
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 Chesapeake house rentals
House rentals with a pool

THE OLD BEACON 1 | Beach Living

Paint The Beach Pink! Full House | Private Pool

Country Comfort Close to the Beaches

Private Pool at the Oceanfront in a Spacious Home

Gorgeous Vacation House

Stunning Views of Back Bay & Seconds to the Beach

Perfect Getaway!

Sunrise, North End Beach
Weekly house rentals

Relax & Play Awhile~Games~SAUNA~Massage Chair

10 min to Ocean View: BBQ | Volleyball| Fire Pit

The Bartlett Inn

Beach Stay

Backyard Bungalow | Near Beach

Quiet & Private, Comfy Beds, Fire Pit, & Bikes

Hidden Gem.4/bedroom cozy home fenced in yard

Casa del Mar - Bold, Bright & Steps to the Sand!
Private house rentals

*Escape to Beach Dream*

Cozy Modern Cabin

941 Coastal Luxury Retreat

Home Away From Home

Cozy 3BD Beachfront | Foosball & Yard Games w/ BBQ

Eden Lake House Cape Charles

Surf Cafe~Backyard Oasis~King Bed~2 mins to Beach!

The Booker: Modern Retreat by the Beach
Quick stats about house rentals in Chesapeake
Total rentals
540 properties
Total number of reviews
14K 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
290 properties have a dedicated workspace
Destinations to explore
- New York City Holiday rentals
- Washington Holiday rentals
- Myrtle Beach Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- Outer Banks Holiday rentals
- South Jersey Holiday rentals
- Ocean City Holiday rentals
- Charlotte Holiday rentals
- Virginia Beach Holiday rentals
- Jersey City Holiday rentals
- Cape Fear River Holiday rentals
- Mansion rentals Chesapeake
- Private suite rentals Chesapeake
- Waterfront rentals Chesapeake
- Beach house rentals Chesapeake
- Townhouse rentals Chesapeake
- Rentals with a washing machine and dryer Chesapeake
- Rentals with a kayak Chesapeake
- Cottage rentals Chesapeake
- Rentals with outdoor seating Chesapeake
- Family-friendly rentals Chesapeake
- Rentals with a fireplace Chesapeake
- Condo rentals Chesapeake
- Rentals with beach access Chesapeake
- Fitness-friendly rentals Chesapeake
- Rentals with lake access Chesapeake
- Apartment rentals Chesapeake
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- Rentals with a hot tub Chesapeake
- Rentals with a patio Chesapeake
- Pet-friendly rentals Chesapeake
- Rentals with a fire pit Chesapeake
- Beachfront rentals Chesapeake
- Rentals with an EV charger Chesapeake
- Rentals with pools Chesapeake
- Rentals with breakfast Chesapeake
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- Virginia Beach Oceanfront
- Carova Beach
- Corolla Beach
- Busch Gardens Williamsburg
- Buckroe Beach
- Water Country USA
- Kingsmill Resort
- First Landing State Park
- Buckroe Beach and Park
- Haven Beach
- Grandview Beach
- Kiptopeke Beach
- Jamestown Settlement
- Outlook Beach
- Ocean Breeze Waterpark
- Virginia Beach National Golf Club
- Norfolk Botanical Garden
- Sarah Constant Beach Park
- Cape Charles Beachfront
- Golden Horseshoe Golf Club
- James River Country Club
- Red Wing Lake Golf Course
- Chrysler Museum of Art
- Little Creek Beach