Chestertown Vacation Rentals
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92 rentals in Chestertown.
Adirondack Base Camp by Loon Lake and Gore Mt.!
Rental Home
2 bedrooms
1 bathroom
Sleeps 8
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Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 6
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Cozy retreat with fireplace, kayaks, and shared beach/pond access
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
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Welcome home!
Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
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Lakefront cabin with beautiful loft, game room, views, private dock
Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
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Year round Log Cabin on 2 acres on Loon Lake. Minutes from Gore
Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
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Adirondack style condo on Tripp lake and near Gore Mt. Ski resort
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Eagles Nest * Loon Lake near Gore Mountain
Rental Home
7 bedrooms
4 bathrooms
Sleeps 20
Match: Sleeps
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#4 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!
Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Condo with private community beach/pond access - on-site tennis & golf nearby
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Adirondack House Rental on Loon Lake
Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Secluded dog-friendly gem with forest view, beach access, WiFi & private W/D
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Private Child-Friendly Home with Game Room, High-Speed WiFi, and Wraparound Deck
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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TRIPP LAKE RETREAT, a great place to make Adirondack memories!
Rental Home
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Lakefront Home - 20 Minutes from Gore Mountain
Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Adirondack “River Rapture"- Lake George/Mount Gore
Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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1 Family Friendly Waterfront on Loon Lake. Boating, fishing, swimming!
Rental Home
4 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Lily Pad South at Loon Lake near Gore Mountain
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
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Peaceful Lakeside Retreat with Private Beach
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Rustic Adirondack Retreat on Tripp Lake
Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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The Roost, a lakefront 4 season home in the Adirondack Mountains
Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Tripp Pond Retreat, Unit E | Condo in Warrensburg
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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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
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Deer Crossing, A Beautiful Loon Lake Family Cabin in the Adirondack Mountains
Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Classic Riverfront Cottage W/ Beautiful Water Views, Free WiFi & Screened Porch!
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Hide-A-Way Cabin, Pool & AC, Authetic Adirondack Cabin Steps from Loon Lake
Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Dog-friendly cabin with lakefront location, 20' dock, smart TV
Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lily Pad North at Loon Lake near Gore Mountain
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Fireside Cabin, Pool & AC, Wonderful Cozy Adirondack Cabin steps from Loon Lake.
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Raccoon Retreat, 2 Bedroom 1 Bath Cabin, Sleeps Up to 6 People
Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lakefront cabin with beautiful views, lake and beach access
Rental Home
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Two Bedroom Riverfront Log Cabin
Rental Home
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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A beautiful lake view cabin on Friends Lake
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful lakeview cottage on Friends Lake
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Lakefront Home with WiFi, Dock, Lake Views From the Deck, and Screened-In Porch
Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Rangers Retreat Adirondack Mountains getaway
Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lower Chalet, Pool & AC, Adorable, Cozy Adirondack Cabin steps from Loon Lake.
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Adorable 2 bedroom 2 Bathroom
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Log Haven, Pool & AC, Cozy Adirondack Mountains Cabin Steps from Loon Lake
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Adirondack JEM - 20 Minutes to Gore Mountain or Lake George for Four Season Fun!
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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2-Story Home w/Pond Views, Gas Grill, Fire Pit, Washer/Dryer, and Partial A/C
Rental Home
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Base Camp.
Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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#7 Adirondack*Birchwood Cottages at Loon Lake. Family Friendly Waterfront
Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Bass Bunk, A Beautiful Loon Lake Family Cabin in the Adirondack Mountains
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sleepy Hollow, Pool&AC,Wonderful Adirondack Mountains Cabin Steps from Loon Lake
Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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#6 Lakeview *Birchwood Cottages at Loon Lake. Family Friendly Waterfront
Rental Home
4 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Loon's Lair, A Beautiful immaculate Adirondack 2 Bedroom 3 Bathroom Suite
Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Peaceful retreat in the heart of the Adirondacks.
Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Adirondack home, near Gore Mt ski resort, North Creek, and Loon lake.
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Frequently Asked Questions about Chestertown
- Yes, here are some popular vacation 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 vacation 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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