Chesapeake Vacation Rentals

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Vacation Rentals in Chesapeake

Cozy Beach Cottage - Oceanview Walk To The Beach & Pet Friendly

Norfolk VA

$313 nightly

$363 total

Sep 30 - Oct 1

Total with taxes and fees

With a stay at this vacation home in Norfolk (Bayview), you'll be a 1-minute drive from Chesapeake Bay and 9 minutes from Naval Station Norfolk.

Kitchen

Washer

Your own private beach with this charming 3-bedroom beachfront house!

Norfolk VA

With a stay at this vacation home in Norfolk (Cottage Line), you'll be a 1-minute drive from Chesapeake Bay and 9 minutes from Naval Station Norfolk.

Kitchen

Washer

Bright 3-bedroom beach house with AC in charming Norfolk

Norfolk VA

With a stay at this vacation home in Norfolk (Willoughby Spit), you'll be a 1-minute drive from Chesapeake Bay and 9 minutes from Hampton University.

Kitchen

Washer

5 Minutes to the Casino!Family sized home 3 bedroom with patio and a game room

Portsmouth VA

With a stay at this vacation home, you'll be centrally located in Portsmouth, within a 15-minute drive of Waterside District and Norfolk State University.

Kitchen

Washer

Historic Old Towne Southern Charm

Portsmouth VA

With a stay at this vacation home in Portsmouth, you'll be within a 10-minute drive of Waterside District and Norfolk State University.

Kitchen

Washer

Spacious 4-bedroom house in beautiful 4x4 area of Corolla with ocean views!

corolla NC

Located in Corolla, this vacation home is by the ocean, a 2-minute drive from Carova Beach and 7 minutes from Currituck National Wildlife Refuge.

Kitchen

Washer

Oceanfront Beach Estate / Pool / Hot Tub / Arcade

Virginia Beach VA

With a stay at this vacation home in Virginia Beach (Sandbridge), you'll be a 1-minute drive from Sandbridge Beach and 7 minutes from Lake Tecumseh.

Pool

Hot Tub

Sandbridge... Beautiful Beach Home With Direct Beach Access and Ocean Views

Virginia Beach VA

With a stay at this vacation home in Virginia Beach (Sandbridge), you'll be a 1-minute drive from Sandbridge Beach and 7 minutes from Lake Tecumseh.

Pool

Kitchen

Cozy Ocean Side Cottage 89th St VA Beach- 20% discount Aug 25 – Sept 3, 2026

Virginia Beach VA

With a stay at this vacation home in Virginia Beach (Northeast Virginia Beach), you'll be within a 5-minute walk of First Landing State Park and Chesapeake Bay.

Kitchen

Washer

Big Waterfront House! Fishing Dock, Arcade, Garage Parking, Walk to Beach!

Norfolk VA

$528 nightly

$610 total

Oct 3 - Oct 4

Total with taxes and fees

With a stay at this vacation home in Norfolk (Willoughby Spit), you'll be a 2-minute drive from Chesapeake Bay and 9 minutes from Naval Station Norfolk.

Washer

Dryer

Fantastic home in the heart of the VB Resort Area Walk to Beach, Boardwalk.

Virginia Beach VA

Located in Virginia Beach (Northeast Virginia Beach), this vacation home is within a 15-minute walk of Virginia Beach Boardwalk and Neptune Statue.

Kitchen

Washer

Beachside Home • Fenced Yard • Dogs Welcome

Norfolk VA

With a stay at this vacation home in Norfolk (East Ocean View), you'll be within a 15-minute drive of Naval Station Norfolk and Chesapeake Bay.

Kitchen

Washer

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.