Downtown Chestertown, New York

Discover shopping, dining, and accommodation in downtown Chestertown.

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Hotels

The Fern Lodge

46 Fiddlehead Bay Rd

Chestertown, New York

Hotel Tips

Avoid booking poolside for kids playing during the day and gatherings at night. Sound bounces off of the water and voices carry so ask for a room away from the pool either on the opposite side of the hotel or in higher floors.

Elevators are notorious for being a nuisance so ask to be roomed on the top floor and as far away as possible. Most hotels book nearby rooms last so hopefully they have availability elsewhere.

Not all online booking systems are fully integrated with hotel reservations systems so there is a chance that smaller hotels are hand entering your stay from a fax machine which leaves room for errors. Book directly with hotel to avoid any problems and ask for a price match if you find a better price online.

Things To Do

Chestertown brings smiles by way of doughnuts and pastries made fresh daily for your enjoyment. Everyone has their favorite of course but having a variety of bakeries is what makes downtown so special. Fritters, scones and pies oh my!

Chestertown hosts several events per year for your listening enjoyment but visit your piano shop to learn how to play and possibly purchase your grand, upright or digital piano. Don't forget the specialty work involved such as tuning and moving which are performed by skilled technicians.

Chestertown has a great collection of barber shops to choose from if you want to take a little off the top, get a clean shave or to trim your moustache or beard. Take a moment to consider buying some styling gel, beard oil or wax and always tip well.

Why Do You Love Downtown?

Amber

The variety of shops!

Carrie AGNEW

why not?

Kim Patrick

There is a lot of unique things to find.

Tracy Hart

Just purchased a home nearby and am looking forward to shopping in the area

Judy Dechent

My daughter and her fiance are relocating from PA to Ashland. They leave next week. I've heard nothing but great things from them and look forward to visiting.

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