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Find places to stay in Chestertown

Vacation rentals from professional hosts. Book direct, skip the platform markup.

Chestertown Vacation Rentals

Chestertown Vacation Rentals

Find places to stay in Chestertown

Vacation rentals from professional hosts. Book direct, skip the platform markup.

Stop overpaying for
vacation rentals.

Trending stays in Chestertown

6% savings

4 Mi to Beach & Lake: Spacious Home in Chestertown

House in Chestertown, NY

Hosted by Evolve

Mar 11 – Mar 16

6% savings

4 Mi to Beach & Lake: Spacious Home in Chestertown

House in Chestertown, NY

Hosted by Evolve

Mar 11 – Mar 16

'Tree Tops' Retreat ~ 19 Mi to Lake George!

Apartment in Chestertown, NY

Hosted by Evolve

'Tree Tops' Retreat ~ 19 Mi to Lake George!

Apartment in Chestertown, NY

Hosted by Evolve

4% savings

Private Dock & Beach! Lakefront Adirondacks Escape

House in Chestertown, NY

Hosted by Evolve

Mar 11 – Mar 16

4% savings

Private Dock & Beach! Lakefront Adirondacks Escape

House in Chestertown, NY

Hosted by Evolve

Mar 11 – Mar 16

2% savings

Rustic Adirondacks Home w/ Hot Tub & Lake Access!

House in Chestertown, NY

Hosted by Evolve

Mar 15 – Mar 20

2% savings

Rustic Adirondacks Home w/ Hot Tub & Lake Access!

House in Chestertown, NY

Hosted by Evolve

Mar 15 – Mar 20

6% savings

21 Mi to Gore Mtn: Adirondack Oasis w/ Sauna

House in Chestertown, NY

Hosted by Evolve

Mar 11 – Mar 16

6% savings

21 Mi to Gore Mtn: Adirondack Oasis w/ Sauna

House in Chestertown, NY

Hosted by Evolve

Mar 11 – Mar 16

Year-Round Loon Lake Retreat: Ski, Hike, Explore!

House in Chestertown, NY

Hosted by Evolve

Mar 24 – Mar 29

Year-Round Loon Lake Retreat: Ski, Hike, Explore!

House in Chestertown, NY

Hosted by Evolve

Mar 24 – Mar 29

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Nearby Cities

Lake George, NY 12845, USA Oneonta, NY 13820, USA