Downtown Chestertown, Maryland

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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

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.

Always announce during booking if the trip is for a special event, anniversary or reunion. Group rates can be pre-negotiated and you may qualify for a lower cost and better upgrades for your stay. If you are the one setting up the event, always work directly with the front desk manager to make sure the best service is offered to your party.

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.

Things To Do

Chestertown micro breweries have popped up in downtown corridors to quench the thirst of local or traveller whos is looking for a one-of-a-kind experience for suds brewed on site. If you are looking for a light beer or something randy and dark, you are sure to find a wide assortment of options to choose from.

Chestertown brings musicians together and finding your local musical instrument shop can be a great way to get to try new and used guitars. Be sure to start your search downtown if you are looking to upgrade, trade-in or add to your collection.

Chestertown can warm you up on a cloudy day or simply offer your daily perk by visiting your local coffee shop. Quality, purity and punch are targeted with coffee beans curated globally and locally roasted while being served fresh as it is made right in front of you. Order up!

Why Do You Love Downtown?

Michelle Kleyne

Great vibe

Michelle Goodrich

Nice Shops

Judy Caverly

Interesting shops, good restaurants, friendly people.

HILDA SMITH

It has some unique stores.

carl barbieri

were there on business at least 7 times a year ,We just love downtown medford

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