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Chestertown bed & breakfasts

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Best Chestertown bed & breakfasts

Most recommended Chestertown bed & breakfasts

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Brampton 1860 - Chestertown - Bedroom
Brampton 1860
Chestertown, MD
9.4Wonderful(37)
Parking
Free Wi-Fi
$409+
Check availability
Inn At Mitchell House - Chestertown
Inn At Mitchell House
Chestertown, MD
Free Wi-Fi
$166+
Check availability
Great Oak Manor - Chestertown
Great Oak Manor
Chestertown, MD
9.3Wonderful(63)
Free Wi-Fi
$165+
Check availability
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$0 - $77$77 - $154$154 - $231$231 - $307$307+ per night

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Free cancellationFree breakfastFree parkingFree internet

Good to know

Low season

March

High season

December

Average price (weeknight)

$310

Average price (weekend night)

$353
Cheapest month to stay with an average 32% drop in price.
Most expensive month to stay with an average 20% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Chestertown bed & breakfast deals

  • Bed & Breakfast room prices vary depending on many factors but you’ll likely find the best bed & breakfast deals in Chestertown if you stay on a Wednesday. The most expensive day for bed & breakfast bookings is Sunday.
  • 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 bed & breakfast.
  • Don’t know how much time you need to see all the sights? KAYAK users usually book their bed & breakfast in Washington, D.C. for 2 days.

FAQs when booking a bed & breakfast in Chestertown

  • What are the best bed & breakfasts near Chestertown Railroad Station?

    Chestertown Railroad Station is a popular area in Chestertown and there are many bed & breakfasts closeby. Check out Lauretum Inn Bed And Breakfast or Brampton 1860 for hostels recommended by KAYAK that are within walking distance of Chestertown Railroad Station.

  • Is it cheaper to stay in a bed & breakfast than in a hotel in Chestertown?

    The average price for a night in a bed & breakfast in Chestertown is $307 compared to $136 for a night in a hotel.

Where to find the best bed & breakfasts in Chestertown?

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

Everything you need to know for your stay in Chestertown

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

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