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
Guest suite in Chesapeake
4.91 out of 5 average rating, 45 reviewsGuest Suite with Private entrance & bathroom
4 – 11 Sept
Townhouse in Chesapeake
4.97 out of 5 average rating, 29 reviewsCenter of Greenbrier
2 – 9 Sept
Home in Chesapeake
4.87 out of 5 average rating, 23 reviewsChesapeake. 3 Bedroom 1-1/2 Bath Small family home
21 – 28 Jan
Apartment in Chesapeake
4.89 out of 5 average rating, 18 reviewsWarm Luxury unit Central Greenbrier
25 Feb – 4 Mar
Apartment in Chesapeake
4.89 out of 5 average rating, 9 reviewsSerene Tree House Retreat | Spacious 1br/1bth Home
17 – 24 Nov
Bungalow in Chesapeake
4.93 out of 5 average rating, 71 reviewsPrivate and Cozy Bungalow Loaded with Amenities
1 – 8 May
Apartment in Chesapeake
4.94 out of 5 average rating, 16 reviewsCountry Escape - Next DOOR - Hidden Gem
27 Aug – 3 Sept
Campervan/RV in Chesapeake
4.84 out of 5 average rating, 88 reviewsWaterfront Airstream in peaceful central location!
1 – 8 May
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
- New York Holiday rentals
- Jersey City Holiday rentals
- Private suite rentals Chesapeake
- Rentals with a washing machine and dryer Chesapeake
- Rentals with an EV charger Chesapeake
- Rentals with a hot tub Chesapeake
- House rentals Chesapeake
- Family-friendly rentals Chesapeake
- Rentals with pools Chesapeake
- Monthly Rentals Chesapeake
- Rentals with beach access Chesapeake
- Rentals with lake access Chesapeake
- Rentals with a home theatre Chesapeake
- Fitness-friendly rentals Chesapeake
- Rentals with a fireplace Chesapeake
- Kid-friendly rentals Chesapeake
- Apartment rentals Chesapeake
- Waterfront rentals Chesapeake
- Smoking-friendly rentals Chesapeake
- Pet-friendly rentals Chesapeake
- Rentals with a fire pit Chesapeake
- Condo rentals Chesapeake
- Townhouse rentals Chesapeake
- Rentals with outdoor seating Chesapeake
- Rentals with breakfast Chesapeake
- Rentals with a patio Chesapeake
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