Chestertown Bed and Breakfasts

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from $175

Rock Hall, MD (11 miles from Chestertown)

4.6 (131)
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from $159

Chestertown, MD (22 miles from Chestertown)

4.5 (96)
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from $199

Chestertown, MD (28 miles from Chestertown)

4.9 (40)
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from $189

Annapolis, MD (27 miles from Chestertown)

4.8 (146)
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from $170

Annapolis, MD (27 miles from Chestertown)

4.9 (7)

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from $129

Annapolis, MD (27 miles from Chestertown)

4.2 (32)
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from $110

Baltimore, MD (30 miles from Chestertown)

4.5 (57)
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from $105

Rock Hall, MD (10 miles from Chestertown)

4.6 (124)

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from $125

Rock Hall, MD (11 miles from Chestertown)

4.5 (135)
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from $149

Havre De Grace, MD (23 miles from Chestertown)

4.7 (50)
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from $90

Chesapeake City, MD (25 miles from Chestertown)

4.5 (189)
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from $259

Annapolis, MD (27 miles from Chestertown)

4.6 (1)
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from $140

Baltimore, MD (27 miles from Chestertown)

4.7 (265)
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from $250

Easton, MD (28 miles from Chestertown)

4.6 (46)

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from $125

Dover, DE (29 miles from Chestertown)

4.9 (2)
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from $199

Baltimore, MD (29 miles from Chestertown)

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from $140

Chestertown, MD (21 miles from Chestertown)

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Cordova, MD (21 miles from Chestertown)

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from $110

Chesapeake City, MD (25 miles from Chestertown)

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Odessa, DE (27 miles from Chestertown)

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Annapolis, MD (27 miles from Chestertown)

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from $174

Baltimore, MD (28 miles from Chestertown)

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from $243

Easton, MD (28 miles from Chestertown)

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from $249

Baltimore, MD (29 miles from Chestertown)

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from $93

Baltimore, MD (29 miles from Chestertown)

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from $130

St Michaels, MD (29 miles from Chestertown)

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from $70

Baltimore, MD (30 miles from Chestertown)

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from $189

Baltimore, MD (30 miles from Chestertown)

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from $160

Easton, MD (30 miles from Chestertown)

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from $289

Easton, MD (30 miles from Chestertown)

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from $189

Easton, MD (30 miles from Chestertown)

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from $190

Chestertown, MD (30 miles from Chestertown)

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St Michaels, MD (30 miles from Chestertown)

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St Michaels, MD (30 miles from Chestertown)

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Chestertown B&B reviews

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The Chestertown B&B review score is based on feedback from travelers from around the world. See property page for full, detailed reviews by real travelers.

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