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.
Want the lowest hotel prices? You're in the right place. We check 200+ sites for you.

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 (11)

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 ]
25227 Chestertown Rd., Chestertown, MD 21620
Brampton Bed and Breakfast Inn Slideshow
Show Prices
$238 - $320 Avg. price/night*
Ollie #1 of 11 B&Bs / Inns in Chestertown
Professional photos | Traveler photos (145)
Offers & Announcements Spring Break Special
10568 Cliff Rd, Chestertown, MD 21620
Show Prices
$143 - $280 Avg. price/night*
Ollie #2 of 11 B&Bs / Inns in Chestertown
Professional photos | Traveler photos (166)
208 Mount Vernon Ave, Chestertown, MD 21620-1324
$99 - $139 Avg. price/night*
Ollie #3 of 11 B&Bs / Inns in Chestertown
Traveler photos (20)
150 Scheeler Rd, Chestertown, MD 21620-1031
Holiday Inn Express Hotel & Suites Chestertown Slideshow
Show Prices
$99 - $172 Avg. price/night*
Ollie #1 of 2 hotels in Chestertown
Professional photos | Traveler photos (29)
Special Offer Book Direct and Save
8796 Maryland Pkwy., Chestertown, MD 21620
Show Prices
$165 - $166 Avg. price/night*
Ollie #4 of 11 B&Bs / Inns in Chestertown
Professional photos | Traveler photos (31)
402 High St., Chestertown, MD 21620
No photo provided
$30 - $135 Avg. price/night*
Ollie #5 of 11 B&Bs / Inns in Chestertown
114 Washington Ave, Chestertown, MD 21620-1616
Show Prices
$193 - $244 Avg. price/night*
Ollie #6 of 11 B&Bs / Inns in Chestertown
Professional photos | Traveler photos (13)
231 High St, Chestertown, MD 21620
$30 - $180 Avg. price/night*
Ollie #7 of 11 B&Bs / Inns in Chestertown
Traveler photos (50)
1008 Rolphs Wharf Rd, Chestertown, MD 21620-2012
Ollie #8 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
  • August 23, 2016
Traveler photos (12)
208 High St, Chestertown, MD 21620-1518
Ollie #9 of 11 B&Bs / Inns in Chestertown
160 Scheeler Rd., Chestertown, MD 21620
Quality Suites Slideshow
Show Prices
$69 - $138 Avg. price/night*
Ollie #2 of 2 hotels in Chestertown
Professional photos | Traveler photos (44)
Special Offer Choice Privileges Points
160 Claddaugh Lane, Chestertown, MD 21620
$75 - $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
  • August 24, 2011
Traveler photos (1)
609 Washington Avenue, Chestertown, MD 21620
No photo provided
Show Prices
$62 - $87 Avg. price/night*
Ollie #11 of 11 B&Bs / Inns in Chestertown
  •  would stay clear 
  • This is not a great place to stay - and not a good value. I would advise... more
  • January 24, 2017
Professional photos | Traveler photos (8)