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Search Hotels in and near Chestertown

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Top 3 Hotels in and near Chestertown, Maryland, United States

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3 of 5 Stars

150 Scheeler Road, Chestertown, MD 21620, USA

Welcome to the Holiday Inn Express and Suites in Chestertown, MD. We have what you need to make your stay a great one. The location of our hotel is convenient for shopping and dining, as we are across the street from the Kent Plaza shopping center. The hotel has a business center, fitness center and a indoor heated pool for your enjoyment....

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Approximately 1.31 Miles away from Chestertown center
2 of 5 Stars

609 Washington Avenue, Chestertown, MD 21620, USA

Escape from the busy hustles and stress of life and let us pamper you at Driftwood Inn Combining traditional hospitality and luxurious accommodation we offer guests outstanding service and a comfortable stay all at affordable prices We are committed to providing our guests with the best we have to offer surpassing guest expectations Unwind...

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Approximately 0.96 Miles away from Chestertown center
2 of 5 Stars

20748 Rock Hall Avenue, Rock Hall, 21661, USA

The Haven Point Inn and Gallery is a brand new contemporary inn and gallery located on the Eastern Shore in beautiful Rock Hall Maryland. The beautifully appointed rooms were designed with your comfort in mind. With ultra plush mattresses hand ironed silky Egyptian cotton sheets extra pillows roomy bath state of the art eco friendly heat and...

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Approximately 11.1 Miles away from Chestertown center

Chestertown Frequently Asked Questions

Question: How's the seasonal weather in Chestertown?

Answer: Chestertown Seasonal temperature break down - The average median temperature March through May is approximately 55°F with highs averaging at 63°F and lows averaging at 50°F. June through August has an approximate average median temperature of 76°F with highs averaging at 83°F, lows typically average at 71°F. Average median temperatures September through November average out at 59°F, high temperatures average out at 66°F and lows average at 53°F. The average median temperature December through February is approximately 37°F with highs averaging at 43°F, lows average out at 32°F. The average Chestertown annual median temperature averages out at approximately 57°F. The coldest month in Chestertown is January with a median temperature of 35°F, the average high for the month of January is 41°F with an average low of 30°F. The hottest month in Chestertown is July with an approximate median temperature of 80°F, the average high for the month of July is 87°F with an average low of 74°F.

Question: What type of clothing should I pack for my trip to Chestertown?

Answer: If you plan on traveling to Chestertown from March through May you will want to pack a couple of lightweight long sleeve shirts, lightweight jeans or pants. You should also think about packing a couple of t-shirts and possibly a pair of shorts for the hotter days, for the cooler days or nights you may want to think about packing a lightweight jacket or a lightweight sweater. Those of you who will be traveling to Chestertown from June through August should think about packing some short sleeve shirts and shorts. You may also want to pack a tank top as it can sometimes get pretty hot during the day. You should also consider packing a lightweight long sleeve shirt and jeans as there's a possibility you can run into a cooler night. Folks that will be traveling to Chestertown September through November may want to consider packing a couple of lightweight long sleeve shirts and jeans, you will also want to consider packing a lightweight jacket for cooler days or nights. Those of you that will be traveling to Chestertown from December through February will want to pack a number of heavy sweaters, long sleeve shirts, jeans, gloves, a heavy jacket, ear muffs will also be a good idea.

Question: Where can I get a bite to eat during my Chestertown stay?

Answer: Chestertown has a decent amount of places to eat at please see the following list of our top choices of places to eat during your stay in Chestertown.

Question: What are some notable places I should visit during my stay in Chestertown?

Answer: When it comes to sightseeing in Chestertown there's a number of places we recommend that you visit such as Kent County Health Center, Chestertown Historic District, Buck Bacchus Store Museum... See the full list

Question: Where can I party or get a round of drinks with the buddies during our Chestertown visit?

Answer: Chestertown has a number of bars where you could party or get a round in with buddies. We have gone ahead and compiled a list of our top choices please feel free to have a look.

Places To Eat At - During Your Chestertown Visit

Restaurants
Cafe Sado - Sushi Restaurant - Chestertown, Maryland
Ritas Italian Ice - Restaurant - Chestertown, Maryland
Play It Again Sam - Restaurant - Chestertown, Maryland
The FREEZE - Restaurant - Chestertown, Maryland

Sightseeing - Places to Visit During Your Stay in Chestertown

Kent County Health Center - Historical Buildings - Chestertown
Chestertown Historic District - Historical Buildings - Chestertown
Buck Bacchus Store Museum - Museum or Art Gallery - Chestertown
Roundtop Park - Park - Chestertown
Kings Town Park - Park - Chestertown
Wilmer Park - Park - Chestertown
Remington Farms National Wildlife Preserve - Park - Chestertown

Nightlife - Where to Party During Your Chestertown Visit

Bars
Jellyfish Joels Tiki Bar - Bar - Chestertown, Maryland
Howards Tavern - Bar - Chestertown, Maryland
Blue Bird Tavern - Bar - Chestertown, Maryland
OConnors Pub Restaurant - Bar - Chestertown, Maryland
The Sandbar At Ralphs Marina - Bar - Chestertown, Maryland

Top 3 hotels in Chestertown - Map View

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Holiday Inn Exp Stes Chestertw
Holiday Inn Exp Stes Chestertw
$89
Driftwood Inn
Driftwood Inn
$61
Haven Point Inn and Gallery
Haven Point Inn and Gallery
$145
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