Holiday houses in Chesapeake
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Top-rated holiday rentals in Chesapeake
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Holiday rentals for every style
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Popular amenities for Chesapeake holiday rentals
Other great holiday rentals in Chesapeake
Barn in Virginia Beach
4.79 out of 5 average rating, 831 reviewsCozy craftsman barn near the bay!
8 – 15 Apr
Apartment in Newport News
4.97 out of 5 average rating, 148 reviewsCentrally Located Sleek Studio Apartment
3 – 10 Dec
Cottage in Norfolk
5.0 out of 5 average rating, 250 reviewsBeautiful Cottage Waterfront Near Downtown Norfolk
4 – 11 Sept
Guesthouse in Yorktown
4.97 out of 5 average rating, 203 reviewsCharming Yorktown Battlefield Cottage
28 Sept – 5 Oct
Home in Smithfield
4.97 out of 5 average rating, 205 reviewsMason Manor - Downtown Smithfield next to WCP
17 – 24 Apr
Guest suite in Carrollton
4.98 out of 5 average rating, 161 reviews2BR 1BA Spacious Guest Suite, Woods & Water Views
3 – 10 Sept
Home in Norfolk
4.92 out of 5 average rating, 155 reviews@Whit’s End? Come in and Relax
8 – 15 Nov
Guest suite in Virginia Beach
4.85 out of 5 average rating, 173 reviewsSmall & Cozy Guest Suite w/ Private Bath & Jet-Tub
21 – 28 June
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
- Jersey City Holiday rentals
- New York Accommodation & holiday rentals
- Rentals with pools Chesapeake
- Rentals with a fireplace Chesapeake
- Condo rentals Chesapeake
- Rentals with an EV charger Chesapeake
- Rentals with a patio Chesapeake
- Smoking-friendly rentals Chesapeake
- Rentals with breakfast Chesapeake
- Waterfront rentals Chesapeake
- Rentals with a hot tub Chesapeake
- Rentals with a fire pit Chesapeake
- Rentals with beach access Chesapeake
- Rentals with lake access Chesapeake
- Family-friendly rentals Chesapeake
- Rentals with a washing machine and dryer Chesapeake
- Fitness-friendly rentals Chesapeake
- Private suite rentals Chesapeake
- House rentals Chesapeake
- Monthly Rentals Chesapeake
- Townhouse rentals Chesapeake
- Kid-friendly rentals Chesapeake
- Rentals with outdoor seating Chesapeake
- Rentals with a home theatre Chesapeake
- Pet-friendly rentals Chesapeake
- Apartment rentals Chesapeake
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