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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$218 - US$286 Avg. price/night*
Ollie #1 of 11 B&Bs in Chestertown
Traveller photos (187)
Special Offer 🎄This Holiday save $40
208 Mount Vernon Ave, Chestertown, MD 21620-1324
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US$99 - US$139 Avg. price/night*
Ollie #2 of 11 B&Bs in Chestertown
  •  Simply...Delightful! 
  • What a lovely b&b in Chestertown! Our hosts were friendly, thoughtful, and... more
  • 22 September 2018
Traveller photos (20)
10568 Cliff Rd, Chestertown, MD 21620-4115
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US$175 - US$249 Avg. price/night*
Ollie #3 of 11 B&Bs in Chestertown
  •  Much needed R&R 
  • The Great Oak Manor is a beautiful estate. The landscape is beautiful... more
  • 29 October 2018
Traveller photos (252)
Offers & Announcements 🎉Midweek Special✨
8796 Maryland Pkwy, Chestertown, MD 21620-4209
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US$165 - US$182 Avg. price/night*
Ollie #4 of 11 B&Bs in Chestertown
Traveller photos (54)
Special Rate 1/2 off second night
402 High St, Chestertown, MD 21620-1312
No photo provided
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US$30 - US$135 Avg. price/night*
Ollie #5 of 11 B&Bs in Chestertown
150 Scheeler Rd, Chestertown, MD 21620-1031
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US$92 - US$190 Avg. price/night*
Ollie #1 of 2 hotels in Chestertown
Traveller photos (35)
Special Offer Annual Sale
231 High St, Chestertown, MD 21620-1517
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US$30 - US$180 Avg. price/night*
Ollie #6 of 11 B&Bs in Chestertown
  •  Charming, historic inn 
  • This is truly an old fashioned inn. If you measure your expectations from... more
  • 9 October 2018
Traveller photos (65)
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
  •  Fantastic Inn 
  • John L Stam House is beautifully decorated, wonderfully comfortable, and... more
  • 25 September 2018
Traveller photos (15)
160 Scheeler Rd, Chestertown, MD 21620-1031
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US$93 - US$161 Avg. price/night*
Ollie #2 of 2 hotels in Chestertown
Traveller photos (37)
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
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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$65 - US$150 Avg. price/night*
Ollie #11 of 11 B&Bs in Chestertown
  •  Stay Away 
  • I stay in motels and hotels all over the world. I’ve stayed in many places... more
  • 29 October 2018
Traveller photos (29)