Quality Suites
Hotel in Chestertown MD
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3-Star Hotel

Hotel with Swimming Pool

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Inn at Mitchell House
Bed & Breakfast in Chestertown MD
From $166
From $166
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3-Star Bed & Breakfast

Bed & Breakfast with Rooms With Fireplace

Bed & Breakfast with Free Wi-Fi

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51 more hotels nearby!
Cozy Eastern Shore Farmhouse Winter Getaway! 6.9 km from Chestertown
Vacation Home in Rock Hall MD
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3-Star Vacation Home

Vacation Home with Free Wi-Fi

Vacation Home with Parking

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Charming Chesapeake Bay Retreat with Stunning Views! 9.2 km from Chestertown
Vacation Home in Rock Hall MD
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3-Star Vacation Home

Vacation Home with Free Wi-Fi

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Blake House Historic Estate with Private Inn 11.4 km from Chestertown
Villas in Centreville MD
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3-Star Villas

Dog Friendly Villas

Villas with Swimming Pool

Outdoor Pool  

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Captain’s Quarters - unique home on Corsica River! 11.6 km from Chestertown
Vacation Home in Centreville MD
9.4
Excellent
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3-Star Vacation Home

Vacation Home near Golf Courses

Family Friendly Vacation Home

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Beautiful Middle River Retreat with Boat Dock! 16.6 km from Chestertown
Vacation Home in Middle River MD
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3-Star Vacation Home

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Gorgeous Creek Side Ranch-Style Estate With Dock 17.9 km from Chestertown
Vacation Home in Grasonville MD
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3-Star Vacation Home

Vacation Home with Free Wi-Fi

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Joppatowne Home with Private Deck and Fireplace! 18.0 km from Chestertown
Vacation Home in Edgewood MD
8.0
Very Good
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3-Star Vacation Home

Dog Friendly Vacation Home

Vacation Home with Free Wi-Fi

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Holiday Inn Express Annapolis East-Kent Island, an IHG Hotel 18.7 km from Chestertown
Resort in Grasonville MD
8.6
Very Good
From $153
From $153
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3-Star Resort

Resort near Golf Courses

Family Friendly Resort

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Best Western Kent Narrows Inn 18.8 km from Chestertown
Hotel in Grasonville MD
7.5
Good
From $122
From $122
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3-Star Hotel

Hotel with Rooms With Jacuzzi / Hot-tub

Hotel for Honeymoon

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Hilton Garden Inn Kent Island 18.9 km from Chestertown
Hotel in Grasonville MD
8.3
Very Good
From $210
From $210
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3-Star Hotel

Hotel Taking Steps Towards Sustainability

Hotel for Honeymoon

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Springhill Suites Baltimore White Marsh/Middle River 19.0 km from Chestertown
Hotel in Middle River MD
8.3
Very Good
From $161
From $161
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3-Star Hotel

Hotel for Honeymoon

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Home2 Suites by Hilton Baltimore/Aberdeen MD 19.4 km from Chestertown
Hotel in Aberdeen MD
8.0
Very Good
From $132
From $132
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3-Star Hotel

Hotel Taking Steps Towards Sustainability

Hotel for Honeymoon

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Hampton Inn & Suites Aberdeen/APG South 19.6 km from Chestertown
Hotel in Edgewood MD
8.8
Excellent
From $115
From $115
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3-Star Hotel

Hotel Taking Steps Towards Sustainability

Hotel for Honeymoon

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Homewood Suites by Hilton Bel Air 19.8 km from Chestertown
Hotel in Riverside MD
7.8
Good
From $142
From $142
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3-Star Hotel

Hotel Taking Steps Towards Sustainability

Hotel for Honeymoon

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Country Inn & Suites by Radisson, Bel Air-Aberdeen, MD 19.8 km from Chestertown
Hotel in Bel Air MD
8.3
Very Good
From $115
From $115
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3-Star Hotel

Hotel near Golf Courses

Hotel Taking Steps Towards Sustainability

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SpringHill Suites Edgewood Aberdeen 19.8 km from Chestertown
Hotel in Bel Air MD
8.3
Very Good
From $140
From $140
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3-Star Hotel

Hotel Taking Steps Towards Sustainability

Hotel for Honeymoon

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Bay Side Inn & Suites 19.9 km from Chestertown
Hotel in Aberdeen MD
5.4
Rated
From $78
From $78
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3-Star Hotel

Hotel for Honeymoon

Hotel with Free Wi-Fi

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Highlands Cottage Upscale Getaway with Yard! 20.5 km from Chestertown
Vacation Home in Middle River MD
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3-Star 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:
  •     3 Star (53)
  •     Parking (34)
  •     Free Wi-Fi (26)
  •     Family (22)
  •     Pool (22)
  •     Honeymoon (21)
  •     Accessible (21)
  •     Business (21)
  •     Gym (21)
  •     Dog Friendly (18)
  •     Sustainability Journey (13)
  •     Indoor Pool (10)
  •     Outdoor Pool (10)
  •     Golf (4)
  •     Small (4)
  •     Heated Pool (3)
  •     EV charging stations (2)
  •     Rooms with Fireplace (1)
  •     Adult Only (1)
  •     Rooms with Jacuzzi / Hot-Tub (1)
  •     Tennis (1)
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