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Compare 7 B&B in Chestertown with updated reviews, rates, and availability.
Vandiver Inn
Vandiver Inn
9.4 out of 10, Exceptional, (437)
The price is AED 621
AED 689 total
includes taxes & fees
27 Jun - 28 Jun
Naomi Bed & Breakfast
Naomi Bed & Breakfast
10.0 out of 10, Exceptional, (5)
The price is AED 327
AED 590 total
includes taxes & fees
10 Jul - 11 Jul
Flag House Inn
Flag House Inn
9.8 out of 10, Exceptional, (51)
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Inn at Huntingfield Creek
Inn at Huntingfield Creek
10.0 out of 10, Exceptional, (44)
The price is AED 843
AED 936 total
includes taxes & fees
27 Jun - 28 Jun
Private room for one person 18+ years only. Text for availability 973-477-4574
Private room for one person 18+ years only. Text for availability 973-477-4574
The Annapolis Inn
The Annapolis Inn
9.0 out of 10, Wonderful, (4)
Surf Condominiums - Downtown Bethany
Surf Condominiums - Downtown Bethany
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Other property types in Chestertown
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, (53)
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
9.8 out of 10, Exceptional, (6)
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (36)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Frequently asked questions
Recent reviews of Chestertown hotelsExpedia verified reviews
![Historic Inns of Annapolis](http://images.trvl-media.com/lodging/1000000/50000/42100/42068/5c9aedf4_y.jpg)
Historic Inns of Annapolis
5/5 Excellent
"I can’t say enough good things about this Inn. Location, staff, cleanliness, and amenities were all of a 5 star, first class Inn at Expedia prices. Highly recommend!"
A verified traveler from Reston stayed at Historic Inns of Annapolis
Posted 2 days ago
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