchwood Cottages on Loon Lake. Family Friendly Waterfront
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Bass Bunk, A Beautiful Loon Lake Family Cabin in the Adirondack Mountains
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Sleepy Hollow, Gore Mountain Skiing, Pool/AC/Fireplace,Cabin Steps to Loon
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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#6 Lakeview *Birchwood Cottages at Loon Lake. Family Friendly Waterfront
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Loon's Lair, A Beautiful immaculate Adirondack 2 Bedroom 3 Bathroom Suite
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Peaceful retreat in the heart of the Adirondacks.
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Adirondack home, near Gore Mt ski resort, North Creek, and Loon lake.
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Deer Run, Gore Mountain skiing, pool, steps from Loon Lake
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Chalet Cabin, Gore Mountain SKiing, Pool/AC/Woodstove, Spacious Cabin, Loon
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Showing results 1-50 of 104
Frequently Asked Questions about Chestertown
- Yes, here are some popular holiday rentals in Chestertown that have a pool:
- Adirondack Base Camp by Loon Lake and Gore Mt.!
- Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
- Cozy retreat with fireplace, kayaks, and shared beach/pond access
- Yes, here are some popular holiday rentals in Chestertown that have internet access:
- Adirondack Base Camp by Loon Lake and Gore Mt.!
- Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
- Cozy retreat with fireplace, kayaks, and shared beach/pond access
- The best pet friendly rentals in Chestertown are:
- Adirondack Base Camp by Loon Lake and Gore Mt.!
- Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
- #4 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!
- Some of the most popular kid friendly rentals in Chestertown are:
- Adirondack Base Camp by Loon Lake and Gore Mt.!
- Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
- Cozy retreat with fireplace, kayaks, and shared beach/pond access
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