Holiday rentals in Chesapeake Beach
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Top-rated holiday rentals in Chesapeake Beach
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
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Popular amenities for Chesapeake Beach holiday rentals
Other great holiday rentals in Chesapeake Beach
Guest favourite
Guest suite in Chesapeake Beach
4.95 out of 5 average rating, 82 reviewsNice Guest Suite at Chesapeake Bay
22–29 Oct
$190 SGD per night
Guest favourite
Cottage in North Beach
4.95 out of 5 average rating, 77 reviewsQuiet Coastal Cottage Escape with Water Views
6–13 Aug
$232 SGD per night
Guest favourite
Serviced apartment in Huntingtown
4.89 out of 5 average rating, 18 reviewsPrivate Apartment On An Animal Sanctuary
26 May – 2 Jun
$141 SGD per night
Guest favourite
Guest house in Chesapeake Beach
4.81 out of 5 average rating, 98 reviews“THE CRAB SHACK” BEACH COTTAGE CLOSE TO THE BAY
20–27 Jul
$108 SGD per night
Guest favourite
Home in North Beach
4.91 out of 5 average rating, 23 reviewsLarge Bungalow 2 Blocks to Beach
29 May – 5 Jun
$245 SGD per night
Guest favourite
Home in North Beach
4.97 out of 5 average rating, 60 reviewsCharming Herrington / Rose Haven Cottage
29 Sep – 6 Oct
$248 SGD per night
Guest favourite
Cottage in Chesapeake Beach
5.0 out of 5 average rating, 11 reviewsPrivate Bay Cottage Cliffside (pet friendly)
26 Sep – 3 Oct
$386 SGD per night
Guest favourite
Guest house in Saint Leonard
4.98 out of 5 average rating, 80 reviewsStudio on the Bay.
31 Dec – 7 Jan
$164 SGD per night
Destinations to explore
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