Downtown Chestertown, Maryland

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Hotels

Hotel Tips

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.

Elevators are notorious for being a nuisance so ask to be roomed on the top floor and as far away as possible. Most hotels book nearby rooms last so hopefully they have availability elsewhere.

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.

Things To Do

Chestertown shopping is better than online shopping so that you can touch, feel, smell and taste as an experience with an item before deciding to purchase it for yourself or as a gift. Local merchants have hand selected their inventory to provide a unique selection for your downtown.

Chestertown keeps your pets fed, groomed, clothed and entertained with a wide assortment of ts.s available online and in-store. Does your dog need a bit of training? Check with us for great referrals to dog walkers, trainers and veterinarians who can work with your pets.

Chestertown helps you expand your skills and learn some new ways to expand your artisan flare? Sign up for classes at your kitchen supply store, yarn shop, art and craft shop and photo gallery. You'll be having great fun with your new friends as you you take on that next project.

Why Do You Love Downtown?

Darby
Visiting in July for the 1st time!

Sharon Skipton
Will be there in a week. Looks like a great town!

Tracy Hart
Just purchased a home nearby and am looking forward to shopping in the area

Rita
Maureen is there

Kim Knox
All the quaint shops, I like to support small business.