
Condo holiday rentals in Chesapeake
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Top-rated condo rentals in Chesapeake
Guests agree: These condos 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 condo rentals
Weekly condo rentals

Cozy 1 Bd condo, 1 block from the beach!

1 Block to Oceanfront & Boardwalk

Oceanfront & Brdwalk 1 blck away! Reduced for Fall

2BD2BA Condo w/Pool2Blocks2Beach

21st Street Condo - 1 block from the Dome

Cozy Retreat-1 BD Condo, 1 Block from Beach!

Beach Chic Remodeled Condo 1 Block from Beachfront

Kingsmill Resort Business Class - Great Monthly
Pet-friendly condo rentals

Beachfront Getaway, Pet Friendly, Mermaid Suite

Ocean Bliss: Cozy Apt Retreat(D)

Oyster & Pearl Beautiful New Single Level Condo

*New*OceansideCondo PetsOK Pool GameRoom No Stairs

Wonderful & tranquil beach retreat: 2BR/2BA Condo.

Walk to Corolla Village and the Beach!

Barefoot Bliss - Single Level Steps to the Beach

CrabaCabana in the Center of Corolla
Condo rentals with a pool

2 bdr: Steps to Sand, Dog-Friendly!

Beach Please! 2 bedroom Single Level

2BD/2BA Villa across Currituck Beach Lighthouse

Off The Hook-Luxury Cottage - Heart of Corolla!

Historic Powhatan resort 2 bdrm

Beach Studio - Oceanside, Pool, Boardwalk, Bikes

Seas The Day of Virginia Beach

Beach Quarters Resort Oceanfront - 1 bdrm (6)
Quick stats about condo rentals in Chesapeake
Total rentals
40 properties
Nightly prices starting at
$75 AUD before taxes and fees
Total number of reviews
1.2K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Destinations to explore
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- Rentals with beach access Chesapeake
- Rentals with breakfast Chesapeake
- Beachfront rentals Chesapeake
- Cottage rentals Chesapeake
- Rentals with a patio Chesapeake
- Pet-friendly rentals Chesapeake
- Smoking-friendly rentals Chesapeake
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- Rentals with outdoor seating Chesapeake
- Fitness-friendly rentals Chesapeake
- Rentals with a fireplace Chesapeake
- Apartment rentals Chesapeake
- Guesthouse rentals Chesapeake
- Rentals with a fire pit Chesapeake
- Rentals with lake access Chesapeake
- Beach house rentals Chesapeake
- Rentals with an EV charger Chesapeake
- Rentals with a washing machine and dryer Chesapeake
- Rentals with a kayak Chesapeake
- Rentals with a hot tub Chesapeake
- Rentals with pools Chesapeake
- Townhouse rentals Chesapeake
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- Condo rentals Virginia
- Condo rentals United States
- Virginia Beach Oceanfront
- Carova Beach
- Corolla Beach
- Busch Gardens Williamsburg
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Haven Beach
- Buckroe Beach and Park
- Kingsmill Resort
- Grandview Beach
- Jamestown Settlement
- Bethel Beach
- Kiptopeke Beach
- Outlook Beach
- Ocean Breeze Waterpark
- Virginia Beach National Golf Club
- Norfolk Botanical Garden
- Chrysler Museum of Art
- Cape Charles Beachfront
- Golden Horseshoe Golf Club
- James River Country Club
- Sarah Constant Beach Park
- Red Wing Lake Golf Course