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Search results; 511 homes in Chesapeake City

Top guest favourite
Cottage in Chesapeake City
Bohemia Bungalow
1 bedroom, 1 bed, 1 private bathroom
27 Sept – 2 Oct
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5.0 out of 5 average rating, 131 reviews
Top guest favourite
Room in Chesapeake City
Cafe on the Bay 2- breakfast included!
1 queen bed
14–19 Sept
4.92 out of 5 average rating, 315 reviews
Top guest favourite
Home in Chesapeake City
McReynolds-Woods House -Private 3 Bedroom Home
3 bedrooms, 4 beds
13–18 Sept
5.0 out of 5 average rating, 66 reviews
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Home in Chesapeake City
The Chandler House
2 bedrooms, 3 beds
20–25 Sept
4.98 out of 5 average rating, 66 reviews
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Home in Chesapeake City
Historic Victorian Walkability Chesapeake City
5 bedrooms, 6 beds
10–15 Nov
5.0 out of 5 average rating, 14 reviews
Guest favourite
Home in Chesapeake City
The Mint Cottage in Chesapeake City
3 bedrooms, 4 beds
13–18 Sept
4.9 out of 5 average rating, 118 reviews
Top guest favourite
Flat in Chesapeake City
The Pearl: A hip & cozy canal-side apartment
2 bedrooms, 2 beds
6–11 Sept
4.98 out of 5 average rating, 59 reviews
Top guest favourite
Home in Chesapeake City
The Ferry Slip House
2 bedrooms, 2 beds
13–18 Sept
4.96 out of 5 average rating, 73 reviews
Top guest favourite
Home in Chesapeake City
Chesapeake City Charm at the Boho House!
3 bedrooms, 3 beds
1–6 Dec
5.0 out of 5 average rating, 64 reviews
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Home in Chesapeake City
Breathtaking views!
5 bedrooms, 7 beds
12–17 Oct
5.0 out of 5 average rating, 26 reviews
Guest favourite
Home in Chesapeake City
Floral Canal-Facing Hideaway
2 bedrooms, 4 beds
15–20 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Chesapeake City
Canal views/Walk to Shops/Luxury 2Bed/1.5Bath
2 bedrooms, 2 beds
19–24 Sept
5.0 out of 5 average rating, 31 reviews
Home in Chesapeake City
Cozy Water View Getaway, 3 bds, backyard, deck
3 bedrooms, 4 beds
7–12 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Chesapeake City
Modish Cottage - Walk to everything!
2 bedrooms, 2 queen beds
13–18 Sept
5.0 out of 5 average rating, 29 reviews
Guest favourite
Flat in Chesapeake City
Historic Chesapeake City Stay
1 bedroom, 1 queen bed
13–18 Sept
4.73 out of 5 average rating, 110 reviews
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Flat in Chesapeake City
Hygge Haven: A cozy apartment in a canal-side town
1 bedroom, 1 queen bed
5–10 Oct
4.95 out of 5 average rating, 129 reviews
Top guest favourite
Room in Chesapeake City
Benson House on Bohemia Ave. - Front
1 king bed
14–19 Sept
4.99 out of 5 average rating, 149 reviews
Superhost
Home in Chesapeake City
Chesapeake City MD Staycation
3 bedrooms, 4 beds
21–26 Sept
4.7 out of 5 average rating, 87 reviews
Guest favourite
Home in Chesapeake City
Captain’s Cottage Retreat
3 bedrooms, 4 beds
21–26 Sept
4.93 out of 5 average rating, 27 reviews