Downtown Chestertown, Maryland

Discover shopping, dining, and accommodation in downtown Chestertown.

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Hotels

Comfort Suites Chestertown

160 Scheeler Rd

Chestertown, Maryland

Holiday Inn Express Hotel & Suites Chestertown

150 Scheeler Road

Chestertown, Maryland

Hotel Tips

Most hotel offer a complimentary breakfast bar or even a full cafe meal with your choice of a full menu. Keep in mind that some offer nothing at all so it is a good idea to pack a few packets of instant oatmeal for a quick and easy meal before you head out for the day.

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.

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.

Things To Do

Chestertown visitors are always welcome and you will receive exceptional service from local merchant-owners as opposed to staff at the big box retailers. We take the extra time to make sure that you how to make best use of your purchase and that you get exactly what you need.

Chestertown is a great place to rent a bike and take it for a ride around downtown. There are many bike shops that sell bike and accessories as well as provide service and tuning on your ride. Don't forget your helmet and other protective gear such as reflective gear, headlight and horn.

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.

Why Do You Love Downtown?

Ann Kimball

We are going to be visiting Rockport for our upcoming wedding anniversary!

Melanie Kraus

I have not been there in a long time. Last time I was there was with my parents. I thought it was neat little town back then. Could you send me some information on reelsville Indiana.

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

Joyce gugger

Very relaxing ! Nice folks on the west coast

Richard Held

Unique shops.

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