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
Guest suite in Chesapeake
4.99 out of 5 average rating, 140 reviewsBeautiful Two Bedroom King Bed Guest House
Guest favourite
Guesthouse in Yorktown
4.97 out of 5 average rating, 209 reviewsCharming Yorktown Battlefield Cottage
Guest favourite
Home in Smithfield
4.97 out of 5 average rating, 209 reviewsMason Manor - Downtown Smithfield next to WCP
Guest favourite
Apartment in Portsmouth
4.96 out of 5 average rating, 243 reviewsCozy Ground Floor Apt in Historic Home
Guest favourite
Villa in Norfolk
4.94 out of 5 average rating, 145 reviews8 minutes walking from Sarah Constant Beach Park
Guest favourite
Cottage in Norfolk
4.98 out of 5 average rating, 181 reviewsPeaceful beach @Courtyard Cottage+No Cleaning Fee!
Guest favourite
Apartment in Newport News
4.97 out of 5 average rating, 153 reviewsCentrally Located Sleek Studio Apartment
Guest favourite
Home in Virginia Beach
4.92 out of 5 average rating, 264 reviewsMaster bedroom suite 3 blocks from the beach
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
- Outer Banks Vacation rentals
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- Smoking-friendly rentals Chesapeake
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