Holiday houses in Chesapeake
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Top-rated holiday rentals in Chesapeake
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesapeake holiday rentals
Other great holiday rentals in Chesapeake
Guest favourite
Cottage in Norfolk
4.98 out of 5 average rating, 179 reviewsPeaceful beach @Courtyard Cottage+No Cleaning Fee!
Guest favourite
Guesthouse in Yorktown
4.97 out of 5 average rating, 208 reviewsCharming Yorktown Battlefield Cottage
Guest favourite
Apartment in Newport News
4.97 out of 5 average rating, 151 reviewsCentrally Located Sleek Studio Apartment
Guest favourite
Guesthouse in Hampton
4.99 out of 5 average rating, 291 reviewsSun Sea and Sand
Guest favourite
Apartment in Virginia Beach
4.88 out of 5 average rating, 154 reviewsVa.Beach/Oceanfront Studio, Boardwalk, Beach, Pool
Guest favourite
Home in Smithfield
4.97 out of 5 average rating, 208 reviewsMason Manor - Downtown Smithfield next to WCP
Guest favourite
Cottage in Norfolk
5.0 out of 5 average rating, 251 reviewsBeautiful Cottage Waterfront Near Downtown Norfolk
Guest favourite
Guesthouse in Portsmouth
4.97 out of 5 average rating, 151 reviewsSpring Hill Guest Cottage - Portsmouth
Quick stats about holiday 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 Holiday rentals
- Virginia Beach Holiday rentals
- Richmond Holiday rentals
- Norfolk Holiday rentals
- Williamsburg Holiday rentals
- Nags Head Holiday rentals
- Myrtle Beach Holiday rentals
- Washington Holiday rentals
- Deep Creek Lake Holiday rentals
- Philadelphia Holiday rentals
- Jersey City Holiday rentals
- New York Holiday rentals
- Rentals with a fire pit Chesapeake
- Rentals with a fireplace Chesapeake
- Rentals with pools Chesapeake
- Fitness-friendly rentals Chesapeake
- Private suite rentals Chesapeake
- Condo rentals Chesapeake
- Family-friendly rentals Chesapeake
- Kid-friendly rentals Chesapeake
- Rentals with a patio Chesapeake
- Pet-friendly rentals Chesapeake
- Rentals with a home theatre Chesapeake
- Rentals with lake access Chesapeake
- Rentals with a hot tub Chesapeake
- Rentals with beach access Chesapeake
- Rentals with breakfast Chesapeake
- House rentals Chesapeake
- Rentals with outdoor seating Chesapeake
- Waterfront rentals Chesapeake
- Rentals with an EV charger Chesapeake
- Smoking-friendly rentals Chesapeake
- Townhouse rentals Chesapeake
- Rentals with a washing machine and dryer Chesapeake
- Apartment rentals Chesapeake
- Monthly Rentals Chesapeake
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