
Condo holiday rentals in Chesapeake
Find and book unique condos on Airbnb
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

Beach Luxury Beachfront

Beachside Condo | 2BR/2BA | Cross street to beach!

1 Block to Oceanfront & Boardwalk

2BD2BA Condo w/Pool2Blocks2Beach

Good Vibes at the Beach

CLEAN Spacious Getaway near Beaches/Attractions+++

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

Beach Studio - Oceanside, Pool, Boardwalk, Bikes
Pet-friendly condo rentals

New Beachside Villa: Steps to Sand, Dog-Friendly!

Beachfront Getaway, Pet Friendly, Mermaid Suite

Ocean Bliss: Cozy Apt Retreat(D)

*New*OceansideCondo PetsOK Pool GameRoom No Stairs

Oyster & Pearl Beautiful New Single Level Condo

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

Walk to Corolla Village and the Beach!

CrabaCabana in the Center of Corolla
Condo rentals with a pool

Beach Please! 2 bedroom Single Level

Sandbridge Beach - DeepSeaSide Retreat

Ocean Breeze: New Condo Steps to the Beach

2BD/2BA Villa across Currituck Beach Lighthouse

Back Bay Breeze

Seas The Day of Virginia Beach

The Great Crabsby: A modern gem in Corolla's heart

Colonial Williamsburg Spacious 4 Bedroom Suite!
Quick stats about condo rentals in Chesapeake
Total rentals
40 properties
Nightly prices starting at
$84 NZD 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
- 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
- Charlotte Holiday rentals
- Ocean City Holiday rentals
- Virginia Beach Holiday rentals
- Jersey City Holiday rentals
- Cape Fear River Holiday rentals
- Rentals with a hot tub Chesapeake
- Rentals with a fire pit Chesapeake
- Rentals with breakfast Chesapeake
- Rentals with beach access Chesapeake
- Cottage rentals Chesapeake
- Mansion rentals Chesapeake
- Private suite rentals Chesapeake
- Fitness-friendly rentals Chesapeake
- Apartment rentals Chesapeake
- Rentals with a fireplace Chesapeake
- Rentals with lake access Chesapeake
- Kid-friendly rentals Chesapeake
- Rentals with a patio Chesapeake
- Pet-friendly rentals Chesapeake
- Beach house rentals Chesapeake
- Rentals with an EV charger Chesapeake
- Rentals with a kayak Chesapeake
- Rentals with a washing machine and dryer Chesapeake
- Waterfront rentals Chesapeake
- Family-friendly rentals Chesapeake
- Rentals with outdoor seating Chesapeake
- Rentals with pools Chesapeake
- Beachfront rentals Chesapeake
- Townhouse rentals Chesapeake
- House rentals Chesapeake
- Condo rentals Virginia
- Cabins United States
- Treehouses United States
- Tiny Houses United States
- Beach Houses United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Virginia Beach Oceanfront
- Carova Beach
- Corolla Beach
- Resort Beach
- Busch Gardens Williamsburg
- Buckroe Beach
- Water Country USA
- Kingsmill Resort
- First Landing State Park
- Buckroe Beach and Park
- Grandview Beach
- Haven Beach
- Outlook Beach
- Ocean Breeze Waterpark
- Jamestown Settlement
- Kiptopeke Beach
- Currituck Beach Lighthouse
- Virginia Beach National Golf Club
- Sarah Constant Beach Park
- Norfolk Botanical Garden
- Wilkins Beach
- Little Creek Beach
- Cape Charles Beachfront
- Golden Horseshoe Golf Club