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

Bring an actual credit card to avoid deposits and pre-authorizations consuming money in your checking account which will reduce your available balance. Hotels that accept paper cash often ask for a hefty deposit to cover potential damages in your room leaving you scrambling to find an ATM.

Policies vary on the availability of pet friendly rooms to it is wise to be open, honest and upfront during the booking process. You may find yourself kicked out or even paying a large deposit if you are not in a pet-friendly hotel and bring one anyway. New ADA laws are fuzzy though as service animals are not required to be documented and proprietors are legally not allowed to ask if the animal is a pet vs. a service animal.

Ask to be shown a room before you check-in which signals the front desk agent to show the best room available to sell it right away. This can put you in the best room available at that time and gives you the ability to check for cleanliness, smells and sounds before transacting with the hotel.

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 shopping is better than online shopping so that you can touch, feel, smell and taste as an experience with an item before deciding to purchase it for yourself or as a gift. Local merchants have hand selected their inventory to provide a unique selection for your downtown.

Chestertown has that special dining venue and you are sure to find something to please with numerous meals served to satisfy each palette. A wide variety of restaurants and delis are available to choose from with a nice selection of entrees and especially desserts.

Why Do You Love Downtown?

Millie

So unique!

Michelle Kleyne

Great vibe

Mary Ann Schlumpberger

It is just a fun place to go! Love Blind Georges' popcorn

Shawna Moore

I like the old school charm and love supporting the local merchants!

Diane morgon

We are coming to visit and looks very interesting.

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