Chestertown, MD Vacation Rentals
Our Favorite Vacation Rentals in Chestertown
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Chestertown Vacation Rentals with a Pool
Chestertown Vacation Rentals with Wi-Fi
Chestertown Pet-Friendly Vacation Rentals
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
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Vacation Rentals in Chestertown
Pick the perfect vacation rental for your trip at AllTheRooms.com. We aggregate Airbnb, Bed and Breakfast, Priceline and many more. Chestertown has 180 hotels, vacation rentals and other special places to stay, with prices to suit budget travelers, luxury travelers and everything in between. For those traveling on a budget, the cheapest place to stay in Chestertown is available at $49 per night. A typical rental in Chestertown costs on average $311 a night.
Those looking to get some work done during their trip to Chestertown can pick from 73 places to stay that include WiFi. 23 of our accommodations include a breakfast in the price. If you are driving to Chestertown, you'll want to pick from 70 places to stay that provide parking. We have 9 hotels and vacation rentals that have a pool or jacuzzi.
Those traveling with a cat, dog or some other animal can stay in any of 20 accommodations that are designated as pet-friendly.
107 of our rentals in Chestertown have been reviewed by previous guests. They rated 70% as great. 35 accommodations allow instant booking.