
Waterfront vacation rentals in Chesapeake
Find and book unique waterfront rentals on Airbnb
Top-rated waterfront rentals in Chesapeake
Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chesapeake waterfront rentals
Waterfront apartment rentals

Serene Tree House Retreat | Spacious 1br/1bth Home

Better at the Bay

Comfy 1BR w pond view Kingsmill

VB. Oceanfront/ Boardwalk,Beach, Pool, Balcony

Yorktown on the Waterfront

The Coastal Studio

Sandbridge Beach Bay Getaway

Tree Top Beach Bungalow 3 1/2 blocks fr beach
Waterfront house rentals

The Canary Island … Keep Calm and Fish On

5-Acre Getaway close to Historic Triangle

Waterfront House on the Bay/River

Steps to Beach at Chics Beach! Sleeps 12 & Garage!

PETS Welcome! 4Bed Beach View Privately Managed

*Semi-Priv Beach*King Bed* Waterfront*EV Charger

York River | Chesapeake Bay Bliss: Fishing Retreat

Escape to the water!
Waterfront condo rentals

Bay Breeze At Ocean View Beach Home

The Port - Large condo on Mason Avenue!

Beachfront Getaway, Pet Friendly, Mermaid Suite

Ocean & Bay Views - Local Family Owned & Operated

Oceanfront, beach, boardwalk, fun, dolphin, sunris

2 Bedroom Stylish Kingsmill condo

Oceanfront Modern Condo | Steps to Beach & Pool

Luxury Riverfront Condo w/ sunrise & sunset views
Quick stats about waterfront rentals in Chesapeake
Total rentals
70 properties
Nightly prices starting at
€ 25 before taxes and fees
Total number of reviews
3.4K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
10 properties have a pool
Destinations to explore
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- 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
- Kingsmill Resort
- Grandview Beach
- Haven Beach
- Currituck Beach Lighthouse
- Jamestown Settlement
- Outlook Beach
- Ocean Breeze Waterpark
- Virginia Beach National Golf Club
- Norfolk Botanical Garden
- Sarah Constant Beach Park
- Bonito St. Public Beach Access
- Grove Beach
- Kiptopeke Beach
- Little Creek Beach
- Golden Horseshoe Golf Club