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Chestertown motels

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Best Chestertown motels

Most recommended Chestertown motels

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Driftwood Inn - Chestertown - Bedroom
Driftwood Inn
Chestertown, MD
5.0Fair(162)
Parking
Free Wi-Fi
Pet friendly
$69+
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How much is a Chestertown motel?

Here are our most popular & best value motels

2 stars and below

Good to know

Low season

April

High season

October

Average price (weeknight)

$69
Cheapest month to stay with an average 1% drop in price.
Most expensive month to stay with an average 2% rise in price.
Average Sun - Thu price over the last 2 weeks.

KAYAK's top tips for finding Chestertown motel deals

  • If you’re looking for a cheap motel in Chestertown, you should consider going during the low season. You’ll generally find lower-priced motels in Chestertown in April and November.
  • Motel room prices vary depending on many factors but you’ll likely find the best motel deals in Chestertown if you stay on a Monday. The most expensive day for motel bookings is Wednesday.
  • If you want to ensure you grab a bargain, try to book more than 90 days before your stay to get the best price for a Chestertown motel.
  • Don’t know how much time you need to see all the sights? KAYAK users usually book their motel in Washington, D.C. for 1 day.
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Where to find the best motels in Chestertown?

Our map will help you find the perfect motel in Chestertown by showing you the exact location of each motel.

Everything you need to know for your stay in Chestertown

Chestertown motel deals. Search for motels in Chestertown. Find cheap motels in Chestertown. KAYAK searches hundreds of travel sites to help you find cheap motels and book the room that suits you best.

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