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

 

Traveller rating

 

Hotel class

 

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 (11)

Speciality 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 Travellers Trust

Sort by [ Popularity ] [ Price ]
25227 Chestertown Rd, Chestertown, MD 21620-3944
Show Prices
US$186 - US$288 Avg. price/night*
Ollie #1 of 11 B&Bs / Inns in Chestertown
Professional photos | Traveller photos (174)
Offers & Announcements 🌹 February Special
10568 Cliff Rd, Chestertown, MD 21620-4115
Show Prices
US$165 - US$310 Avg. price/night*
Ollie #2 of 11 B&Bs / Inns in Chestertown
Professional photos | Traveller photos (209)
Special Offer Celebrate the Love Month
208 Mount Vernon Ave, Chestertown, MD 21620-1324
US$99 - US$139 Avg. price/night*
Ollie #3 of 11 B&Bs / Inns in Chestertown
Traveller photos (20)
8796 Maryland Pkwy, Chestertown, MD 21620-4209
Show Prices
US$165 - US$199 Avg. price/night*
Ollie #4 of 11 B&Bs / Inns in Chestertown
  •  Maryland Memory 
  • 9 friends & l went on a waterfowl hunting trip in MD and stayed at the Inn... more
  • 11 February 2018
Traveller photos (37)
231 High St, Chestertown, MD 21620-1517
US$30 - US$180 Avg. price/night*
Ollie #5 of 11 B&Bs / Inns in Chestertown
Traveller photos (63)
402 High St., Chestertown, MD 21620-1312
No photo provided
US$30 - US$135 Avg. price/night*
Ollie #6 of 11 B&Bs / Inns in Chestertown
  •  Charm & Comfort 
  • This was my first experience staying at a bed and breakfast and I have to... more
  • 16 October 2017
114 Washington Ave, Chestertown, MD 21620-1616
Show Prices
US$209 - US$244 Avg. price/night*
Ollie #7 of 11 B&Bs / Inns in Chestertown
  •  Magical Evening 
  • My wife and I stayed at the John L Stam House in Chestertown, MD during... more
  • 5 December 2017
Traveller photos (15)
150 Scheeler Rd, Chestertown, MD 21620-1031
Show Prices
US$94 - US$249 Avg. price/night*
Ollie #1 of 2 hotels in Chestertown
  •  Wedding trip 
  • Stayed here to be near a friends wedding. Hotel was fine. Very clean... more
  • 3 January 2018
Professional photos | Traveller photos (33)
Special Offer Save on Hotel Packages!
208 High St, Chestertown, MD 21620-1518
Ollie #8 of 11 B&Bs / Inns in Chestertown
1008 Rolphs Wharf Rd, Chestertown, MD 21620-2012
Ollie #9 of 11 B&Bs / Inns in Chestertown
  •  Summer memories 
  • This is our second stay at The River Inn. We stayed at another B&B but our... more
  • 23 August 2016
Traveller photos (12)
160 Claddaugh Ln, Chestertown, MD 21620-2311
US$75 - US$95 Avg. price/night*
Ollie #10 of 11 B&Bs / Inns in Chestertown
  •  Nice Stay 
  • Whilst browsing I noted no reviews in last several years so I'll add one... more
  • 24 August 2011
Traveller photos (1)
160 Scheeler Rd., Chestertown, MD 21620-1031
Show Prices
US$87 - US$188 Avg. price/night*
Ollie #2 of 2 hotels in Chestertown
Traveller photos (46)
609 Washington Avenue, Chestertown, MD 21620
Show Prices
US$62 - US$131 Avg. price/night*
Ollie #11 of 11 B&Bs / Inns in Chestertown
  •  Better than expected 
  • I stayed here the night before racing a half Ironman triathlon. My race... more
  • 1 October 2017
Professional photos | Traveller photos (24)