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Map of Chestertown Hotels

Hotels (3)

B&Bs / Inns (12)

Specialty Lodging (0)

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Chestertown weather essentials

Month
High
Low
May
68°F 20°C
54°F 12°C
Jun
76°F 24°C
63°F 17°C
Jul
80°F 26°C
68°F 20°C
Aug
79°F 26°C
68°F 20°C
Sep
71°F 21°C
59°F 15°C
Oct
60°F 15°C
49°F 9°C
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Hotels Travelers Trust

Sort by [ Popularity ] [ Price ]
Simply Bed and Bread
208 Mount Vernon Ave, Chestertown, MD
Simply Bed and Bread
$99 - $139 Avg. price/night*
5 of 5 stars 101 reviews
Ollie #1 of 12 B&Bs / Inns in Chestertown
Traveler photos (12)
Brampton Bed and Breakfast Inn
25227 Chestertown Road, Chestertown, MD 21620
Brampton Bed and Breakfast Inn Slideshow
$169 - $399 Avg. price/night*
5 of 5 stars 273 reviews
Ollie #2 of 12 B&Bs / Inns in Chestertown
  • “ Great getaway weekend ”
  • We stayed 3 day in the Russell cottage in May. The grounds were amazing... more
  • May 13, 2013
Traveler photos (78)
Offers & Announcements
20% off Spring Special
The Inn at Mitchell House
8796 Maryland Pkwy., Chestertown, MD 21620
The Inn at Mitchell House Slideshow
$109 - $239 Avg. price/night*
5 of 5 stars 42 reviews
Ollie #3 of 12 B&Bs / Inns in Chestertown
Traveler photos (22)
Announcement
27 Six Years!
Great Oak Manor Inn
10568 Cliff Rd, Chestertown, MD 21620
Great Oak Manor Inn
$165 - $310 Avg. price/night*
5 of 5 stars 131 reviews
Ollie #4 of 12 B&Bs / Inns in Chestertown
Traveler photos (52)
White Swan Tavern
231 High St, Chestertown, MD 21620
White Swan Tavern
$30 - $180 Avg. price/night*
4.5 of 5 stars 18 reviews
Ollie #5 of 12 B&Bs / Inns in Chestertown
Traveler photos (2)
Holiday Inn Express Hotel & Suites Chestertown 2.5 of 5
150 Scheeler Road, Chestertown, MD 21620
Holiday Inn Express Hotel & Suites Chestertown Slideshow
Show Prices ABS:HotelCheckRates-d672957?&src=LocalMapsRedesign&fromServlet=LocalMapsRedesign&Action=QC_Button
$111 - $211 Avg. price/night*
4 of 5 stars 52 reviews
Ollie #1 of 3 hotels in Chestertown
Professional photos | Traveler photos (26)
Special Offer
Save on Hotel Packages!
John Stam House
114 Washington Ave, Chestertown, MD
John Stam House
5 of 5 stars 3 reviews
Ollie #6 of 12 B&Bs / Inns in Chestertown
  • “ Great B&B ”
  • We had a very enjoyable stay. The Inn is meticuously decorated. It was... more
  • October 8, 2012
Traveler photos (1)
Widow's Walk Inn
402 High St., Chestertown, MD 21620
Widow's Walk Inn
$30 - $135 Avg. price/night*
4.5 of 5 stars 13 reviews
Ollie #7 of 12 B&Bs / Inns in Chestertown
  • “ Bob is great, ”
  • There are a lot of us out there that need to take deep breath when writing... more
  • February 4, 2013
Traveler photos (3)
Comfort Suites 2.5 of 5
160 Scheeler Rd., Chestertown, MD 21620
Comfort Suites Slideshow
Show Prices ABS:HotelCheckRates-d93725?&src=LocalMapsRedesign&fromServlet=LocalMapsRedesign&Action=QC_Button
$121 - $165 Avg. price/night*
4 of 5 stars 72 reviews
Ollie #2 of 3 hotels in Chestertown
  • “ Weekend Stay ”
  • Hotel staff was very nice, free breakfast was ok, a lot of screaming kids... more
  • April 7, 2013
Professional photos | Traveler photos (11)
Special Price
Book Early-Save up to...
The Imperial Hotel and Restaurant
208 High Street, Chestertown, MD 21620
The Imperial Hotel and Restaurant
$95 - $250 Avg. price/night*
3.5 of 5 stars 29 reviews
Ollie #3 of 3 hotels in Chestertown
  • “ A favorite spot ”
  • Lovely rooms, excellent food. The place has a great atmosphere and... more
  • February 25, 2013
Traveler photos (15)
The River Inn
1008 Rolphs Wharf Road, Chestertown, MD 21620
No photo provided
4.5 of 5 stars 2 reviews
Ollie #8 of 12 B&Bs / Inns in Chestertown
Lauretum Inn Bed and Breakfast
954 High Street, Chestertown, MD 21620
Lauretum Inn Bed and Breakfast
4 of 5 stars 5 reviews
Ollie #9 of 12 B&Bs / Inns in Chestertown
Traveler photos (3)
Claddaugh Farm Bed and Breakfast
160 Claddaugh Lane, Chestertown, MD 21620
Claddaugh Farm Bed and Breakfast
$75 - $95 Avg. price/night*
4.5 of 5 stars 3 reviews
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 (2)
Driftwood Inn
609 Washington Avenue, Chestertown, MD 21620
Driftwood Inn
Show Prices ABS:HotelCheckRates-d483921?&src=LocalMapsRedesign&fromServlet=LocalMapsRedesign&Action=QC_Button
$63 - $96 Avg. price/night*
2.5 of 5 stars 13 reviews
Ollie #11 of 12 B&Bs / Inns in Chestertown
  • “ Do not stay here ”
  • This place is a dump. We reserved two rooms with two queen beds. They only... more
  • May 20, 2013
Professional photos | Traveler photos (8)
The Parker House
108 Spring Ave, Chestertown, MD 21620
No photo provided