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.
Browse places to stay from all the best providers including Airbnb, Bed and Breakfast, Priceline and others at AllTheRooms.com. We have 154 vacation rentals, hotels and other places to stay in Chestertown ranging from low-cost options to luxury places to stay. For those wanting to keep costs down, the cheapest place to stay in Chestertown is just $55 per night. An average accommodation in Chestertown costs on average $294 per night.
Those looking to get some work done during their trip to Chestertown can pick from 73 places to stay that include WiFi. 20 of our accommodations include a breakfast in the price. Fitness fanatics can get a workout in during their stay by choosing from 3 accommodations that have gyms. If you're planning on arriving in Chestertown by car, be sure to choose from 68 accommodations that provide parking. 8 accommodations have a a pool or jacuzzi
Those traveling with a cat, dog or some other animal can stay in one of 18 accommodations that are designated as pet-friendly.
99 of the accommodations in Chestertown have been reviewed and rated. 68% are rated great. 32 places to stay in are instantly bookable.