Skip to content

Chesapeake vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Chesapeake

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

SUPERHOST
  1. Private room
  2. Great Bridge
Welcome Aboard! Relaxation awaits!

NO CLEANING FEE! New home. Private side entrance to your personal paradise. Your suite is a lock-off from the main home. Private bedroom connected to your private bathroom with attached dining space. Dining space includes mini-fridge with freezer, microwave, Keurig coffee maker and table for two. Access to backyard and patio with furniture. No kitchen and no laundry on site. Centrally located in Great Bridge Chesapeake with several options for grocery, dining, shopping, laundry, beach and more.

$57 per night
SUPERHOST
  1. Private room
  2. Virginia Beach
Private Bedroom Centrally Located.

Private Bedroom with Bath 20 minutes to Virginia Beach Oceanfront and Norfolk International Airport.

$50 per night
SUPERHOST
  1. Private room
  2. Virginia Beach
Tropic Napper

The room has a tropical, beachy feel. Room-darkening curtains paired with a 3-inch memory form mattress topper atop a queen-sized bed is the perfect recipe for sleep. You'll also have a TV equipped with an Amazon Firestick. Everything in the house is labeled so you and your temporary housemates know where to comfortably put your things outside your room The location is 20 minutes from the beach, walking distance to a Wawa and a Wafflehouse and an international store.

$50 per night

Vacation rentals for every style

Get the amount of space that is right for you

  • Homes
  • Hotels
  • Unique stays

Other great vacation rentals in Chesapeake

  1. Private room
  2. Great Bridge
Full of natural light private bedroom
$59 per night
  1. Entire rental unit
  2. Norfolk
Little Victoria in Norfolk
$50 per night
SUPERHOST
  1. Private room
  2. Virginia Beach
One bedroom in a single family house with home gym
$50 per night
  1. Private room
  2. Chesapeake
Spacious In Law Master Suite
$70 per night
SUPERHOST
  1. Entire guest suite
  2. Virginia Beach
Guest suite with kitchenette, Private bath.
$79 per night
SUPERHOST
  1. Entire guest suite
  2. Chesapeake
Sweet Suite!
$109 per night
SUPERHOST
  1. Private room
  2. Chesapeake
Beautiful family's home close to downtown Norfolk
$51 per night
  1. Private room
  2. Chesapeake
Cozy and Sparkling Room in Chesapeake 2
$41 per night
  1. Private room
  2. Virginia Beach
A Nice and Comfortable Room in Virginia Beach
$30 per night
SUPERHOST
  1. Entire guesthouse
  2. Chesapeake
Beautiful and Chic, One Room Studio Apartment
$104 per night
  1. Entire townhouse
  2. Chesapeake
One bedroom townhouse in Greenbrier Chesapeake
$86 per night
SUPERHOST
  1. Private room
  2. Virginia Beach
Cozy Hideout
$50 per night