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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$212 - US$359 Avg. price/night*
Ollie #1 of 11 B&Bs / Inns in Chestertown
  •  Always Good 
  • Met family to go sailIng in Rock Hall. This is our fifth stay at The... more
  • 16 September 2018
Traveller photos (186)
Offers & Announcements 🍁Fall Special, Save $90
208 Mount Vernon Ave, Chestertown, MD 21620-1324
US$99 - US$139 Avg. price/night*
Ollie #2 of 11 B&Bs / Inns 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$186 - US$332 Avg. price/night*
Ollie #3 of 11 B&Bs / Inns in Chestertown
  •  Fabulous Stay 
  • We were in the area for a family wedding, so we didn’t have as much time... more
  • 24 September 2018
Traveller photos (245)
Offers & Announcements 🍂Fall Midweek Special
8796 Maryland Pkwy, Chestertown, MD 21620-4209
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US$165 - US$232 Avg. price/night*
Ollie #4 of 11 B&Bs / Inns in Chestertown
Traveller photos (54)
150 Scheeler Rd, Chestertown, MD 21620-1031
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US$102 - US$295 Avg. price/night*
Ollie #1 of 2 hotels in Chestertown
  •  Great hotel! 
  • Check in process was slow as there was a new staff member on 2nd shift but... more
  • 24 September 2018
Traveller photos (35)
Special Offer Book Direct and Save
402 High St, Chestertown, MD 21620-1312
No photo provided
US$30 - US$135 Avg. price/night*
Ollie #5 of 11 B&Bs / Inns in Chestertown
231 High St, Chestertown, MD 21620-1517
US$30 - US$180 Avg. price/night*
Ollie #6 of 11 B&Bs / Inns in Chestertown
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 / Inns 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$92 - US$237 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 / Inns in Chestertown
Traveller 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
US$75 - US$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
  • 24 August 2011
Traveller photos (1)
609 Washington Ave, Chestertown, MD 21620-1219
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US$73 - US$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
  • 15 May 2018
Traveller photos (29)