19 Chestertown Vacation Rentals & Short Term 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 vacation rentals from 5 rental sites including Booking.com, HomeAway, TripAdvisor and more, ranging from $57 to $707 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 56 rental homes available in Chestertown. Potential renters will find studios, 36 1-bedroom, 3 2-bedroom and 17 rentals with 3 or more bedrooms ranging from $57 a night to $707 a night. Many of these properties are instantly bookable.

The average price of a nightly rental in Chestertown is $262 while the average price of a weekly rental is $2863. 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 $2610.

Wondering if you can bring your favorite dog or cat with you? We have 10 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, 19 have TV and/or cable and 4 have a pool or hot tub.

Search properties from 5 rental sites in Chestertown where the top providers in that area are Booking.com, HomeAway, and TripAdvisor. There are 28 Booking.com rentals, 18 HomeAway short term rentals and 6 TripAdvisor vacation rentals.
How likely would you be to recommend Tripping.com to a friend?
Not At All
  • 0
  • 1
  • 2
  • 3
  • 4
  • 5
  • 6
  • 7
  • 8
  • 9
  • 10
Extremely Likely
Thank you for your response!
Why?