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.
$25 Amazon.com Gift Card Get yours when you book a hotel on TripAdvisor and review your stay!

Brampton Bed and Breakfast Inn

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 Brampton Bed and Breakfast Inn

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 ]
25227 Chestertown Rd, Chestertown, MD 21620-3944
Brampton Bed and Breakfast Inn Slideshow
Show Prices
$237 - $316 Avg. price/night*
Ollie #1 of 12 B&Bs / Inns in Chestertown
Professional photos | Traveler photos (126)
Offers & Announcements Fall Retreat & Refresh
Great Oak Manor (Chestertown, MD) 3.5 of 5
10568 Cliff Rd, Chestertown, MD 21620-4115
Great Oak Manor Slideshow
Show Prices
$175 - $297 Avg. price/night*
Ollie #2 of 12 B&Bs / Inns in Chestertown
Professional photos | Traveler photos (158)
Special Offer Buy One Get One FREE
Simply Bed and Bread (Chestertown, MD)
208 Mount Vernon Ave, Chestertown, MD 21620-1324
$99 - $139 Avg. price/night*
Ollie #3 of 12 B&Bs / Inns in Chestertown
Traveler photos (19)
150 Scheeler Rd, Chestertown, MD 21620-1031
Holiday Inn Express Hotel & Suites Chestertown Slideshow
Show Prices
$100 - $201 Avg. price/night*
Ollie #1 of 2 hotels in Chestertown
Professional photos | Traveler photos (29)
Special Offer Book Direct and Save
The Inn at Mitchell House (Chestertown, MD)
8796 Maryland Pkwy, Chestertown, MD 21620-4209
The Inn at Mitchell House Slideshow
$109 - $239 Avg. price/night*
Ollie #4 of 12 B&Bs / Inns in Chestertown
Traveler photos (30)
Widow's Walk Inn (Chestertown, MD)
402 High St, Chestertown, MD 21620-1312
No photo provided
$30 - $135 Avg. price/night*
Ollie #5 of 12 B&Bs / Inns in Chestertown
John Stam House (Chestertown, MD) 3.0 of 5
114 Washington Ave, Chestertown, MD 21620-1616
Show Prices
$193 - $244 Avg. price/night*
Ollie #6 of 12 B&Bs / Inns in Chestertown
Professional photos | Traveler photos (13)
The River Inn (Chestertown, MD)
1008 Rolphs Wharf Rd, Chestertown, MD 21620-2012
Ollie #7 of 12 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)
White Swan Tavern (Chestertown, MD)
231 High St, Chestertown, MD 21620-1517
$30 - $180 Avg. price/night*
Ollie #8 of 12 B&Bs / Inns in Chestertown
  •  Disappointing at best 
  • Disappointing. Expensive. Worst breakfast in our B&B experience. They... more
  • September 12, 2016
Traveler photos (2)
The Imperial (Chestertown, MD)
208 High St, Chestertown, MD 21620-1518
Ollie #9 of 12 B&Bs / Inns in Chestertown
160 Claddaugh Ln, Chestertown, MD 21620-2311
$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)
Quality Suites (Chestertown, MD) 2.5 of 5
160 Scheeler Rd, Chestertown, MD 21620
Quality Suites Slideshow
Show Prices
$91 - $189 Avg. price/night*
Ollie #2 of 2 hotels in Chestertown
  •  Parents Weekend Visit 
  • We arrived prior to noon at the hotel and asked for a first floor room... more
  • September 23, 2016
Professional photos | Traveler photos (28)
Special Offer Choice Privileges Points
954 High St, Chestertown, MD 21620-3955
Ollie #11 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)
Driftwood Inn (Chestertown, MD) 2.0 of 5
609 Washington Ave, Chestertown, MD 21620-1219
Show Prices
$62 - $91 Avg. price/night*
Ollie #12 of 12 B&Bs / Inns in Chestertown
  •  Unkept 
  • I should have known, when we saw no cars in the parking lot. It looked... more
  • August 9, 2016
Professional photos | Traveler photos (8)

Additional Brampton Bed and Breakfast Inn Information

5.0 of 5 stars | 563 Reviews
Price range (per night): $62 - $91