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Chestertown, MD Vacation Rentals

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Our Favorite Vacation Rentals in Chestertown

  • Belle Rose Cottage at Victory Farm (Pet Friendly!)
    Belle Rose Cottage at Victory Farm (Pet Friendly!)
    Excellent1br Home/Apartment
    HolidayLettingsFrom $209
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  • Cozy Apartment in Chestertown
    Cozy Apartment in Chestertown
    Excellent1br Home/Apartment
    HolidayLettingsFrom $134
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  • Big BD in Civil War House starting at 55$/night
    Big BD in Civil War House starting at 55$/night
    Good1br Home/Apartment
    HolidayLettingsFrom $86
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  • Cottage On Kent
    Cottage On Kent
    Excellent1br Cottage
    HolidayLettingsFrom $245
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  • Cozy Airstream on a beautiful horse farm
    Cozy Airstream on a beautiful horse farm
    Excellent1br Home/Apartment
    AirbnbFrom $122
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  • Quiet Cottage on Heron Pond
    Quiet Cottage on Heron Pond
    Excellent2br Home/Apartment
    AirbnbFrom $196
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  • Chestertown home with private inground pool
    Chestertown home with private inground pool
    Excellent3br Home/Apartment
    AirbnbFrom $417
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  • Stepne Manor
    Stepne Manor
    Excellent5br Home/Apartment
    AirbnbFrom $1094
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See all 154 deals in Chestertown

Chestertown Vacation Rentals with a Pool

  • Piney Grove Farm
    Piney Grove Farm
    Excellent5br Farm Stay
    AirbnbFrom $523
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  • Water View Condo with pool use in Rock Hall Harbor
    Water View Condo with pool use in Rock Hall Harbor
     2br Home/Apartment
    AirbnbFrom $392
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See all deals in Chestertown with a pool

Chestertown Vacation Rentals with Wi-Fi

  • Farm House w/ Water Access (near Chestertown)
    Farm House w/ Water Access (near Chestertown)
    Excellent4br Farmhouse
    AirbnbFrom $536
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  • Private Bedroom and bath in Chestertown, MD
    Private Bedroom and bath in Chestertown, MD
    Excellent1br Farm Stay
    AirbnbFrom $73
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  • Cottage by the Bay in Rock Hall, MD
    Cottage by the Bay in Rock Hall, MD
    Excellent3br Cottage
    AirbnbFrom $305
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  • Unique modern apartment with a view
    Unique modern apartment with a view
    Excellent1br Home/Apartment
    AirbnbFrom $366
    View Deal
See all deals in Chestertown with WiFis

Chestertown Pet-Friendly Vacation Rentals

  • River Lodge
    River Lodge
    Excellent4br Home/Apartment
    AirbnbFrom $724
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  • Running Fox
    Running Fox
    Excellent4br Home/Apartment
    AirbnbFrom $720
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  • Pet Friendly Guest Cottage with pool and dock
    Pet Friendly Guest Cottage with pool and dock
    Excellent3br Home/Apartment
    AirbnbFrom $440
    View Deal
  • Nautical Cottage
    Nautical Cottage
    Excellent3br Cottage
    AirbnbFrom $325
    View Deal
See all deals in Chestertown that allow pets

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

Most expensive
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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

97º 55º
4.17
95º 60º
2.36
92º 56º
5
86º 35º
2.75
74º 20º
4.47
64º 22º
3.51
66º 2º
3.44
74º 18º
4.52
73º 27º
3.37
82º 32º
2.58
89º 44º
8.2
94º 54º
2.6
Jul
Aug
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Rainy days
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 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 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.

Destinations near Chestertown