Holiday houses in Chesapeake
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Top-rated holiday rentals in Chesapeake
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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
Guesthouse in Yorktown
Charming Yorktown Battlefield Cottage
Guest favourite
Rental unit in Newport News
Centrally Located Sleek Studio Apartment
Guest favourite
Home in Norfolk
The Cozy Beach House
Guest favourite
Cottage in Norfolk
Lovely Ocean View Cottage
Guest favourite
Home in Smithfield
Mason Manor - Downtown Smithfield next to WCP
Guest favourite
Rental unit in Virginia Beach
Va.Beach/Oceanfront Studio, Boardwalk, Beach, Pool
Guest favourite
Guest suite in Carrollton
2BR 1BA Spacious Guest Suite, Woods & Water Views
Guest favourite
Cottage in East Ocean View
Peaceful beach @Courtyard Cottage+No Cleaning Fee!
Quick stats about accommodation 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 Accommodation & holiday rentals
- Virginia Beach Holiday rentals
- Richmond Accommodation & holiday rentals
- Norfolk Holiday rentals
- Williamsburg Accommodation & holiday rentals
- Nags Head Holiday rentals
- Myrtle Beach Accommodation & holiday rentals
- Washington Holiday rentals
- Deep Creek Lake Holiday rentals
- Philadelphia Accommodation & holiday rentals
- New York Accommodation & holiday rentals
- Jersey City Holiday rentals
- Family-friendly rentals Chesapeake
- Rentals with lake access Chesapeake
- Condo rentals Chesapeake
- Rentals with a hot tub Chesapeake
- Rentals with beach access Chesapeake
- Rentals with pools Chesapeake
- Fitness-friendly rentals Chesapeake
- Rentals with a fireplace Chesapeake
- Rentals with a home theatre Chesapeake
- Rentals with a fire pit Chesapeake
- Rentals with an EV charger Chesapeake
- Townhouse rentals Chesapeake
- Rentals with breakfast Chesapeake
- Smoking-friendly rentals Chesapeake
- Kid-friendly rentals Chesapeake
- Rentals with a patio Chesapeake
- Pet-friendly rentals Chesapeake
- Rentals with a washing machine and dryer Chesapeake
- Private suite rentals Chesapeake
- Apartment rentals Chesapeake
- Monthly Rentals Chesapeake
- Waterfront rentals Chesapeake
- House rentals Chesapeake
- Rentals with outdoor seating Chesapeake
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