5 Chestertown Vacation Rentals & Short Term Rentals

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Compare Chestertown vacation rentals from 4 rental sites including HomeAway, TripAdvisor, Booking.com and more, ranging from $94 to $1114 a night.
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Information about Chestertown

Vacation Rentals in Chestertown

Find the best Chestertown vacation rentals with Tripping.com. Choose from 197 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 $94 a night to $1114 a night.

Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? 133 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 11 rentals with pool or jacuzzi, or relax with the family in one of the 160 homes with cable TV.

For all those dog lovers and cat lovers, Chestertown offers 42 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 HomeAway, TripAdvisor, and Booking.com. There are 117 HomeAway rentals, 49 TripAdvisor short term rentals and 28 Booking.com vacation rentals.
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