Chestertown, MD Vacation Rentals

Our Favorite Vacation Rentals in Chestertown

  • 104 Chesapeake House Condo
     Home/Apartment
    Booking.com
    From
    $292
  • Belle Rose Cottage at Victory Farm (Pet Friendly!)
    ExcellentHome/Apartment
    HolidayLettings
    From
    $209
  • Chester River House with Views
    Good3br Home/Apartment
    HolidayLettings
    From
    $166
  • Retreat at a quiet, water front cottage
    Good3br Home/Apartment
    HolidayLettings
    From
    $427
  • Sailors Crossing
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $505
  • Cottage On Kent
    ExcellentCottage
    HolidayLettings
    From
    $245
  • Bay Cottage
     2br Home/Apartment
    HolidayLettings
    From
    $354
  • Bayside Retreat
     3br Home/Apartment
    HolidayLettings
    From
    $380

Check prices for these upcoming dates

Chestertown Vacation Rentals with a Pool

  • Piney Grove Farm
    Excellent5br Farm Stay
    Airbnb
    From
    $650
  • Chestertown Watson Family Farm
    Excellent5br Home/Apartment
    Airbnb
    From
    $678
  • 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

  • Cozy Airstream on a beautiful horse farm
    ExcellentHome/Apartment
    Airbnb
    From
    $112
  • Historic Chestertown
    Excellent3br Home/Apartment
    Airbnb
    From
    $367
  • RIVER WATCH
    Excellent3br Home/Apartment
    Airbnb
    From
    $237
  • Rivershore Retreat
    Excellent2br Home/Apartment
    Airbnb
    From
    $333

Chestertown Pet-Friendly Vacation Rentals

  • River Lodge
    Excellent4br Home/Apartment
    Airbnb
    From
    $757
  • ★Beautiful Waterfront Chestertown Getaway
    ExcellentHome/Apartment
    Airbnb
    From
    $134
  • Entire River Front Home - 4 Bedrooms 4.5 Baths
    Excellent4br Home/Apartment
    Airbnb
    From
    $636
  • Egret's Nest, A Waterfront Oasis near Rock Hall
     Home/Apartment
    Airbnb
    From
    $367

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
Most availability
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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
64°
3
63° 11°
3
74° 21°
4
80° 32°
3
92° 46°
4
93° 50°
5
98° 62°
3
95° 60°
2
93° 46°
1
95° 38°
5
67° 20°
2
68° 18°
5
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
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.

What Expert Travelers Think

  • — I love AllTheRooms because it is not only local homes for renting, and not only hotels, but everything combined. When I am about to book a place to stay, I usually spend a couple of hours looking through both hotel sites and local home sites, comparing the prices and places.

    Alli Sims
    Alli SimsAlli Sims
  • — I love AllTheRooms because it enables me to compare a range of providers in just one search. I'd normally spend time checking prices across a range of platforms by visiting different websites one-by-one, so this helps me to save time on my accommodation searches while planning my upcoming trips

    Kacie Morgan
    Kacie MorganThe Rare Welsh Bit
  • — When I plan a trip, I no longer waste time visiting multiple websites in search of the best accommodations. Now, I just go to AllTheRooms and immediately find everything from luxury villas to pet-friendly rentals! All in one place

    Whitney Wear
    Whitney WearTravel Better Guide

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