
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
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Popular amenities for Chesapeake holiday rentals
Other great holiday rentals in Chesapeake
Superhost

Private room in Chesapeake
4.86 out of 5 average rating, 88 reviewsPrivate Entrance, Spacious Master Bedroom Suite
Guest favourite

Private room in Virginia Beach
4.89 out of 5 average rating, 79 reviewsRoom for rent 10 miles from the beach
Superhost

Private room in Ballentine Place
4.92 out of 5 average rating, 13 reviewsComfortable Room w/ Queen Bed
Guest favourite

Private room in Suffolk
4.9 out of 5 average rating, 20 reviewsRanch in Heart of Suffolk (BR#1)
Top Guest favourite

Private room in Virginia Beach
5 out of 5 average rating, 30 reviewsGolf Course Getaway
Top Guest favourite

Private room in Chesapeake
5 out of 5 average rating, 14 reviewsCozy room, Clean & Affordable!
Superhost

Private room in Chesapeake
4.5 out of 5 average rating, 4 reviewsFirst Floor Guestroom
Guest favourite

Private room in Suffolk
4.93 out of 5 average rating, 29 reviewsQuiet Condo-Suffolk Home with a View
Quick stats about holiday rentals in Chesapeake
Total rentals
970 properties
Nightly prices starting at
$17 NZD before taxes and fees
Total number of reviews
36K reviews
Family-friendly rentals
440 properties are a good fit for families
Pet-friendly rentals
300 properties allow pets
Rentals with a pool
130 properties have a pool
Destinations to explore
- New York City Holiday rentals
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- North Myrtle Beach Holiday rentals
- Family-friendly rentals Chesapeake
- Townhouse rentals Chesapeake
- Beach house rentals Chesapeake
- Rentals with a fire pit Chesapeake
- Rentals with a washing machine and dryer Chesapeake
- Rentals with pools Chesapeake
- Mansion rentals Chesapeake
- Private suite rentals Chesapeake
- House rentals Chesapeake
- Rentals with a hot tub Chesapeake
- Rentals with lake access Chesapeake
- Condo rentals Chesapeake
- Rentals with beach access Chesapeake
- Cottage rentals Chesapeake
- Rentals with outdoor seating Chesapeake
- Smoking-friendly rentals Chesapeake
- Waterfront rentals Chesapeake
- Fitness-friendly rentals Chesapeake
- Beachfront rentals Chesapeake
- Rentals with an EV charger Chesapeake
- Rentals with a kayak Chesapeake
- Apartment rentals Chesapeake
- Guesthouse rentals Chesapeake
- Rentals with a fireplace Chesapeake
- Rentals with a patio Chesapeake
- Pet-friendly rentals Chesapeake
- Rentals with breakfast Chesapeake
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Corolla Beach
- Carova Beach
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Kingsmill Resort
- Haven Beach
- Buckroe Beach and Park
- Grandview Beach
- Jamestown Settlement
- Bethel Beach
- Kiptopeke Beach
- Outlook Beach
- Ocean Breeze Waterpark
- Virginia Beach National Golf Club
- Norfolk Botanical Garden
- Cape Charles Beachfront
- Golden Horseshoe Golf Club
- Chrysler Museum of Art
- Wilkins Beach
- James River Country Club
- Little Creek Beach