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Search results; 525 homes in Chesapeake City

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Top guest favourite
Cottage in Chesapeake City
Bohemia Bungalow
1 bedroom, 1 bed, 1 private bathroom
14–19 Sept
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5.0 out of 5 average rating, 131 reviews
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Superhost
Room in Chesapeake City
Cafe on the Bay - breakfast included!
1 queen bed, 1 bathroom
15–20 Sept
4.95 out of 5 average rating, 214 reviews
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Top guest favourite
Home in Chesapeake City
McReynolds-Woods House -Private 3 Bedroom Home
3 bedrooms, 4 beds, 1.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 66 reviews
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Superhost
Home in Chesapeake City
Historic Victorian Walkability Chesapeake City
5 bedrooms, 6 beds, 4 bathrooms
7–12 Sept
5.0 out of 5 average rating, 14 reviews
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Superhost
Home in Chesapeake City
The Mint Cottage in Chesapeake City
3 bedrooms, 4 beds, 3 bathrooms
13–18 Sept
4.9 out of 5 average rating, 118 reviews
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Top guest favourite
Home in Chesapeake City
The Chandler House
2 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
4.98 out of 5 average rating, 65 reviews
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Superhost
Home in Chesapeake City
The Ferry Slip House
2 bedrooms, 2 beds, 2 bathrooms
13–18 Sept
4.96 out of 5 average rating, 73 reviews
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Superhost
Flat in Chesapeake City
The Pearl: A hip & cozy canal-side apartment
2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
4.98 out of 5 average rating, 58 reviews
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Top guest favourite
Home in Chesapeake City
Chesapeake City Charm at the Boho House!
3 bedrooms, 3 beds, 2.5 bathrooms
1–6 Dec
5.0 out of 5 average rating, 64 reviews
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Top guest favourite
Home in Chesapeake City
Canal views/Walk to Shops/Luxury 2Bed/1.5Bath
2 bedrooms, 2 beds, 1.5 bathrooms
19–24 Sept
5.0 out of 5 average rating, 31 reviews
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Top guest favourite
Home in Chesapeake City
Breathtaking views!
5 bedrooms, 7 beds, 6 bathrooms
9–14 Nov
5.0 out of 5 average rating, 26 reviews
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Guest favourite
Home in Chesapeake City
Floral Canal-Facing Hideaway
2 bedrooms, 4 beds, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 5 reviews
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Guest favourite
Flat in Chesapeake City
Historic Chesapeake City Stay
1 bedroom, 1 queen bed, 1 bathroom
6–11 Sept
4.74 out of 5 average rating, 108 reviews
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Top guest favourite
Home in Chesapeake City
Modish Cottage - Walk to everything!
2 bedrooms, 2 queen beds, 1.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 29 reviews
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Home in Chesapeake City
Cozy Water View Getaway, 3 bds, backyard, deck
3 bedrooms, 4 beds, 1.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Room in Chesapeake City
Benson House on Bohemia Ave. - Front
1 king bed, 1 bathroom
14–19 Sept
4.99 out of 5 average rating, 149 reviews
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Superhost
Home in Chesapeake City
Chesapeake City MD Staycation
3 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
4.7 out of 5 average rating, 87 reviews
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Superhost
Flat in Chesapeake City
Hygge Haven: A cozy apartment in a canal-side town
1 bedroom, 1 queen bed, 1 bathroom
5–10 Oct
4.95 out of 5 average rating, 128 reviews
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Guest favourite
Home in Chesapeake City
Captain’s Cottage Retreat
3 bedrooms, 4 beds, 1.5 bathrooms
7–12 Sept
4.93 out of 5 average rating, 27 reviews