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
Apartment in West Grove
4.98 out of 5 average rating, 181 reviewsSwallow's Rest: East
Jul 4 – 11
Home in Elkton
4.83 out of 5 average rating, 323 reviewsCozy Cottage Elkton North East 3bed 2 bath Patio
Jan 30 – Feb 6
Guest suite in Chestertown
4.99 out of 5 average rating, 191 reviewsBeautiful Waterfront Chestertown Getaway
Oct 1 – 8
Guesthouse in Media
4.96 out of 5 average rating, 470 reviewsStudio Apartment in Attractive Sylvan Setting
Sep 11 – 18
Apartment in Chesapeake City
4.92 out of 5 average rating, 66 reviewshygge haven: hygge= happy + cozy
Nov 25 – Dec 2
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
Oct 15 – 22
Home in Newark
4.83 out of 5 average rating, 6 reviewsWhite Clay Creek Cottage
Mar 24 – 31
Other great vacation rentals in Chesapeake City
Home in Chesapeake City
5.0 out of 5 average rating, 16 reviewsMcReynolds-Woods House -Private 3 Bedroom Home
Dec 7 – 14
Apartment in Elkton
4.98 out of 5 average rating, 53 reviewsShort Term Water Oriented Furnished Apartment
Jul 28 – Aug 4
Cottage in Charlestown
4.98 out of 5 average rating, 51 reviewsLong Beach Cottage, (romantic couple’s getaway)
Sep 17 – 24
Home in Chesapeake City
5.0 out of 5 average rating, 80 reviewsSpring Season @ Old Lock View Chesapeake City MD
Nov 17 – 24
Guest suite in Newark
5.0 out of 5 average rating, 57 reviewsInviting, comfortable & private suite near Univ.
Sep 6 – 13
Guest suite in Chesapeake City
5.0 out of 5 average rating, 75 reviewsBenson House on Bohemia Ave (Back Deck)
Aug 28 – Sep 4
Guesthouse in Newark
5.0 out of 5 average rating, 30 reviewsCharming Fully Equipped Private Guesthouse
Jul 16 – 23
Home in Chesapeake City
4.96 out of 5 average rating, 25 reviewsHOOK WINE & SINKER sleeps 14 w/ Boat Slip and Inn
Oct 10 – 17
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
ﺩ.ﺇ220 before taxes and fees
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