Secluded Cottage in Middle of Chestertown
Apartment in Chestertown MD
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4-Star Apartment

Dog Friendly Apartment

Apartment with Free Wi-Fi

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Wren Retweet
Villas in Chestertown MD
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4-Star Villas

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7 more hotels nearby!
Great Oak Manor 6.3 km from Chestertown
Bed & Breakfast in Great Oak Landing MD
9.3
Excellent
From $165
From $165
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4-Star Bed & Breakfast

Bed & Breakfast with Parking

EV charging stations  

Bed & Breakfast with Rooms With Fireplace

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Inn at Huntingfield Creek 10.0 km from Chestertown
Bed & Breakfast in Rock Hall MD
9.2
Excellent
From $250
From $250
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4-Star Bed & Breakfast

Luxury Bed & Breakfast

Bed & Breakfast with Swimming Pool

Outdoor Pool  

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Stunning 8 Bedroom Villa on the Chesapeake Bay 10.6 km from Chestertown
Villas in Rock Hall MD
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4-Star Villas

Villas near Golf Courses

Villas with Swimming Pool

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The Inn at Chesapeake Bay Beach Club 20.7 km from Chestertown
Hotel in Stevensville MD
9.3
Excellent
From $289
From $289
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4-Star Hotel

Hotel with Swimming Pool

Outdoor Pool  

Luxury Hotel

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Bayfront Annapolis Home with Private Boat Dock! 21.0 km from Chestertown
Vacation Home in Annapolis MD
9.7
Excellent
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4-Star Vacation Home

Dog Friendly Vacation Home

Vacation Home with Free Wi-Fi

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Apple House- New Townhouse - 2 Car Garage by CCBC & Franklin Sq 22.5 km from Chestertown
Vacation Home in Rosedale MD
10
Excellent
Info Categories
4-Star Vacation Home

Vacation Home with Free Wi-Fi

Vacation Home with Parking

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Chic & Cozy City Living Enjoy Baltimore in Style 24.0 km from Chestertown
Vacation Home in Baltimore MD
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4-Star Vacation Home

Family Friendly Vacation Home

Vacation Home with Free Wi-Fi

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*Additional taxes or fees may apply. Please check the final price before completing your booking.
View all hotels in Chestertown.
Categories:
  •     4 Star (9)
  •     Parking (8)
  •     Free Wi-Fi (6)
  •     Dog Friendly (4)
  •     Luxury (3)
  •     Pool (3)
  •     Yoga (2)
  •     Small (2)
  •     Outdoor Pool (2)
  •     Gym (2)
  •     Family (2)
  •     Adult Only (1)
  •     Honeymoon (1)
  •     Golf (1)
  •     Rooms with Fireplace (1)
  •     EV charging stations (1)
  •     Romantic (1)
  •     Business (1)
  •     Spa (1)
  •     Accessible (1)
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