Chestertown, MD Vacation Rentals

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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.

Price and Availability in Chestertown

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The cheapest day to stay at a vacation rental in Chestertown tends to be Tuesday, while the most expensive day tends to be Sunday. Vacation homes in Chestertown tend to be busiest on Saturdays, while it tends to be much quieter on Mondays.
The most expensive month to stay in a vacation rental in Chestertown is in July, while the cheapest month is in January. The most popular time to book a vacation rental in Chestertown is in the high season in July. Chestertown has its low season in December, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Chestertown

Rainy days
98° 62°
3
95° 60°
2
93° 46°
1
95° 38°
5
67° 20°
2
68° 18°
5
64°
3
63° 11°
3
74° 21°
4
80° 32°
3
92° 46°
4
93° 50°
5
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Rainy days

This climate histogram shows you the weather patterns in Chestertown. The warmest months in Chestertown are June and March, when temperatures reach 98 ˚F. The coolest month is December, when temperatures drop to 9 ˚F. The wettest month in Chestertown is January with 5.25 inches of rain, while the driest month is April with 0.83 inches of rain.

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