20 Chestertown Holiday Rentals

Tripping.com is the world's top vacation rental search engine, rated 9.6 out of 10 based on 50 user reviews.
Compare Chestertown holiday rentals from 5 rental sites including HomeAway, Booking.com, TripAdvisor and more, from $67 a night.
Tip: You can see more results by expanding your search area, or changing some filters.

Information about Chestertown

Vacation Rentals in Chestertown

Looking for a vacation rental in Chestertown? Tripping.com has 20 rental homes available in Chestertown. Potential renters will find 0 studios, 5 1-bedroom, 4 2-bedroom and 11 rentals with 3 or more bedrooms from $67 a night. Many of these properties are instantly bookable.

The average price of a nightly rental in Chestertown is $250 while the average price of a weekly rental is $425. For those looking for more than a short term rental such as corporate rentals, extended stays or long term rentals, the average monthly price of a Chestertown home is $1620.

Wondering if you can bring your favorite dog or cat with you? We have 9 pet friendly vacation rentals available for you. In addition to accommodating pets, Chestertown rentals offer a variety of amenities. In particular, 18 rentals have internet and wifi, 16 have TV and/or cable and 1 have a pool or hot tub.

Search properties from 5 rental sites in Chestertown where the top providers in that area are HomeAway, Booking.com, and TripAdvisor. There are 14 HomeAway rentals, 2 Booking.com short term rentals and 2 TripAdvisor vacation rentals.