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Chestertown

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Map of Chestertown Hotels

Hotels (1)

B&Bs / Inns (7)

Specialty Lodging (2)

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46 Fiddlehead Bay Road, Chestertown, NY 12817
The Fern Lodge Slideshow
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$417 - $577 Avg. price/night*
Ollie #1 of 7 B&Bs / Inns in Chestertown
  •  Perfect in every way 
  • We stayed two nights in the Birch Room and found everything as... more
  • September 10, 2014
Professional photos | Traveler photos (92)
Special Deal Fall Whitewater Rafting!
963 Friends Lake Rd., Chestertown, NY 12817
Friends Lake Inn Slideshow
$349 - $499 Avg. price/night*
Ollie #2 of 7 B&Bs / Inns in Chestertown
  •  Consistency is a Virtue 
  • I've been going to the Friends Lake Inn for approximately 15 years. I've... more
  • September 15, 2014
Traveler photos (52)
5537 State Rt 8, Chestertown, NY 12817-2403
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$50 - $150 Avg. price/night*
Ollie #1 of 1 hotels in Chestertown
  •  Andy and Anne 
  • We stayed here on a whim passing by, and I was extremely pleased with... more
  • August 26, 2014
Traveler photos (28)
6347 Main Street, PO Box 163, Chestertown, NY 12817
$75 - $125 Avg. price/night*
Ollie #3 of 7 B&Bs / Inns in Chestertown
  •  Fortuitous Find 
  • To start Chester Inn wasn't the first inn I booked for my trip to Lake... more
  • July 10, 2013
Traveler photos (3)
5381 State Rte 8, Chestertown, NY 12817
Show Prices
$70 - $105 Avg. price/night*
Ollie #4 of 7 B&Bs / Inns in Chestertown
Professional photos | Traveler photos (1)
10 Landon Hill Road, Chestertown Ny, Chestertown, NY 12817
$75 - $120 Avg. price/night*
Ollie #5 of 7 B&Bs / Inns in Chestertown
  •  Quaint & Hospitable 
  • We stayed one night at this lovely B&B for a wedding we were attending... more
  • October 24, 2013
Traveler photos (6)
6359 State Route 9, Chestertown, NY 12817
No photo provided
$70 Avg. price/night*
Ollie #6 of 7 B&Bs / Inns in Chestertown
  •  Bargin 
  • We drove 2 1/2 hours from Highland NY to Chestertown NY. We were looking... more
  • March 25, 2013
Friends Lake, Chestertown, NY 12817