Chestertown, MD Vacation Rentals

Our Favorite Vacation Rentals in Chestertown

  • 104 Chesapeake House Condo
     Home/Apartment
    Booking.com
    From
    $357
  • Cozy & Spacious Chestertown Home
    Excellent4br Home/Apartment
    HolidayLettings
    From
    $358
  • Belle Rose Cottage at Victory Farm (Pet Friendly!)
    ExcellentHome/Apartment
    HolidayLettings
    From
    $209
  • Sailors Crossing
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $505
  • Cottage On Kent
    ExcellentCottage
    HolidayLettings
    From
    $245
  • Summer House in Rock Hall
     3br Home/Apartment
    HolidayLettings
    From
    $338
  • Bayside Retreat
     3br Home/Apartment
    HolidayLettings
    From
    $365
  • Cozy Airstream on a beautiful horse farm
    ExcellentHome/Apartment
    Airbnb
    From
    $112

Check prices for these upcoming dates

Chestertown Vacation Rentals with a Pool

  • Piney Grove Farm
    Excellent5br Farm Stay
    Airbnb
    From
    $650
  • Creek Cottage
    Excellent4br Home/Apartment
    Airbnb
    From
    $1,015
  • Water View Condo with pool use in Rock Hall Harbor
    Excellent2br Home/Apartment
    Airbnb
    From
    $387

Chestertown Vacation Rentals with Wi-Fi

  • Historic Chestertown
    Excellent3br Home/Apartment
    Airbnb
    From
    $367
  • River Lodge
    Excellent4br Home/Apartment
    Airbnb
    From
    $757
  • Running Fox
    Excellent4br Home/Apartment
    Airbnb
    From
    $754
  • very peaceful location (entire place to yourself!)
    Good4br Home/Apartment
    Airbnb
    From
    $325

Chestertown Pet-Friendly Vacation Rentals

  • Entire River Front Home - 4 Bedrooms 4.5 Baths
    Excellent4br Home/Apartment
    Airbnb
    From
    $636
  • Enjoy 8 acres of woods of your AirBnB
    Okay3br Home/Apartment
    Airbnb
    From
    $212
  • Egret's Nest, A Waterfront Oasis near Rock Hall
     Home/Apartment
    Airbnb
    From
    $367
  • Nautical Cottage
    Excellent3br Cottage
    Airbnb
    From
    $328

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 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
74° 20°
4
64° 22°
4
66°
3
74° 18°
5
73° 27°
3
82° 32°
3
89° 44°
8
94° 54°
3
97° 55°
4
95° 60°
2
92° 56°
5
86° 35°
3
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
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 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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    Laurelle McVickerLaurelle McVicker
  • — When I first opened up the AllTheRooms.com site, I was impressed right away... When I’m traveling, I don’t like to waste time searching multiple engines for accommodations, it gets overwhelming and frustrating fast. I want a unique, comfortable stay for the best deal

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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.

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