Downtown Chestertown, New York

Hotels

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.

Upon check-in, slip the desk agent a tip and ask for the best room they can find at your current booked rate. Often times a quick $10 or $20 bill can go a long way towards the mood of the person who directly decides where you lay your head for the night.

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.

Things To Do

Chestertown brings the farming community under one marketplace to offer an assortment of locally grown fruit and vegetables. Traditionally, markets are restricted to anything grown so you can expect to see natural whole foods that are sure to please those working on their plant-based diets!

Chestertown offers on-the-go dining when you visit your favorite food truck. Pick up some corn tortilla tacos with freshly made pico with a fresh squeeze of lemon to give your day a boost. Food trucks can offer a wide variety of niche ethnic blends.

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.

Why Do You Love Downtown?

Liisa Shunn
We love going downtown, because we like to support our local economy. The shops and restaurants we visit -- we have gotten to know the owners, so when our money is spent downtown, we know who benefits. Also? We live only a mile from downtown, so we walk or ride our bikes. No worries about a designated driver or looking for parking. We chose to live in Medford, so of course we want our money to stay in Medford, not going off to some corporate office of a chain store.

Ariel
i have been here since 2005 and fell in love with downtown, the shops are amazing, good prices, nice people, great gifts ect... the scenery is wonderful as well

Debbie Kimpel
We are coming in August to visit . My husband is related to Esther, the town was named after. We would like to visit some Historial areas there and also visit the downtown area as well.

Michelle Reesey
Haven't been there yet. Trip is planned in April.

Deborah
Jacksonville is utterly charming! I love browsing Terra Firma and Pickety Place, eating delicious Umi Sushi, and sitting under the amazing wisteria in the Bella Union garden. I always go to the library in that sweet little building, where Lauren the librarian knows me by name (and recommends good books). The Good Bean people are awfully nice, and even the clerks at Umpqua Bank are especially kind and friendly. Best little downtown ever!

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