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Chestertown, MD Vacation Rentals

Our Favorite Vacation Rentals in Chestertown

See all 167 vacation rentals in Chestertown

Chestertown Vacation Rentals with a Pool

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Chestertown Vacation Rentals with Wi-Fi

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Chestertown Pet-Friendly 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 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 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 Weather in Chestertown

89º 44º
8.2
94º 54º
2.6
97º 55º
4.17
95º 60º
2.36
92º 56º
5
86º 35º
2.75
74º 20º
4.47
64º 22º
3.51
66º
3.44
74º 18º
4.52
73º 27º
3.37
82º 32º
2.58
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Rainy days
This climate histogram shows you the weather patterns in Chestertown. The hottest month in Chestertown is June, when temperatures peak at 97 ˚F. The coolest month is January, when temperatures drop to 2 ˚F. The wettest month in Chestertown is May with 8.2 inches of rain, while the driest month is August with 2.36 inches of rain.

What Expert Travelers Think

Vacation Rentals in Chestertown

Browse places to stay from all the leading providers including Airbnb, VRBO, Homeaway and many more at AllTheRooms.com. We have 167 vacation rentals, hotels and other accommodation types in Chestertown ranging from low-cost options to luxury places to stay. A trip to Chestertown can be affordable - our lowest price vacation rental is available at $55 per night. A typical accommodation in Chestertown costs on average $308 per night.

Those needing to get some work done during their trip to Chestertown can pick from 74 places to stay that provide WiFi. 17 places to stay include a morning meal. You can keep up with your workout regime by staying at one of 4 accommodations that provide gym facilities. If you are driving to Chestertown, you'll want to pick from 69 places to stay that provide parking. 8 vacation rentals come with a pool or jacuzzi

AllTheRooms has 21 pet-friendly places to stay in Chestertown, so if you're traveling with your cat or dog you won't have any trouble.

In Chestertown AllTheRooms currently aggregates hotels, vacation rentals, hostels from more than 5 providers, including 57 places to stay from Airbnb, 3 accommodations from VRBO and 3 places to stay from Homeaway.

99 of our accommodations in Chestertown have been reviewed and rated. 67% are rated excellent or good. 32 places to stay in are instantly bookable.