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Chestertown

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Map of Chestertown Hotels

Hotels (1)

B&Bs / Inns (8)

Specialty Lodging (4)

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Hotels Travelers Trust

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46 Fiddlehead Bay Rd, Chestertown, NY 12817-1949
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$434 - $578 Avg. price/night*
Ollie #1 of 8 B&Bs / Inns in Chestertown
  •  Romantic gwtaway 
  • Great place. Wonderful wine cellar. Fire pits everywhere with... more
  • February 13, 2017
Professional photos | Traveler photos (176)
Offers & Announcements Ski free w/midweek stay!
963 Friends Lake Rd., Chestertown, NY 12817
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$189 - $335 Avg. price/night*
Ollie #2 of 8 B&Bs / Inns in Chestertown
Professional photos | Traveler photos (61)
Special Offer Date Night Deal
5537 State Route 8, Chestertown, NY 12817-2403
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$135 - $149 Avg. price/night*
Ollie #1 of 1 hotels in Chestertown
Professional photos | Traveler photos (51)
6347 Main Street, PO Box 163, Chestertown, NY 12817
$75 - $125 Avg. price/night*
Ollie #3 of 8 B&Bs / Inns in Chestertown
  •  The Perfect B and B 
  • This was the best B and B we've ever stayed in. It was beautiful... more
  • August 9, 2015
Traveler photos (3)
6359 State Route 9, Chestertown, NY 12817-2535
Ollie #4 of 8 B&Bs / Inns in Chestertown
  •  Panther Mountain Pub 
  • Great bar. Very comfortable. Would definitely recommend it to everyone... more
  • December 30, 2016
5064 State Route 8, Chestertown, NY 12817-3609
Ollie #5 of 8 B&Bs / Inns in Chestertown
Traveler photos (1)
5381 State Rte 8, Chestertown, NY 12817
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$126 - $127 Avg. price/night*
Ollie #6 of 8 B&Bs / Inns in Chestertown
  •  Loved it!! 
  • The owner, Bob, greeted us warmly. Rooms were very spacious, very clean... more
  • October 11, 2016
Professional photos | Traveler photos (22)
10 Landon Hill Road, Chestertown Ny, Chestertown, NY 12817
$75 - $120 Avg. price/night*
Ollie #7 of 8 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)
Friends Lake, Chestertown, NY 12817