Downtown Chestertown, New York

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Hotels

Hotel Tips

Always find a reason to email the front desk manager in hotels that you plan to visit again. Tell them what they did right and express your plans to stay again and ask what opportunities there might be for frequent discounts or upgrades on your next visits. If you become friends with the manager, you just might get the friends and family rate some day.

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.

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 is the place to go when you want to freshen up or replace your nails. Call ahead to schedule an appointment, pick your colors and style and let the transformation begin. Some salons offer hair styling and coloring as well as lashes and eyebrow coloring.

Chestertown makes shopping for wine and other spirits easy by bringing an incredible collection sourced from local, regional well-known producers from around the World. Hit the wine tasting events and stock up on your favorite choice to be shipped home for your convenience.

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.

Why Do You Love Downtown?

Channal Styers
Will be my first visit taking Easter train ride on Saturday to Watertown super excited see what in this great town!

Shari
the scenery, the people, love the activities that go on, even on holidays Ashland is the best to be in, the adventures and animals you can see on a daily bases, and most of all, kid friendly

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.

Holly Harms
We are visiting for the first time!

Caren Murphy
Cute shops, great crab cakes, friendly.