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Chestertown Vacation Rentals

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0+ rooms, 2+ guests
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$1,000+
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44 rentals in Chestertown.
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Atateka Point Lodge and Treehouse Guest Cottage
4 bedrooms
3 bathrooms
Sleeps 10
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31 other travelers have booked this property
2020
Black Bear Cabin
2 bedrooms
2 bathrooms
Sleeps 4
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70 other travelers have booked this property
Well maintained Adirondack Lakeside Condo. Kid & Pet Friendly
2 bedrooms
1 bathroom
Sleeps 6
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Green Mansions Vacation Condo
2 bedrooms
2 bathrooms
Sleeps 6
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34 other travelers have booked this property
Loon Lake Retreat with Private Dock
3 bedrooms
2 bathrooms
Sleeps 8
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25 other travelers have booked this property
Adorable log home w/ a full kitchen - river frontage close by!
2 bedrooms
2 bathrooms
Sleeps 7
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The Roost, a lakefront 4 season home in the Adirondack Mountains
4 bedrooms
3 bathrooms
Sleeps 9
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Updated Adirondack Townhouse w/Mountain Views- Close to Lake George & Gore
2 bedrooms
2 bathrooms
Sleeps 6
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The Treehouse at Atateka Point Lodge
2 bedrooms
2 bathrooms
Sleeps 4
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19 other travelers have booked this property
Year round lake front LOG CABIN on over 2 acres on Loon Lake updated in 2018
5 bedrooms
3 bathrooms
Sleeps 14
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Relax at Our River Retreat
4 bedrooms
2 bathrooms
Sleeps 10
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A beautiful family camp/Lake House on Loon Lake in the Adirondacks in NYS
5 bedrooms
3 bathrooms
Sleeps 13
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Adirondack Getaway at Tripp Lake
2 bedrooms
2 bathrooms
Sleeps 4
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Lakefront cabin with beautiful loft, game room, views, private dock
5 bedrooms
3 bathrooms
Sleeps 12
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Historic Greek Revival style home w/ screened in porch -near attractions!
6 bedrooms
5 bathrooms
Sleeps 11
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Single-level, spacious house w/ firepit & spacious yard - lake access nearby
4 bedrooms
2 bathrooms
Sleeps 8
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Friends Lake- Quaint and New
2 bedrooms
2 bathrooms
Sleeps 7
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5 other travelers have booked this property
ADK Home near Gore Mountian
4 bedrooms
2 bathrooms
Sleeps 10
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Comfortable year round Lake house on Loon Lake perfect for a getaway
4 bedrooms
3 bathrooms
Sleeps 8
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Enormous lakefront house with high-end touches, private dock
6 bedrooms
4 bathrooms
Sleeps 12
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Beautiful family friendly lakefront house with dock, beach, multiple decks
5 bedrooms
3 bathrooms
Sleeps 6
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Deer Run Cabin at Twin Pine Lodge
3 bedrooms
1 bathroom
Sleeps 6
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#2 Hillside * Birchwood Cottages at Loon Lake. Family Friendly Waterfront
3 bedrooms
2 bathrooms
Sleeps 4
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Single-level, spacious house w/ firepit & spacious yard - lake access nearby
4 bedrooms
2 bathrooms
Sleeps 6
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1 other traveler has booked this property
Enormous lakefront house with high-end touches, private dock
6 bedrooms
4 bathrooms
Sleeps 12
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One bedroom cottage has great amenities & several weeks available for 2020.
1 bedroom
1 bathroom
Sleeps 2
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Dog-friendly, lakefront camp cabin w/ a dock & multiple decks
3 bedrooms
2 bathrooms
Sleeps 6
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Dog-friendly, lakefront house with 2 living areas, beach nearby
4 bedrooms
4 bathrooms
Sleeps 8
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1 other traveler has booked this property
Gorgeous condo w/ golf court views, shared pool, and shuttle to the beach!
1 bedroom
1 bathroom
Sleeps 3
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Family-friendly coastal condo with shared pool, hot tub and easy beach access!
2 bedrooms
2 bathrooms
Sleeps 8
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Gorgeous and spacious beachfront condo with shared pool and beach access
2 bedrooms
2 bathrooms
Sleeps 4
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Adorable log home w/ a full kitchen - river frontage close by!
2 bedrooms
2 bathrooms
Sleeps 5
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Fairview at Twin Pine Lodge
4 bedrooms
2 bathrooms
Sleeps 8
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One-of-a-kind coastal condo w/Gulf views, shared pool, and easy beach access
2 bedrooms
2 bathrooms
Sleeps 8
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Historic Greek Revival style home w/ screened in porch -near attractions!
6 bedrooms
5 bathrooms
Sleeps 11
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Cozy cottage with deeded lake rights - 100 steps to the beach
4 bedrooms
2 bathrooms
Sleeps 8
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NEW LISTING! Lakefront cabin with sandy beach, dock, multiple fireplaces
4 bedrooms
2 bathrooms
Sleeps 11
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Beautiful family friendly lakefront house with dock, beach, multiple decks
5 bedrooms
3 bathrooms
Sleeps 6
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Charming oceanfront cottage w/enclosed porches, steps to the water! Dogs OK!
5 bedrooms
2 bathrooms
Sleeps 8
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Gorgeous condo w/golf course and mountain views and shared pool & spa!
2 bedrooms
2 bathrooms
Sleeps 4
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Family-friendly coastal condo with shared pool and easy beach access
2 bedrooms
2 bathrooms
Sleeps 8
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Secluded home in forestlake rd with 2 acres located in warrensburg
2 bedrooms
2 bathrooms
Sleeps 5
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Lakefront house with private beach and dock, multiple decks
4 bedrooms
2 bathrooms
Sleeps 9
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Waterfront & family-friendly home w/ deck,great views, full kitchen & WiFi!
1 bedroom
1 bathroom
Sleeps 6
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