Vacation rentals in Chesapeake
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Top-rated vacation rentals in Chesapeake
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Chesapeake vacation rentals
Other great vacation rentals in Chesapeake
Guest favourite
Apartment in Williamsburg
4.84 out of 5 average rating, 360 reviewsThe Nook
Jan. 2 – 9
$163 CAD per night
Guest favourite
Guesthouse in Yorktown
4.97 out of 5 average rating, 202 reviewsCharming Yorktown Battlefield Cottage
Jul. 8 – 15
$175 CAD per night
Guest favourite
Apartment in Chesapeake
5.0 out of 5 average rating, 29 reviewsEntire Apartment - No Cleaning Fees!
Oct. 14 – 21
$155 CAD per night
Guest favourite
Apartment in Chesapeake
4.95 out of 5 average rating, 41 reviewsBlissful Nook @ Washington
Aug. 19 – 26
$175 CAD per night
Guest favourite
Apartment in Chesapeake
4.89 out of 5 average rating, 19 reviewsWarm Luxury unit Central Greenbrier
Jan. 18 – 25
$237 CAD per night
Guest favourite
Home in Norfolk
5.0 out of 5 average rating, 22 reviewsStylish Beach House, Hot Tub, Pet Friendly
Feb. 17 – 24
$240 CAD per night
Guest favourite
Bungalow in Chesapeake
4.93 out of 5 average rating, 72 reviewsPrivate and Cozy Bungalow Loaded with Amenities
May 13 – 20
$188 CAD per night
Guest favourite
Guest suite in Chesapeake
4.91 out of 5 average rating, 46 reviewsGuest Suite with Private entrance & bathroom
Aug. 11 – 18
$186 CAD per night
Quick stats about vacation rentals in Chesapeake
Total rentals
1.1K properties
Rentals with dedicated workspaces
590 properties have a dedicated workspace
Rentals with a pool
150 properties have a pool
Pet-friendly rentals
340 properties allow pets
Family-friendly rentals
510 properties are a good fit for families
Total number of reviews
31K reviews
Destinations to explore
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- Rentals with a patio Chesapeake
- Kid-friendly rentals Chesapeake
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- Rentals with pools Chesapeake
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- Monthly Rentals Chesapeake
- Rentals with a hot tub Chesapeake
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