Find the best vacation rental

ACCOMMODATION TYPES

Cheap Airbnb in Chestertown, MD: Top Deals

4.7 (22 reviews)
Brampton Bed and Breakfast Inn
Bed And Breakfast
$199 /night
View deal
4.8 (34 reviews)
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Guest Suite · 6 Guests · 2 Bedrooms
$520 /night*
View deal
4.9 (28 reviews)
Charming Chestertown Waterfront Cottage
Guest Suite · 6 Guests · 3 Bedrooms
$406 /night*
View deal
5.0 (60 reviews)
Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
Guest Suite · 8 Guests · 4 Bedrooms
$522 /night*
View deal
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
House
$380 /night
View deal
4.9 (32 reviews)
350 Acre Waterfront Farm; High Speed Internet, Pool, Sport Court & Private Dock
Guest Suite · 2 Guests · 4 Bedrooms
$726 /night*
View deal
4.9 (15 reviews)
River Lodge, Casual Riverfront setting
Lodge · 10 Guests · 4 Bedrooms
$824 /night*
View deal
4.9 (10 reviews)
Manor House on Beautiful Eastern Shore Estate
Guest Suite · 2 Guests · 6 Bedrooms
$1423 /night*
View deal
Red Roof Inn & Suites Chestertown
Hotel
$119 /night
View deal

Similar Inspirational Vacation Rental Destinations

Which Price Range Is Considered As A Good Deal in Chestertown, MD Area?
Vacation House & Apartment Rental Price Information in Chestertown, MD
+
The graph shows the percentages of vacation homes in each price bucket. Chestertown has the largest percentage (20.99%) of homes in $50 - $100 price range.
$0 to 50
$0 to 50
$50 to 100
$50 to 100
$100 to 150
$100 to 150
$150 to 200
$150 to 200
$200 to 250
$200 to 250
$250 to 300
$250 to 300
$300 to 350
$300 to 350
$350 to 400
$350 to 400
$400 to 450
$400 to 450
$450 to 500
$450 to 500
$500 +
$500 +
How Many Accommodations Are Pets Allowed in Chestertown, MD?
Percentage of Pet Friendly Rental Properties in Chestertown, MD
+
25.77% of vacation homes in Chestertown are pet friendly. If you have pet allergies, make sure to check the home property and see whether it is a pet-friendly vacation home or not.
Best Tourist Attractions in Chestertown, MD?
Top Rated Places to Visit in Chestertown, MD
+
How Many Airports in Chestertown, MD?
Top Airports in Chestertown, MD
+

Here are the airports that located near Chestertown:

* The displayed nightly rate may be estimated based on a future travel date. Narrow down your search with checkin and checkout dates to see the exact price.
See all offers