Chestertown travel guide

Chestertown Tourism | Chestertown Guide

You're Going to Love Chestertown

With a population of 5,252, Chestertown is a must-see destination in Maryland, United States. It is among the most popular tourist destinations in the country. Consider staying at least one whole day in Chestertown to see all of its attractions.

Where to Eat in Chestertown

If you’re looking for affordable options, Casa Carmen (312 Cannon St) and The Retriever Bar & The Decoy Bottle Shop (337 1/2 High St) are great picks.

When to visit Chestertown

Chestertown in January
Estimated hotel price
$107
1 night at 3-star hotel
Chestertown in January
Estimated hotel price
$107
1 night at 3-star hotel

Looking for warm weather? Then head to Chestertown in July, when the average temperature is 77 °F, and the highest can go up to 87.8 °F. The coldest month, on the other hand, is January, when it can get as cold as 24.8 °F, with an average temperature of 33.8 °F. You’re likely to see more rain in July, when precipitation is around 4.2″. In contrast, February is usually the driest month of the year in Chestertown, with an average rainfall of 3″.

Data provided by weatherbase
Temperatures
Temperatures
Data provided by weatherbase

How to Get to Chestertown

Plane

Although Chestertown doesn’t have its own airport, you can fly to Greater Wilmington (ILG), which is located 65 km from Chestertown. Philadelphia Airport is the most popular, with regular flights from American Airlines, Air France, Alaska Airlines and other airlines departing from the United States. The shortest domestic flight to Chestertown departs from Fort Lauderdale and takes around 2h 30m.

Train

Amtrak is the only carrier operating train routes to Chestertown. The train journey from Chestertown to Baltimore takes 0h 28m and costs around $5 for a one-way ticket. When coming by train from Philadelphia, expect to pay about $10 for a 1h 55m trip.

Car

Another option to get to Chestertown is to pick up a car rental from New York, which is about 247 km from Chestertown. You’ll find branches of Ace and Kyte, among others, in New York.

Bus

Several bus lines operate bus routes to Chestertown, including Megabus, Bus and CoachRun. From Philadelphia, the bus ride to Chestertown takes 282 km and will cost you around $12. From New York, the ticket costs about $12 for a journey of 443 km.

Plane

Although Chestertown doesn’t have its own airport, you can fly to Greater Wilmington (ILG), which is located 65 km from Chestertown. Philadelphia Airport is the most popular, with regular flights from American Airlines, Air France, Alaska Airlines and other airlines departing from the United States. The shortest domestic flight to Chestertown departs from Fort Lauderdale and takes around 2h 30m.

Train

Amtrak is the only carrier operating train routes to Chestertown. The train journey from Chestertown to Baltimore takes 0h 28m and costs around $5 for a one-way ticket. When coming by train from Philadelphia, expect to pay about $10 for a 1h 55m trip.

Car

Another option to get to Chestertown is to pick up a car rental from New York, which is about 247 km from Chestertown. You’ll find branches of Ace and Kyte, among others, in New York.

Bus

Several bus lines operate bus routes to Chestertown, including Megabus, Bus and CoachRun. From Philadelphia, the bus ride to Chestertown takes 282 km and will cost you around $12. From New York, the ticket costs about $12 for a journey of 443 km.

Airports near Chestertown

Airlines serving Chestertown

Lufthansa
Good (4,662 reviews)
KLM
Good (858 reviews)
SWISS
Good (924 reviews)
British Airways
Good (4,485 reviews)
Delta
Good (4,598 reviews)
Turkish Airlines
Good (2,302 reviews)
Air France
Good (981 reviews)
Iberia
Good (1,557 reviews)
Austrian Airlines
Good (475 reviews)
United Airlines
Good (4,939 reviews)
Emirates
Excellent (2,126 reviews)
Qatar Airways
Good (2,482 reviews)
Air Canada
Good (5,784 reviews)
Brussels Airlines
Good (229 reviews)
Finnair
Good (880 reviews)
TAP AIR PORTUGAL
Good (1,166 reviews)
Scandinavian Airlines
Good (832 reviews)
LOT
Good (682 reviews)
Singapore Airlines
Excellent (916 reviews)
Etihad Airways
Good (832 reviews)
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Where to stay in Chestertown

Average rates range from around $106 per night for a double room in a 3-star hotel to $336 and up for a 5-star experience.

Where to stay in popular areas of Chestertown

Most booked hotels in Chestertown

Brampton Bed and Breakfast Inn
5 stars
Excellent (9.5, 33 reviews)
$336+
Comfort Inn and Suites Chestertown
2 stars
Good (7.6, 274 reviews)
$126+
Driftwood Inn
2 stars
Okay (5.8, 97 reviews)
$69+

Renting a car in Chestertown

Renting a car in Chestertown costs $57 per day, on average.

Expect to pay $3.94 per gallon in Chestertown (average price from the past 30 days). Depending on the size of your rental car, filling up the tank will cost between $47.24 and $62.99.

Renting a car in Chestertown costs $57 per day, on average.

Expect to pay $3.94 per gallon in Chestertown (average price from the past 30 days). Depending on the size of your rental car, filling up the tank will cost between $47.24 and $62.99.