0 Bedrooms for 1 Guest
Price $10 - $1000+

53 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 4 rental sites including Booking.com, HomeAway, TripAdvisor, and more, ranging from $57 to $707 a night. 

    Information about Chestertown

    Vacation Rentals in Chestertown

    Find the best Chestertown vacation rentals with Tripping.com. Choose from 53 rentals, from studio apartments to luxurious condos to entire cabin homes. Book in advance or book instantly with properties marked as “Instabook,” with prices ranging from $57 a night to $707 a night.

    Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? 15 of homes in Chestertown offer high-speed wifi internet so you won’t miss a beat. Travelling with kids? Have them splash around in any of the 5 rentals with pool or jacuzzi, or relax with the family in one of the 46 homes with cable TV.

    For all those dog lovers and cat lovers, Chestertown offers 10 pet-friendly vacation rentals at an affordable price. Book the perfect vacation home that best matches your budget and accommodation style. For the ultimate stay, check out our listings now to grab the latest deals.

    Search properties from 4 rental sites in Chestertown where the top providers in that area are Booking.com, HomeAway, and TripAdvisor. There are 28 Booking.com rentals, 17 HomeAway short term rentals and 5 TripAdvisor vacation rentals.