We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Chestertown

Refine search

Price per night

 

Traveler rating

 

Hotel class

 

Hotel brand

Show all brands
Major Brands
Individual Chains
Show only major brands
 

Property name

Reset
 
Free Newsletter

Interested in Chestertown?

We'll send you updates with the latest deals, reviews and articles for Chestertown each week.

Map of Chestertown Hotels

Hotels (2)

B&Bs / Inns (12)

Specialty Lodging (0)

You are zoomed out too far to see location pins. Please zoom back in.
Search hotels
Map showing X-Y of Z
Clear filter(s)

Hotels Travelers Trust

Sort by [ Popularity ] [ Price ]
208 Mount Vernon Ave, Chestertown, MD
$99 - $139 Avg. price/night*
Ollie #1 of 12 B&Bs / Inns in Chestertown
  •  Wow..says it all 
  • I am not even sure where to begin...This home is a home away from home... more
  • January 25, 2015
Traveler photos (18)
25227 Chestertown Road, Chestertown, MD 21620
Brampton Bed and Breakfast Inn Slideshow
Show Prices
$232 - $279 Avg. price/night*
Ollie #2 of 12 B&Bs / Inns in Chestertown
Professional photos | Traveler photos (101)
Offers & Announcements 3 for 2, ends March 31
8796 Maryland Pkwy., Chestertown, MD 21620
The Inn at Mitchell House Slideshow
$109 - $239 Avg. price/night*
Ollie #3 of 12 B&Bs / Inns in Chestertown
  •  Knitting Weekend Fun! 
  • Nine of us were here for a knitting weekend. A couple of the attendees had... more
  • March 17, 2015
Traveler photos (26)
402 High St., Chestertown, MD 21620
No photo provided
$30 - $135 Avg. price/night*
Ollie #4 of 12 B&Bs / Inns in Chestertown
  •  Great B&B! 
  • Lovely place. Very clean and comfortable. Robert, our host, was very nice... more
  • November 15, 2014
114 Washington Ave, Chestertown, MD
Show Prices
$154 - $204 Avg. price/night*
Ollie #5 of 12 B&Bs / Inns in Chestertown
  •  Girl Friend Getaway 
  • My friend and I recently snuck out of town to get some much needed R&R... more
  • January 14, 2015
Professional photos | Traveler photos (1)
10568 Cliff Rd, Chestertown, MD 21620
$209 - $220 Avg. price/night*
Ollie #6 of 12 B&Bs / Inns in Chestertown
  •  Under new management 
  • We arrived to find to our surprise that our visit coincided with the first... more
  • February 28, 2015
Traveler photos (68)
231 High St, Chestertown, MD 21620
$30 - $180 Avg. price/night*
Ollie #7 of 12 B&Bs / Inns in Chestertown
  •  Elegant Swan 
  • Chestertown is a lovely town and we thought The White Swan a very... more
  • November 9, 2014
Traveler photos (2)
150 Scheeler Road, Chestertown, MD 21620
Holiday Inn Express Hotel & Suites Chestertown Slideshow
Show Prices
$104 - $179 Avg. price/night*
Ollie #1 of 2 hotels in Chestertown
Professional photos | Traveler photos (30)
Special Offer Save 10-30%
1008 Rolphs Wharf Road, Chestertown, MD 21620
Ollie #8 of 12 B&Bs / Inns in Chestertown
  •  Heads above the rest! 
  • My husband, mother-in-law, our two dogs and I had a(nother) excellent... more
  • June 27, 2014
160 Scheeler Rd., Chestertown, MD 21620
Comfort Suites Slideshow
Show Prices
$98 - $154 Avg. price/night*
Ollie #2 of 2 hotels in Chestertown
Professional photos | Traveler photos (14)
Special Offer Choice Privileges Points
954 High Street, Chestertown, MD 21620
Ollie #9 of 12 B&Bs / Inns in Chestertown
  •  Faded Glory 
  • Four "tall ships" were going to be in Chestertown, Maryland, for the... more
  • November 23, 2013
Traveler photos (3)
160 Claddaugh Lane, Chestertown, MD 21620
$75 - $95 Avg. price/night*
Ollie #10 of 12 B&Bs / Inns in Chestertown
  •  Nice Stay 
  • Whilst browsing I noted no reviews in last several years so I'll add one... more
  • August 24, 2011
Traveler photos (1)
609 Washington Avenue, Chestertown, MD 21620
Show Prices
$62 - $63 Avg. price/night*
Ollie #11 of 12 B&Bs / Inns in Chestertown
  •  Quaint and memorable 
  • It is right on the beach. With pets and sand, the tile floors make sense... more
  • March 18, 2015
Professional photos | Traveler photos (8)
108 Spring Ave, Chestertown, MD 21620