Skip to content

Vacation rentals in Chesapeake

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Chesapeake

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest Apartment on the Lake
SUPERHOST
Entire guest suite · 2 guests · 1 bed · 1 bath

Guest Apartment on the LakePrivate 3 room Guest Apartment residing on a beautiful Lake! This peaceful, serene, retreat resides in a quite neighborhood in the heart of Virginia Beach, just 25 mins from the Ocean Front and 20 mins to Town Center. Our Lake is perfect for relaxing while watching the sunset and swimming on summer days! This home is situated at the center point of many of Virginia Beach's best attractions.

Charming Bedroom in Historic House!
SUPERHOST
Private room · 2 guests · 1 bed · 1 private bath

Charming Bedroom in Historic House!Your room is cozy and sheltered while looking into the branches of a beautiful oak tree. It is located on the top, third story of our home. A good night's sleep is very important to us, so we installed an ergonomic foam Nectar mattress and pillows. Your private bathroom is just down the hall from your room. We provide soap, shampoo, and conditioner, as well as towels.

Captain's Quarters-Pool Side Private Studio Apt
SUPERHOST
Private room · 2 guests · 1 bed · 1 private bath

Captain's Quarters-Pool Side Private Studio AptRoss's Retreat Located on the Northwest River branch of the ICW offers Three Unique Lodging Options. The Captains Quarters is our largest Private Access Studio Apartment available and is the only unit on the Ground Floor of the main House, This Pool Side Suite has its own Kitchen and spacious on-suite Bath Guests will also have access to gym, 2nd floor Veranda, Lanai and Sundeck. You can reserve time to Canoe, or Kayak, on premise.

Vacation rentals for every style

Get the amount of space that is right for you

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Chesapeake vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Chesapeake

  1. Entire rental unit
  2. Norfolk
The Redgate - Suite One
$72 per night
SUPERHOST
  1. Entire guest suite
  2. Virginia Beach
Suite D'Oiseaux
$90 per night
SUPERHOST
  1. Private room
  2. Chesapeake
Cozy & Quiet Room for Dog Lovers
$44 per night
SUPERHOST
  1. Private room
  2. Norfolk
Cheerful room in a nice area
$51 per night
  1. Entire rental unit
  2. Virginia Beach
THE PARADISE PLACE! ENTIRE 1 BDRM APT W/ BALCONY!
$169 per night
  1. Entire townhouse
  2. Virginia Beach
Peaceful & Cozy Getaway! Convenient location
$157 per night
SUPERHOST
  1. Entire guest suite
  2. Virginia Beach
*NEW* Virginia Beach Studio
$66 per night
SUPERHOST
  1. Private room
  2. Virginia Beach
Private Bedroom Centrally Located.
$48 per night
  1. Entire townhouse
  2. Norfolk
ODU Elite Suite: Cheerful 3 bedroom townhouse
$125 per night
SUPERHOST
  1. Entire guesthouse
  2. Norfolk
Private Guesthouse, Ghent/Downtown near ODU, EVMS
$104 per night
SUPERHOST
  1. Entire guest suite
  2. Chesapeake
Sweet Suite!
$86 per night
SUPERHOST
  1. Entire guest suite
  2. Chesapeake
King Guest Suite - A TOGAR Family Vacation Rental
$70 per night

Nearby destinations

Unique stays on Airbnb