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Vacation rentals in Chesapeake City

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Top-rated vacation rentals in Chesapeake City

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Private room in Chesapeake City
Cafe on the Bay - breakfast included!
We are in the heart of Chesapeake City on the C&D canal within walking distance of all the shops and restaurants. You will enjoy staying above the coffee shop so it’s best suited for early risers if you’re a light sleeer! We are a block away from the 3 wedding venues in town. The 2 bedrooms above the cafe are booked separately with a full bathroom in the hallway for guests to share. This is a great location for 2 couples or a family to book both rooms as it’s a shared bathroom for the 2 rooms.
$118 per night
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Rental unit in Chesapeake City
cozy garden: hygge= happy + cozy
Chesapeake City is a historic town located on the C & D Canal; it's very friendly & it's not unusual to be greeted by locals as you wander around town. The apartment is a bedroom with sitting area, full kitchen and bath. It's in the heart of the town & walkable to all the boutiques, restaurants & nightlife! It comes equipped with a french press, sparkling water, wifi & tv if you just want to chill. It's steps from the canal for lovely sunrise/sunsets! There are bike/walking paths nearby.
$149 per night
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Cottage in Chesapeake City
Bohemia Bungalow
Experience this charming 1940's cottage nestled on bustling Bohemia Avenue in the heart of picturesque Chesapeake City. Enjoy porch-sitting "on the Avenue", or visit numerous local eclectic shops, restaurants, a brew pub, and even a yoga studio, all only steps away. Marvel at massive cargo ships navigating the C&D Canal, just a 2-minute walk from your doorstep. Plenty of room for 4 guests. Private off street parking for 2 cars.
$171 per night
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Stay near Chesapeake City's top sights

Photo of Chesapeake Inn Restaurant & Marina
Chesapeake Inn Restaurant & Marina43 locals recommend
Photo of Schaefer's Canal House
Schaefer's Canal House33 locals recommend
Photo of The Bayard House Restaurant
The Bayard House Restaurant17 locals recommend
Photo of Tap Room Inc
Tap Room Inc8 locals recommend
Photo of Prime 225
Prime 22520 locals recommend
Photo of M/V Bay Breeze
M/V Bay Breeze5 locals recommend

Other great vacation rentals in Chesapeake City

Rental unit in Chesapeake City
Chesapeake Charm in Historic Chesapeake City, MD
$140 per night
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Rental unit in Chesapeake City
Stylish 2 bdrm haven in a historic canal town
$179 per night
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Private room in Elkton
Country Get Away 1 Bedroom Apartment
$71 per night
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Rental unit in Chesapeake City
Chesapeake City Great House Farm apartment
$130 per night
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Rental unit in Chesapeake City
The Checkered Rabbit
$225 per night
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Guesthouse in Chesapeake City
High-End Cottage, Water View, Chesapeake City, MD
$199 per night
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Cottage in North East
Cottage Just Off North East's Main Street
$88 per night
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Rental unit in Chesapeake City
Tranquility
$135 per night
Home in Elkton
Serene Hideaway
$135 per night
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Home in Elkton
Waterfront House on the Upper Chesapeake Bay
$152 per night
Guest suite in Middletown
Below the canal cottage suite!
$91 per night
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Home in North East
Historic Creekside Home - 2br 2.5ba Downtown
$145 per night
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