Chestertown is located in Maryland, east of Baltimore. It is an excellent vacation spot for family fun, a couples’ getaway or even a long weekend away with friends. Chestertown is mainly known for being a quaint mid-Atlantic town.
To learn more about the city, you are definitely going to want to check out the self-guided downtown tour, it’s a must see and a great opportunity for everyone in your group. The Chestertown River cruise is also a great option if you want to see more of the city.
Another top activity is to roam the aisles of the Chestertown Farmer's Market and Artisan's Market and buy some vacation gifts for loved ones, and of course, some treats for yourself!
The best time of year to visit Chestertown is during the summer.
There are some mouthwatering spots for foodies to sample when visiting Chestertown. The two that stand out are Luisa's Cucina Italiana, which is known for having some of the best Italian food in the area, or if you like seafood, check out Fish Whistle.
This climate histogram shows you the weather patterns in Chestertown. The warmest months in Chestertown are June and May, when temperatures reach 97 ˚F. The coolest month is December, when temperatures drop to 2 ˚F. The wettest month in Chestertown is August with 8.2 inches of rain, while the driest month is May with 2.36 inches of rain.
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Choose the perfect rental for your vacation at AllTheRooms.com. We aggregate Airbnb, Bed and Breakfast, Priceline and more. We have 166 vacation rentals, hotels and other accommodation types in Chestertown ranging from inexpensive options to extravagant places to stay. For those traveling on a budget, the most economical place to stay in Chestertown is available at $55 per night. The average price of a vacation rental is around $323 per night.
If you need an internet connection during your time in Chestertown, then you can choose from over 80 accommodations that provide WiFi internet. 21 of our accommodations come with breakfast in the price. You can maintain your workout regime by staying at one of 4 accommodations that provide gym facilities. Driving to Chestertown? Then choose one of the 75 places to stay that comes with a parking spot included. 9 vacation rentals have a a pool or jacuzzi
If you're traveling with a furry friend, then be sure to choose one of the 23 pet-friendly accommodations available.
108 accommodations in Chestertown have been reviewed; 72% are rated excellent or good. 32 accommodations allow instant booking.