Vacation rentals in Chesapeake
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Top-rated vacation rentals in Chesapeake
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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, 364 reviewsThe Nook
Guest favourite
Apartment in Newport News
4.97 out of 5 average rating, 151 reviewsCentrally Located Sleek Studio Apartment
Superhost
Tiny homes in Chesapeake
4.81 out of 5 average rating, 131 reviewsRural Tiny House in the Edge Of the Woods
Guest favourite
Place to stay in Virginia Beach
4.99 out of 5 average rating, 119 reviewsSalty Willow-a “suite retreat” in the heart of VB!
Guest favourite
Home in Smithfield
4.97 out of 5 average rating, 208 reviewsMason Manor - Downtown Smithfield next to WCP
Guest favourite
Guesthouse in Hampton
4.99 out of 5 average rating, 292 reviewsSun Sea and Sand
Guest favourite
Guesthouse in Portsmouth
4.97 out of 5 average rating, 151 reviewsSpring Hill Guest Cottage - Portsmouth
Guest favourite
Guest suite in Chesapeake
4.99 out of 5 average rating, 137 reviewsBeautiful Two Bedroom King Bed Guest House
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
- Virginia Beach Vacation rentals
- Richmond Vacation rentals
- Norfolk Vacation rentals
- Williamsburg Vacation rentals
- Nags Head Vacation rentals
- Myrtle Beach Vacation rentals
- Washington Vacation rentals
- Deep Creek Lake Vacation rentals
- Philadelphia Vacation rentals
- Jersey City Vacation rentals
- New York Vacation rentals
- Rentals with a firepit Chesapeake
- Rentals with a fireplace Chesapeake
- Rentals with pools Chesapeake
- Fitness-friendly rentals Chesapeake
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- Family-friendly rentals Chesapeake
- Kid-friendly rentals Chesapeake
- Rentals with a patio Chesapeake
- Pet-friendly rentals Chesapeake
- Rentals with a home theater 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 washer and dryer Chesapeake
- Apartment rentals Chesapeake
- Monthly Rentals Chesapeake
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