
House holiday rentals in Chesapeake
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Top-rated house rentals in Chesapeake
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Chesapeake
House rentals with a pool

THE OLD BEACON 1 | Beach Living

York River Vacation Home

The Blue Octopus~Private Pool~HotTub~Beach~FirePit

Paint The Beach Pink! Full House | Private Pool

Elegance Escape on Saunders Dr

Private Pool at the Oceanfront in a Spacious Home

Gorgeous Vacation House

Stunning Views of Back Bay & Seconds to the Beach
Weekly house rentals

Southern Charm Warm and Welcome

R & R River House

Beautiful Design Waterfront Home 12 min to Casino!

The Bird’s Nest

Home Away From Home

Cornick Corner near "Rivers Casino"

Hidden Gem.4/bedroom cozy home fenced in yard

Newport Nook: 5/2.5 Home in Norfolk - Sleeps 10!
Private house rentals

Cozy Modern Cabin

Private Beachfront Modern Villa: Outdoor Shower!

941 Coastal Luxury Retreat

Charming 3-Bdrm Gem! Sleeps 6, Near Casino & All.

Spacious home centrally located

Charming Coastal Escape

Tudor Treasure in Olde Towne

The Bartlett Inn
Quick stats about house rentals in Chesapeake
Total rentals
560 properties
Total number of reviews
13K reviews
Family-friendly rentals
280 properties are a good fit for families
Pet-friendly rentals
150 properties allow pets
Rentals with a pool
60 properties have a pool
Rentals with dedicated workspaces
310 properties have a dedicated workspace
Destinations to explore
- Virginia Beach Holiday rentals
- Williamsburg Holiday rentals
- Shanghai Holiday rentals
- Richmond Holiday rentals
- Myrtle Beach Holiday rentals
- Charlotte Holiday rentals
- Outer Banks Holiday rentals
- Washington Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Jersey Shore Holiday rentals
- New York Holiday rentals
- Mansion rentals Chesapeake
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- Cottage rentals Chesapeake
- Rentals with beach access Chesapeake
- Rentals with a firepit Chesapeake
- Rentals with breakfast Chesapeake
- Rentals with an EV charger Chesapeake
- Family-friendly rentals Chesapeake
- Rentals with a patio Chesapeake
- Pet-friendly rentals Chesapeake
- Rentals with a kayak Chesapeake
- Rentals with a hot tub Chesapeake
- Rentals with outdoor seating Chesapeake
- Flat rentals Chesapeake
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- Beachfront rentals Chesapeake
- Rentals with a washing machine and dryer Chesapeake
- Beach house rentals Chesapeake
- Rentals with lake access Chesapeake
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- Virginia Beach Oceanfront
- Carova Beach
- Resort Beach
- Corolla Beach
- Busch Gardens Williamsburg
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Buckroe Beach and Park
- Grandview Beach
- Kingsmill Resort
- Outlook Beach
- Haven Beach
- Jamestown Settlement
- Currituck Beach Lighthouse
- Ocean Breeze Waterpark
- Sarah Constant Beach Park
- Virginia Beach National Golf Club
- Norfolk Botanical Garden
- Kiptopeke Beach
- Wilkins Beach
- Golden Horseshoe Golf Club
- Bonito St. Public Beach Access
- Little Creek Beach