Romantic Hotels in Chestertown, Maryland

#1.

Holiday Inn Express Hotel & Suites Chestertown

150 Scheeler Road, 21620 Chestertown, Maryland

Holiday Inn Express Hotel & Suites Chestertown
Hotel Class
4.5
User Rating (3 sources) ×
  • It was perfect for our needs- quiet but with the pool it made it feel like a little vacation for us. more on PriceLine.com
  • The new and exciting Holiday Inn Express Hotel & Suites Chestertown is located off Rt. 213 Within walki... more on Orbitz
 

#2.

Comfort Suites Chestertown

160 Scheeler Road, Chestertown, MD 21620

Comfort Suites Chestertown
Hotel Class
4.0
User Rating (6 sources) ×
  • Needless to say it was immaculate and... more on Orbitz
  • For a one start hotel, it was clean and located near many restaurant options. more on MyTravelGuide
 

#3.

The Inn at Mitchell House

8796 Maryland Pkwy., Chestertown, Maryland

The Inn at Mitchell House
3.0
User Rating (2 sources) ×
  • They opened up their immaculate home to travelers like you are friends. more on TripAdvisor
  • Overview If you're looking for a quiet Old World retreat surrounded by remote farmland and habitats ... more on Frommers
 

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#4.

Imperial Hotel

208 High Street, Chestertown, Maryland

Imperial Hotel
3.0
User Rating (2 sources) ×
  • The food is always excellently prepared and presented. more on Yahoo! Travel
  • Overview How large of a hotel is Imperial Hotel? It's tiny--with 13 rooms. Summing up more than 15 attitudes and opi...
 

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#5.

Driftwood Inn

609 Washington Avenue, Chestertown, Maryland

Driftwood Inn
3.5
User Rating (2 sources) ×
 

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#6.

Brampton Bed & Breakfast Inn

25227 Chestertown Road, 21620 Chestertown, Maryland

Brampton Bed & Breakfast Inn
Hotel Class
3.5
User Rating (5 sources) ×
  • Our wedding cake was the best cake I 've ever eaten! more on BedAndBreakfast.com
  • Wonderful property, great food, relaxing front porch, huge room with fireplace, comfortable bed, luxurious ... more on igougo
 

#7.

Great Oak Manor

10568 Cliff Rd, Chestertown, MD 21620

Great Oak Manor
4.5
User Rating (4 sources) ×
  • Overview Awaken to the sounds of nature, wander down the Grand Staircase to the Waterfront and sit by... more on AnglerWeb.com
  • Overview Evening port and sherry are served in the Music Room, which is furnished with a piano, fine ... more on Hotels.com
 

#8.

Widow's Walk Inn

402 High St., Chestertown, Maryland

Widow's Walk Inn
3.0
User Rating (1 sources) ×
  • A first-floor room with private bathroom is spacious, with big... more on Frommers
  • Overview In the middle of all that Colonial grandeur sits this Victorian lady, an 1877 beauty with f... more on Frommers
 

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#9.

The Parker House

108 Spring Ave, Chestertown, Maryland

The Parker House
 

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