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.

Private room in Chesapeake
Immaculate Room in Luxury Highrise
Enjoy a stylish experience at the newest urban lifestyle community in Coastal Virginia. Everything is close by...Walk to restaurants...literally downstairs. Lots of amenities including Infinity pool and gym. Being hailed as the Downtown of Chesapeake, this apartment is a distinctive, urban mixed-use community singularly focused on quality amenities. If you're looking for a bustling community complete with luxurious surroundings and the most popular spots in Chesapeake, this is the place for you.
$53 per night
Private room in Norfolk
Southern Charm - Private Room & Bath by Downtown!
Live BIG by the City! This stately Colonial is 2 miles from Downtown Norfolk, with all the bells and whistles you’d expect from a modern home! This is the perfect stop-in for medical professionals, military service members, and all visitors to the Mermaid City. With this 2 bdrm space you get 4 queen size beds and the whole loft area approx. 1,100 sqft. to yourselves. Easy access to Shipyards, Military Bases, and Chesapeake. Only a 10 minute drive to EVMS, CHKD, and Naval Med. Center Portsmouth.
$50 per night
SUPERHOST
Private room in Chesapeake
⚓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.
$86 per night
SUPERHOST

Stay near Chesapeake's top sights

Photo of Veterans United Home Loans Amphitheater at Virginia Beach
Veterans United Home Loans Amphitheater at Virginia Beach56 locals recommend
Photo of Lynnhaven Mall
Lynnhaven Mall99 locals recommend
Photo of Mount Trashmore Park
Mount Trashmore Park83 locals recommend
Photo of Waterside District
Waterside District143 locals recommend
Photo of Greenbrier Mall
Greenbrier Mall25 locals recommend
Photo of Chrysler Museum of Art
Chrysler Museum of Art184 locals recommend

Weekly rentals in Chesapeake

Private room in Chesapeake
Silver Suite - Private Bedroom
$48 per night
SUPERHOST
Private room in Norfolk
Cozy Bedroom near Downtown Norfolk!
$60 per night
SUPERHOST
Private room in Chesapeake
Queen Bed w/ Private Bath & Private Entrance!
$62 per night
SUPERHOST
Private room in Chesapeake
A clean & spacious private room
$60 per night
Private room in Virginia Beach
Cozy Private Bedroom in a quiet neighborhood.
$65 per night
SUPERHOST
Private room in Norfolk
Incredible Room near Naval Bases, ODU, & EVMS
$47 per night
SUPERHOST
Private room in Norfolk
Waterside Oasis -Private King Suite W/Bathroom
$70 per night
SUPERHOST
Private room in Chesapeake
Full of natural light private bedroom
$59 per night
SUPERHOST
Private room in Chesapeake
Guestroom with Pull Out Bed
$41 per night
SUPERHOST
Guest suite in Chesapeake
King Guest Suite - A TOGAR Family Vacation Rental
$75 per night
SUPERHOST
Private room in Ocean View
Private Room close by Navy Base
$69 per night
Private room in Chesapeake
Private, Spacious Studio Apartment, Bath, Quiet
$63 per night
SUPERHOST

Stays in Downtown Norfolk

Private room in Ghent
The Owl Room in Late 1800s Historic House
$103 per night
SUPERHOST
Condo in Downtown Norfolk
Best Luxury Condo in Downtown Norfolk
$149 per night
SUPERHOST
Guesthouse in Downtown Norfolk
Private Guesthouse, Ghent/Downtown near ODU, EVMS
$120 per night
SUPERHOST
Rental unit in Ghent
The Rosalie Suite 3, Steps from Norfolks Hospitals
$115 per night
SUPERHOST

Stays in Ghent

Home in Ghent
Vintage Classic in West Ghent near ODU, EVMS, CHKD
$55 per night
Rental unit in Norfolk
Old Victoria in Norfolk
$50 per night
SUPERHOST
Rental unit in Ghent
The Rosalie Suite 2, Steps from Norfolks Hospitals
$116 per night
SUPERHOST
Rental unit in Ghent
Colley Manor - Cardinal Suite
$98 per night

Stays in Olde Towne

Rental unit in Olde Towne
Private 1 Bed Apt - Historic Olde Towne Portsmouth
$104 per night
SUPERHOST
Condo in Olde Towne
Historic Portsmouth “Captains Quarters”
$125 per night
SUPERHOST
Rental unit in Olde Towne
Charming cozy apt historic in Old Towne Portsmouth
$111 per night
SUPERHOST
Rental unit in Portsmouth
Downtown City View 1bdrm Luxury Apartment
$116 per night
SUPERHOST
  1. Airbnb
  2. United States
  3. Virginia
  4. Chesapeake