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

Dog Friendly Hotels in Chestertown

59 HOTELS IN AND AROUND CHESTERTOWNRanking can be influenced by the commissions we receive.
Comfort Inn & Suites Chestertown main photo
Comfort Inn & Suites Chestertown
Hotel in Chestertown MDUS flag
8.2
Very Good
From $102
$
+10
Info
Categories
Dog Friendly
Honeymoon
Pool
Outdoor Pool
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
$
+3
Info
Categories
Dog Friendly
Free Wi-Fi
Parking
Pet-Friendly Home on Chester River w/ Dock! main photo
Pet-Friendly Home on Chester River w/ Dock!
Vacation Home in Chestertown MDUS flag
$
+5
Info
Categories
Dog Friendly
Pool
Outdoor Pool
Free Wi-Fi
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
Walk to Historic Chestertown: Dog-Friendly Retreat main photo
Walk to Historic Chestertown: Dog-Friendly Retreat
Vacation Home in Chestertown MDUS flag
$
+3
Info
Categories
Dog Friendly
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
14 more hotels nearby!
Thornton main photo
Thornton
3.6 mi from Chestertown
Vacation Home in Kennedyville MDUS flag
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
$
+2
Info
Categories
Dog Friendly
Free Wi-Fi
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
$
+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
$
+3
Info
Categories
Dog Friendly
Free Wi-Fi
Parking
Chesapeake Bay Retreat WBreathtaking Views main photo
Chesapeake Bay Retreat WBreathtaking Views
11.1 mi from Chestertown
Vacation Home in Rock Hall MDUS flag
9.0
Excellent
$
+3
Info
Categories
Dog Friendly
Free Wi-Fi
Parking
Family-Friendly Cottage, Walk to the Beach! main photo
Family-Friendly Cottage, Walk to the Beach!
11.1 mi from Chestertown
Vacation Home in Kennedyville MDUS flag
10
Excellent
Currently inactive on our platform.
$
+3
Info
Categories
Dog Friendly
Free Wi-Fi
Parking
Bayside cottage steps from the harbor main photo
Bayside cottage steps from the harbor
11.2 mi from Chestertown
Vacation Home in Rock Hall MDUS flag
5.0
Rated
Currently inactive on our platform.
$
+3
Info
Categories
Dog Friendly
Free Wi-Fi
Parking
Mariners Motel main photo
Mariners Motel
11.2 mi from Chestertown
Accommodation in Rock Hall MDUS flag
9.2
Excellent
From $160
$
+5
Info
Categories
Dog Friendly
Pool
Outdoor Pool
Free Wi-Fi
Blake House Historic Estate with Private Inn main photo
Blake House Historic Estate with Private Inn
11.5 mi from Chestertown
Villa in Centreville MDUS flag
10
Excellent
From $1,619
$
+6
Info
Categories
Dog Friendly
Pool
Private Pool
Outdoor Pool
Free Wi-Fi
Centreville Waterfront Farm - 170 Acres - Pool - Private Dock - Private Beach main photo
Centreville Waterfront Farm - 170 Acres - Pool - Private Dock - Private Beach
12.7 mi from Chestertown
Vacation Home in Centreville MDUS flag
$
+5
Info
Categories
Dog Friendly
Pool
Outdoor Pool
Free Wi-Fi
Gorgeous Creek Side Ranch-Style Estate With Dock main photo
Gorgeous Creek Side Ranch-Style Estate With Dock
18.6 mi from Chestertown
Vacation Home in Grasonville MDUS flag
$
+4
Info
Categories
Dog Friendly
Free Wi-Fi
Parking
Veazey Cove Coastal Lodge BAYFRONT with POOL and DOCK main photo
Veazey Cove Coastal Lodge BAYFRONT with POOL and DOCK
18.8 mi from Chestertown
Vacation Home in Earleville MDUS flag
$
+4
Info
Categories
Dog Friendly
Pool
Outdoor Pool
Free Wi-Fi
Waterfront Home with Private Beach, Stunning Views main photo
Waterfront Home with Private Beach, Stunning Views
18.8 mi from Chestertown
Vacation Home in Middle River MDUS flag
10
Excellent
From $788
$
+3
Info
Categories
Dog Friendly
Free Wi-Fi
Parking
Holiday Inn Express Annapolis East-Kent Island by IHG main photo
Holiday Inn Express Annapolis East-Kent Island by IHG
19.7 mi from Chestertown
Resort in Grasonville MDUS flag
9.2
Excellent
From $118
$
+9
Info
Categories
Dog Friendly
Golf
Family
*Additional taxes or fees may apply. Please check the final price before completing your booking.Showing 1-20 out of 59 hotels in and around Chestertown
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