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Chestertown

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Map of Chestertown Hotels

Hotels (2)

B&Bs / Inns (11)

Speciality Lodging (0)

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Hotels Travellers Trust

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25227 Chestertown Rd, Chestertown, MD 21620-3944
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US$167 - US$326 Avg. price/night*
Ollie #1 of 11 B&Bs in Chestertown
Professional photos | Traveller photos (177)
Offers & Announcements Summer Escape 30% off
208 Mount Vernon Ave, Chestertown, MD 21620-1324
US$99 - US$139 Avg. price/night*
Ollie #2 of 11 B&Bs in Chestertown
Traveller photos (20)
10568 Cliff Rd, Chestertown, MD 21620-4115
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US$174 - US$395 Avg. price/night*
Ollie #3 of 11 B&Bs in Chestertown
  •  Fantastic! 
  • This is the place to relax! Holly, Richard and Cass are truly welcoming... more
  • 21 July 2018
Professional photos | Traveller photos (242)
Offers & Announcements ☀️Summer Midweek Special
8796 Maryland Pkwy, Chestertown, MD 21620-4209
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US$165 - US$221 Avg. price/night*
Ollie #4 of 11 B&Bs in Chestertown
  •  Peace and Plenty 
  • This is a property that truly lets the traveler get away from the noise... more
  • 5 July 2018
Traveller photos (54)
150 Scheeler Rd, Chestertown, MD 21620-1031
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US$105 - US$227 Avg. price/night*
Ollie #1 of 2 hotels in Chestertown
  •  Needs cleaning 
  • The rooms were adequately appointed and overall ok. My big complaint at... more
  • 15 July 2018
Professional photos | Traveller photos (34)
Special Offer Book Direct and Save
231 High St, Chestertown, MD 21620-1517
US$30 - US$180 Avg. price/night*
Ollie #5 of 11 B&Bs in Chestertown
Traveller photos (65)
402 High St, Chestertown, MD 21620-1312
No photo provided
US$30 - US$135 Avg. price/night*
Ollie #6 of 11 B&Bs 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
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US$209 - US$244 Avg. price/night*
Ollie #7 of 11 B&Bs 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)
160 Scheeler Rd, Chestertown, MD 21620-1031
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US$88 - US$221 Avg. price/night*
Ollie #2 of 2 hotels in Chestertown
  •  Nice Enough 
  • Was a clean hotel. Friendly staff. Free breakfast was good. Hotel need... more
  • 10 July 2018
Traveller photos (77)
1008 Rolphs Wharf Rd, Chestertown, MD 21620-2012
Ollie #8 of 11 B&Bs in Chestertown
Traveller photos (17)
208 High St, Chestertown, MD 21620-1518
Ollie #9 of 11 B&Bs in Chestertown
160 Claddaugh Ln, Chestertown, MD 21620-2311
US$75 - US$95 Avg. price/night*
Ollie #10 of 11 B&Bs 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)
609 Washington Ave, Chestertown, MD 21620-1219
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US$73 - US$147 Avg. price/night*
Ollie #11 of 11 B&Bs in Chestertown
  •  Bad experience 
  • Came home with a case of bed bugs. Did not feel safe sleeping at night as... more
  • 15 May 2018
Professional photos | Traveller photos (24)