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Search results; 525 homes in Chesapeake City

Top guest favourite
Room in Chesapeake City
Cafe on the Bay 2- breakfast included!
1 bedroom, 1 bed, 1 shared bathroom
19–24 Jul
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4.92 out of 5 average rating, 309 reviews
Home in Chesapeake City
Floral Canal-Facing Hideaway
New place to stay, 2 bedrooms, 4 beds, 1 bathroom
19–24 Jul
Top guest favourite
Flat in Chesapeake City
The Pearl: A hip & cozy canal-side apartment
4.98 out of 5 average rating, 51 reviews, 2 bedrooms, 4 beds, 1 bathroom
3–8 Aug
Top guest favourite
Home in Chesapeake City
McReynolds-Woods House -Private 3 Bedroom Home
5.0 out of 5 average rating, 61 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
19–24 Jul
Top guest favourite
Cottage in Chesapeake City
Bohemia Bungalow
5.0 out of 5 average rating, 122 reviews, 1 bedroom, 1 bed, 1 bathroom
24–29 Jul
Top guest favourite
Home in Chesapeake City
Modish Cottage - Walk to everything!
5.0 out of 5 average rating, 24 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
19–24 Jul
Guest favourite
Home in Chesapeake City
The Mint Cottage in Chesapeake City
4.9 out of 5 average rating, 113 reviews, 3 bedrooms, 4 beds, 3 bathrooms
26–31 Jul
Top guest favourite
Home in Chesapeake City
The Chandler House
4.98 out of 5 average rating, 61 reviews, 2 bedrooms, 3 beds, 2 bathrooms
19–24 Jul
Top guest favourite
Home in Chesapeake City
Historic Victorian Walkability Chesapeake City
5.0 out of 5 average rating, 12 reviews, 5 bedrooms, 6 beds, 4 bathrooms
10–15 Aug
Guest favourite
Home in Chesapeake City
The Ferry Slip House
4.96 out of 5 average rating, 69 reviews, 2 bedrooms, 2 beds, 2 bathrooms
24–29 Jul
Top guest favourite
Guest suite in Chesapeake City
Benson House on Bohemia Ave (Back Deck)
5.0 out of 5 average rating, 119 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Top guest favourite
Room in Chesapeake City
Benson House on Bohemia Ave. - Front
4.99 out of 5 average rating, 144 reviews, 1 king bed, 1 bathroom
10–15 Aug
Guest favourite
Home in Chesapeake City
Captain’s Cottage Retreat
4.92 out of 5 average rating, 24 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
20–25 Jul
Top guest favourite
Home in Chesapeake City
Chesapeake City Charm at the Boho House!
5.0 out of 5 average rating, 58 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
29 Aug – 3 Sept
Top guest favourite
Flat in Chesapeake City
Hygge Haven: A cozy apartment in a canal-side town
4.94 out of 5 average rating, 124 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Aug
Top guest favourite
Home in Chesapeake City
Canal views/Walk to Shops/Luxury 2Bed/1.5Bath
5.0 out of 5 average rating, 31 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
30 Aug – 4 Sept
Top guest favourite
Home in Chesapeake City
Breathtaking views!
5.0 out of 5 average rating, 23 reviews, 5 bedrooms, 7 beds, 6 bathrooms
17–22 Aug
Guest favourite
Home in Chesapeake City
HOOK WINE & SINKER sleeps 14 w/ Boat Slip and Inn
4.9 out of 5 average rating, 50 reviews, 5 bedrooms, 8 beds, 3 bathrooms
18–23 Jul
Home in Elkton
The C&D Retreat
New place to stay, 3 bedrooms, 4 beds, 2 bathrooms
18–23 Jul