Chesapeake City vacation rentals
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Top-rated vacation rentals in Chesapeake City
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesapeake City vacation rentals
Other great vacation rentals in Chesapeake City
Guesthouse in Quarryville
4.99 out of 5 average rating, 235 reviewsThe Olde Wash House on Camargo
Jan 1 – 8
Apartment in West Grove
4.98 out of 5 average rating, 181 reviewsSwallow's Rest: East
Sep 29 – Oct 6
Guest suite in Chestertown
4.99 out of 5 average rating, 191 reviewsBeautiful Waterfront Chestertown Getaway
Sep 13 – 20
Guesthouse in Media
4.96 out of 5 average rating, 470 reviewsStudio Apartment in Attractive Sylvan Setting
Oct 9 – 16
Apartment in Chesapeake City
4.92 out of 5 average rating, 66 reviewshygge haven: hygge= happy + cozy
Feb 28 – Mar 7
Cottage in Chesapeake City
5.0 out of 5 average rating, 53 reviewsBohemia Bungalow
Sep 9 – 16
Home in Chesapeake City
5.0 out of 5 average rating, 29 reviewsCharming, updated home in Historic Chesapeake City
Dec 1 – 8
Home in Chesapeake City
5.0 out of 5 average rating, 24 reviewsWister Loft: Charm & History with Modern Love.
Apr 11 – 18
Other great vacation rentals in Chesapeake City
Apartment in Elkton
4.98 out of 5 average rating, 53 reviewsShort Term Water Oriented Furnished Apartment
Mar 25 – Apr 1
Home in Chesapeake City
5.0 out of 5 average rating, 80 reviewsSpring Season @ Old Lock View Chesapeake City MD
Jan 30 – Feb 6
Cottage in Charlestown
4.98 out of 5 average rating, 51 reviewsLong Beach Cottage, (romantic couple’s getaway)
Dec 17 – 24
Guest suite in Newark
5.0 out of 5 average rating, 57 reviewsInviting, comfortable & private suite near Univ.
Jul 27 – Aug 3
Guesthouse in Newark
5.0 out of 5 average rating, 30 reviewsCharming Fully Equipped Private Guesthouse
Sep 19 – 26
Guest suite in Chesapeake City
5.0 out of 5 average rating, 75 reviewsBenson House on Bohemia Ave (Back Deck)
Sep 28 – Oct 5
Home in Chesapeake City
4.96 out of 5 average rating, 25 reviewsHOOK WINE & SINKER sleeps 14 w/ Boat Slip and Inn
Oct 13 – 20
Apartment in Rising Sun
4.91 out of 5 average rating, 55 reviewsCozy Corner Getaway: Relax on an Amish Farm
Jan 30 – Feb 6
Quick stats about vacation rentals in Chesapeake City
Total rentals
20 properties
Wifi availability
20 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
1.2K reviews
Nightly prices starting at
€ 56 before taxes and fees
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