Best price vacation rentals in Chesapeake City, MD, USA • 29 Listings
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Chesapeake City, MD, USA Vacation Rentals | 

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5.0 (91)
Summer Season in Chesapeake City, MD Old Lock View @ C&D Canal
Up to 8 guests
Airbnb$386
Vrbo$386
Average Nightly Rate
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5.0 (77)
Waterfront Retreat for Weekends and More!
Up to 8 guests
Airbnb$349
Vrbo$349
Average Nightly Rate
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5.0 (42)
Short Term Water Oriented Furnished Apartment
Up to 2 guests
Airbnb$141
Vrbo$141
Average Nightly Rate
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5.0 (45)
Chesapeake City MD Staycation
Up to 6 guests
Airbnb$300
Average Nightly Rate
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5.0 (144)
Cafe on the Bay 2- breakfast included!
Up to 2 guests
Airbnb$118
Average Nightly Rate
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5.0 (92)
High-End Cottage, Water View, Chesapeake City, MD
Up to 2 guests
Airbnb$181
Average Nightly Rate
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5.0 (64)
Tranquility
Up to 2 guests
Airbnb$134
Average Nightly Rate

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5.0 (75)
Cafe on the Bay - breakfast included!
Up to 2 guests
Airbnb$118
Average Nightly Rate
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5.0 (42)
Benson House on Bohemia Ave. - Front
Up to 2 guests
Airbnb$150
Average Nightly Rate

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5.0 (33)
Benson House on Bohemia Ave (Back Deck)
Up to 2 guests
Airbnb$175
Average Nightly Rate
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5.0 (8)
Relaxing Country Elegance on Waterfront Property
Up to 2 guests
Airbnb$299
Average Nightly Rate
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5.0 (50)
Chesapeake Charm in Historic Chesapeake City, MD
Up to 4 guests
Airbnb$146
Average Nightly Rate
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5.0 (50)
The Checkered Rabbit
Up to 4 guests
Airbnb$218
Average Nightly Rate
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5.0 (13)
Chesapeake City Charm at the Boho House!
Up to 6 guests
Airbnb$700
Average Nightly Rate
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5.0 (19)
The Mint Cottage in Chesapeake City
Up to 6 guests
Airbnb$435
Average Nightly Rate
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5.0 (6)
Henny’s Place
Up to 4 guests
Airbnb$280
Average Nightly Rate
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5.0 (1)
Hook Wine & Sinker
Up to 14 guests
Vrbo$916
Average Nightly Rate
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The Checkered Rabbit
Up to 4 guests
Vrbo$237
Average Nightly Rate
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HOOK WINE & SINKER sleeps 14
Up to 14 guests
Airbnb$786
Average Nightly Rate
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Ship Watch Inn - Waterfront - Caroline Room
Up to 2 guests
Airbnb$211
Average Nightly Rate
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Ship Watch Inn - Waterfront - Dorchester Room
Up to 2 guests
Airbnb$211
Average Nightly Rate
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Ship Watch Inn - Waterfront - Kent Room
Up to 2 guests
Airbnb$186
Average Nightly Rate
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Ship Watch Inn - Waterfront - Wicomico Room
Up to 2 guests
Airbnb$213
Average Nightly Rate
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Ship Watch Inn - Waterfront - Annapolis Suite
Up to 2 guests
Airbnb$257
Average Nightly Rate
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Ship Watch Inn - Waterfront - Queen Anne
Up to 2 guests
Airbnb$213
Average Nightly Rate
  1. United States
  2. Maryland
  3. Chesapeake City Vacation Rental Price Comparison

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