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Vacation Rentals in Chestertown, New York

about Chestertown

Search vacation deals on homes, villas, cabins, cottages, apartments and condos in destinations all over the world. Click the "rental results" tab to browse Chestertown, New York vacation rentals and inquire about your favorites. If you cant find what youre looking for, consider nearby destinations, or come back for a visit - vacation home rentals in Chestertown are added and updated every week!

Compared to hotels, Chestertown vacation rentals are much more family-friendly and flexible, offering a lot more space, a lot more savings, and a lot more amenities - like private pools, gourmet kitchens, and pet-friendly accommodations! Tip: Save money by taking advantage of cheap weekly rates.

Chestertown, New York Vacation Rentals and Tourism

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Check out more areas which feature homes, villas, cabins, cottages, or condos.

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Weekly rate:

Min $0, Max $4000

$0
$2,000
$4,000+

Bedrooms: Min 0, Max 5

0
5+







Property Type:


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has swimming pool
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* Nightly rates and average rates per bedroom are based on actual rates in this area. Learn More .

Tripp Lake Front House
Chestertown House Rental Picture
  • bedrooms 5
  • community
  • rental type House
  • sleeps 12
  • baths 3
  • rates (USD) $250 - $300 /nt
    $1,450 - $2,950 /wk
 
 
 
 
 

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Mountain Retreat on Private Lake 'Alderbrook Lodge'
Chestertown Lodge Rental Picture
  • bedrooms 8
  • rental type Lodge
  • owner badgeowner badge
  • sleeps 16
  • baths
  • rates (USD) $700 - $800 /nt
    $11,800 /wk
 
 
 
 
 

8 reviews write a review

Beautiful Loon Lake Family Resort In The Adirondack Mountains
Chestertown Lodge Rental Picture
  • bedrooms 6
  • rental type Lodge
  • sleeps 11
  • baths 2
  • rates (USD) $695 - $2,150 /wk
 
 
 
 
 

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Large, Historic Adirondack Vacation House with in ground pool and wifi
Chestertown House Rental Picture
  • bedrooms 6
  • rental type House
  • owner badgeowner badge
  • sleeps 20
  • baths 3
  • rates (USD) $750 /nt
    $4,550 /wk
 
 
 
 
 

9 reviews write a review

A Family Friendly, 4 Season Favorite Located On Loon Lake, Near Gore Mountain
Chestertown House Rental Picture
  • bedrooms 6
  • rental type House
  • sleeps 16
  • baths 3
  • rates (USD) $350 /nt
    $2,000 /wk
    $7,000 /mth
 
 
 
 
 

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