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

Call ahead to make sure your reservation is still active and rebook if there are any price drops or changes in number of people staying with you. Another cost saving tips is to bundle the stay with airport parking and shuttle to avoid hefty fees.

Always tip staff when you feel the service was great and don't forget the housekeeping staff which you may never see. You should tip every day if you are staying multiple days as the staff may rotate out and miss the bounty at the end.

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 has several options for shopping for specialty food items that are not found in regular grocery stores. Shops tailored for "foodies" offer tastings of the products as well as scheduled culinary classes to perfect your skills. Shop for infused oils, salts and spices from around the World!

Chestertown is the place to plan your wedding. You'll be spending a lot of time downtown as there are so many wonderful shops to find invitations, photographers, bakers, caterers and jewelers. Planning your wedding will be a breeze with so much support from local merchants to make a perfect and memorable day.

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?

kristin Cutler

It's so cute and quaint.

Erin Lawless

The shops and bakery make it an appealing destination for people who want to keep small businesses going by enjoying those shops as well

heather ashbaker

this will be my first visit

Laurie MvNamara

Love all the shopping and beautiful place to be!

Tammy Benson

Shopping eating and site seing

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