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  1. World
  2. >North America
  3. >United States
  4. >Maryland
  5. >Kent
  6. >Chestertown

Hotels in Chestertown

200+ HOTELS IN AND AROUND CHESTERTOWNRanking can be influenced by the commissions we receive.
Brampton 1860 main photo
Brampton 1860
Bed & Breakfast in Chestertown MDUS flag
9.6
Excellent
From $334
$
Info
Categories
Small
Parking
EV charging stations
Boutique-Style
Lodging at The Imperial main photo
Lodging at The Imperial
Hotel in Chestertown MDUS flag
9.5
Excellent
$
Info
Categories
Family
Free Wi-Fi
Parking
Quality Suites main photo
Quality Suites
Hotel in Chestertown MDUS flag
0.0
$
Info
Categories
Pool
Free Wi-Fi
3 Star
Comfort Inn & Suites Chestertown main photo
Comfort Inn & Suites Chestertown
Hotel in Chestertown MDUS flag
8.2
Very Good
$
Info
Categories
Golf
Honeymoon
Dog Friendly
Driftwood Inn main photo
Driftwood Inn
Motel in Chestertown MDUS flag
4.1
Rated
From $69
$
Info
Categories
Dog Friendly
Wren Retweet main photo
Wren Retweet
Villa in Chestertown MDUS flag
0.0
$
Info
Categories
Dog Friendly
Carriage House Hideaway In Center of Chestertown main photo
Carriage House Hideaway In Center of Chestertown
Apartment in Chestertown MDUS flag
9.8
Excellent
$
Info
Categories
Dog Friendly
Pet-Friendly Home on Chester River with Dock! main photo
Pet-Friendly Home on Chester River with Dock!
Vacation Home in Chestertown MDUS flag
0.0
$
Info
Categories
Dog Friendly
Pool
Outdoor Pool
Free Wi-Fi
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town main photo
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Vacation Home in Chestertown MDUS flag
0.0
$
Info
Categories
Dog Friendly
Free Wi-Fi
Parking
Walk to the Beach with Deck, Fireplace, BBQ Grill, Boat Ramp & Office main photo
Walk to the Beach with Deck, Fireplace, BBQ Grill, Boat Ramp & Office
Vacation Home in Chestertown MDUS flag
10
Excellent
$
Info
Categories
Parking
Waterfront Millington Vacation Rental with Hot Tub! main photo
Waterfront Millington Vacation Rental with Hot Tub!
Vacation Home in Chestertown MDUS flag
0.0
$
Info
River Heights Retreat main photo
River Heights Retreat
Vacation Home in Chestertown MDUS flag
10
Excellent
$
Info
Categories
Dog Friendly
Walk to Historic Chestertown Dog-Friendly Retreat main photo
Walk to Historic Chestertown Dog-Friendly Retreat
Vacation Home in Chestertown MDUS flag
0.0
$
Info
Categories
Dog Friendly
Free Wi-Fi
Parking
3 Mi to Washington College! Updated Home with Patio main photo
3 Mi to Washington College! Updated Home with Patio
Vacation Home in Chestertown MDUS flag
0.0
$
Info
Categories
Dog Friendly
Free Wi-Fi
Parking
Porterhouse Farm main photo
Porterhouse Farm
Vacation Home in Chestertown MDUS flag
0.0
$
Info
Categories
Pool
Free Wi-Fi
Parking
Old Bridge main photo
Old Bridge
Villa in Chestertown MDUS flag
0.0
$
Info
Categories
Parking
EV charging stations
Free Wi-Fi
Millington Manor main photo
Millington Manor
Bed & Breakfast in Chestertown MDUS flag
0.0
$
Info
Categories
Parking
Small
3 more hotels nearby!
Thornton main photo
Thornton
3.6 mi from Chestertown
Vacation Home in Kennedyville MDUS flag
0.0
$
Info
Categories
Dog Friendly
Pool
Free Wi-Fi
Oakley Acre main photo
Oakley Acre
7.9 mi from Chestertown
Apartment in Kennedyville MDUS flag
0.0
$
Info
Categories
Free Wi-Fi
Parking
Bamboo Sands Villa and Captains Lookout main photo
Bamboo Sands Villa and Captains Lookout
8.6 mi from Chestertown
Vacation Home in Kennedyville MDUS flag
0.0
$
Info
Categories
Dog Friendly
Free Wi-Fi
*Additional taxes or fees may apply. Please check the final price before completing your booking.Showing 1-20 out of 200+ hotels in and around Chestertown
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