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

Hotels in Chestertown

191 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
9.1
Excellent
From $332
$
+5
Info
Categories
Small
Parking
EV charging stations
Boutique-Style
Comfort Inn & Suites Chestertown main photo
Comfort Inn & Suites Chestertown
Hotel in Chestertown MDUS flag
8.2
Very Good
$
+11
Info
Categories
Golf
Honeymoon
Dog Friendly
Driftwood Inn main photo
Driftwood Inn
Motel in Chestertown MDUS flag
5.9
Rated
From $69
$
+3
Info
Categories
Free Wi-Fi
Parking
Small
Carriage House Hideaway In Center of Chestertown main photo
Carriage House Hideaway In Center of Chestertown
Apartment in Chestertown MDUS flag
9.8
Excellent
Currently inactive on our platform.
$
+1
Info
Categories
Dog Friendly
Pet-Friendly Home on Chester River w/ Dock! main photo
Pet-Friendly Home on Chester River w/ Dock!
Vacation Home in Chestertown MDUS flag
0.0
$
+5
Info
Categories
Dog Friendly
Pool
Outdoor Pool
Free Wi-Fi
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
Currently inactive on our platform.
$
+3
Info
Categories
Dog Friendly
Free Wi-Fi
Parking
Waterfront Millington Vacation Rental w/ Hot Tub! main photo
Waterfront Millington Vacation Rental w/ Hot Tub!
Vacation Home in Chestertown MDUS flag
0.0
$
+2
Info
Categories
Free Wi-Fi
Parking
River Heights Retreat main photo
River Heights Retreat
Vacation Home in Chestertown MDUS flag
10
Excellent
$
+2
Info
Categories
Dog Friendly
Free Wi-Fi
Walk to Historic Chestertown: Dog-Friendly Retreat main photo
Walk to Historic Chestertown: Dog-Friendly Retreat
Vacation Home in Chestertown MDUS flag
0.0
$
+3
Info
Categories
Dog Friendly
Free Wi-Fi
Parking
3 Mi to Washington College! Updated Home w/ Patio main photo
3 Mi to Washington College! Updated Home w/ Patio
Vacation Home in Chestertown MDUS flag
0.0
$
+2
Info
Categories
Free Wi-Fi
Parking
Porterhouse Farm main photo
Porterhouse Farm
Vacation Home in Chestertown MDUS flag
0.0
$
+4
Info
Categories
Pool
Outdoor Pool
Free Wi-Fi
Parking
Old Bridge main photo
Old Bridge
Villa in Chestertown MDUS flag
0.0
Currently inactive on our platform.
$
+3
Info
Categories
Parking
EV charging stations
Free Wi-Fi
Millington Manor main photo
Millington Manor
Bed & Breakfast in Chestertown MDUS flag
0.0
Currently inactive on our platform.
$
+2
Info
Categories
Parking
Small
7 more hotels nearby!
Thornton main photo
Thornton
3.6 mi from Chestertown
Vacation Home in Kennedyville MDUS flag
0.0
Currently inactive on our platform.
$
+4
Info
Categories
Dog Friendly
Pool
Free Wi-Fi
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
$
+2
Info
Categories
Dog Friendly
Free Wi-Fi
The Still Pond Inn main photo
The Still Pond Inn
9.2 mi from Chestertown
Apartment in Kennedyville MDUS flag
9.8
Excellent
$
+2
Info
Categories
Free Wi-Fi
Parking
Twin Ponds Lodge main photo
Twin Ponds Lodge
10.6 mi from Chestertown
Vacation Home in Centreville MDUS flag
0.0
Currently inactive on our platform.
$
Info
Waterfront Private Dock Boat Tie-Up & Near Town main photo
Waterfront Private Dock Boat Tie-Up & Near Town
10.7 mi from Chestertown
Vacation Home in Rock Hall MDUS flag
0.0
$
+3
Info
Categories
Dog Friendly
Free Wi-Fi
Parking
Grays Inn Creek Waterfront Pvt Dock Kayaks & View main photo
Grays Inn Creek Waterfront Pvt Dock Kayaks & View
10.7 mi from Chestertown
Vacation Home in Rock Hall MDUS flag
0.0
$
+3
Info
Categories
Dog Friendly
Free Wi-Fi
Parking
Rock Hall Retreat w/ Balcony Near Park & Marina! main photo
Rock Hall Retreat w/ Balcony Near Park & Marina!
10.8 mi from Chestertown
Vacation Home in Rock Hall MDUS flag
9.7
Excellent
$
+2
Info
Categories
Free Wi-Fi
Parking
*Additional taxes or fees may apply. Please check the final price before completing your booking.Showing 1-20 out of 191 hotels in and around Chestertown
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