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Chestertown

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Map of Chestertown Hotels

Hotels (2)

B&Bs / Inns (11)

Specialty Lodging (0)

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25227 Chestertown Rd, Chestertown, MD 21620-3944
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$214 - $381 Avg. price/night*
Ollie #1 of 11 B&Bs / Inns in Chestertown
Professional photos | Traveler photos (177)
Offers & Announcements 🍷 Spring Winery Special
208 Mount Vernon Ave, Chestertown, MD 21620-1324
$99 - $139 Avg. price/night*
Ollie #2 of 11 B&Bs / Inns in Chestertown
Traveler photos (20)
10568 Cliff Rd, Chestertown, MD 21620-4115
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$182 - $302 Avg. price/night*
Ollie #3 of 11 B&Bs / Inns in Chestertown
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Offers & Announcements Luxury Romance Package...
8796 Maryland Pkwy, Chestertown, MD 21620-4209
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$165 - $182 Avg. price/night*
Ollie #4 of 11 B&Bs / Inns in Chestertown
Traveler photos (53)
150 Scheeler Rd, Chestertown, MD 21620-1031
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$113 - $247 Avg. price/night*
Ollie #1 of 2 hotels in Chestertown
Professional photos | Traveler photos (33)
Special Offer Book Direct and Save
231 High St, Chestertown, MD 21620-1517
$30 - $180 Avg. price/night*
Ollie #5 of 11 B&Bs / Inns in Chestertown
Traveler photos (65)
402 High St, Chestertown, MD 21620-1312
No photo provided
$30 - $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
  • October 16, 2017
114 Washington Ave, Chestertown, MD 21620-1616
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$209 - $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
  • December 5, 2017
Traveler photos (15)
160 Scheeler Rd, Chestertown, MD 21620-1031
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$94 - $227 Avg. price/night*
Ollie #2 of 2 hotels in Chestertown
  •  Never stay here again 
  • This place is really old and in bad shape. For nearly $200 per night, this... more
  • June 3, 2018
Traveler photos (46)
1008 Rolphs Wharf Rd, Chestertown, MD 21620-2012
Ollie #8 of 11 B&Bs / Inns in Chestertown
Traveler photos (17)
208 High St, Chestertown, MD 21620-1518
Ollie #9 of 11 B&Bs / Inns in Chestertown
160 Claddaugh Ln, Chestertown, MD 21620-2311
$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 Ave, Chestertown, MD 21620-1219
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$70 - $150 Avg. price/night*
Ollie #11 of 11 B&Bs / Inns in Chestertown
  •  Bad experience 
  • Came home with a case of bed bugs. Did not feel safe sleeping at night as... more
  • May 15, 2018
Professional photos | Traveler photos (24)