Chestertown, MD Vacation Rentals
Our Favorite Vacation Rentals in Chestertown
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Chestertown Vacation Rentals with a Pool
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Chestertown Travel Guide
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.
Things to Do in Chestertown
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!
Best Time to Visit Chestertown
The best time of year to visit Chestertown is during the summer.
Food in Chestertown
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.
The Weather in Chestertown
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.
What Expert Travelers Think
— Packed full of information, from the best time of year to visit (I love NYC in Spring) to top tips from locals, All The Rooms provides the best accommodation, whether you are looking to enjoy your first time visit to New York or want to experience a new location
JazThe Life of a Social Butterfly— My favorite thing about AllTheRooms is that it combines both rentals and hotels available so you can see an entire view of what is available in a certain area. I was able to see listings on AllTheRooms that I never even saw on other travel sites!
Daniella FloresILIKETODABBLE— AllTheRooms.com makes travel easier, enjoyable and inexpensive through its provision of ample information, data and every possible accommodation available to choose from
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Vacation Rentals in Chestertown
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.