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Search results; 469 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, 133 reviews
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Room in Chesapeake City
Cafe on the Bay 2- breakfast included!
1 queen bed, 1 bathroom
20–25 Sept
4.92 out of 5 average rating, 316 reviews
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Flat in Chesapeake City
The Pearl: A hip & cozy canal-side apartment
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 61 reviews
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Home in Chesapeake City
McReynolds-Woods House -Private 3 Bedroom Home
3 bedrooms, 4 beds, 1.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 67 reviews
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Home in Chesapeake City
Historic Victorian Walkability Chesapeake City
5 bedrooms, 6 beds, 4 bathrooms
2–7 Jan
5.0 out of 5 average rating, 15 reviews
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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, 65 reviews
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Home in Chesapeake City
The Chandler House
2 bedrooms, 3 beds, 2 bathrooms
20–25 Sept
4.98 out of 5 average rating, 66 reviews
Guest favourite
Home in Chesapeake City
The Mint Cottage in Chesapeake City
3 bedrooms, 4 beds, 3 bathrooms
11–16 Oct
4.9 out of 5 average rating, 118 reviews
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Home in Chesapeake City
The Ferry Slip House
2 bedrooms, 2 beds, 2 bathrooms
11–16 Oct
4.96 out of 5 average rating, 73 reviews
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Home in Chesapeake City
Breathtaking views!
5 bedrooms, 7 beds, 6 bathrooms
12–17 Oct
5.0 out of 5 average rating, 26 reviews
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Flat in Chesapeake City
Hygge Haven: A cozy apartment in a canal-side town
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.95 out of 5 average rating, 129 reviews
Superhost
Home in Chesapeake City
Chesapeake Ship Watch Retreat
3 bedrooms, 3 queen beds, 2.5 bathrooms
16–21 Sept
New place to stay
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Home in Chesapeake City
Floral Canal-Facing Hideaway
2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 6 reviews
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
Top guest favourite
Home in Chesapeake City
Modish Cottage - Walk to everything!
2 bedrooms, 2 queen beds, 1.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 30 reviews
Guest favourite
Home in Chesapeake City
Cozy Water View Getaway, 3 bds, backyard, deck
3 bedrooms, 4 beds, 1.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 5 reviews
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Flat in Chesapeake City
Historic Chesapeake City Stay
1 bedroom, 1 queen bed, 1 bathroom
27 Sept – 2 Oct
4.73 out of 5 average rating, 111 reviews
Guest favourite
Home in Chesapeake City
HOOK WINE & SINKER sleeps 14 w/ Boat Slip and Inn
5 bedrooms, 8 beds, 3 bathrooms
14–19 Sept
4.9 out of 5 average rating, 52 reviews
Superhost
Home in Chesapeake City
Chesapeake City MD Staycation
3 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
4.69 out of 5 average rating, 88 reviews