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Holiday rentals in Chesapeake

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chesapeake

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

Spacious  In Law Master Suite
SUPERHOST
Private room · 2 guests · 1 bed · 1 private bathroom

Spacious In Law Master SuiteBeautiful private in law suite with private bathroom in the suburbs of Chesapeake close to the interstate, military bases, restaurants & malls. Short drive to Virginia Beach.

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

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.

Sweet Suite!
SUPERHOST
Entire guest suite · 4 guests · 4 beds · 1.5 bathrooms

Sweet Suite!Private attached MOTHER IN LAW suite (not the whole house) in an quiet neighborhood in the heart of Hampton Roads. We offer keyless entry and a private parking space, private pool and backyard grill area. All are welcome here, including pets. We ask that you tell us if you are bringing a pet(s) and I'll message you about the added pet fee. We are minutes away from all major attractions and less than 5 minutes from major highways. Our location gives you easy access to the Outer Banks.

Holiday rentals for every style

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Popular amenities for Chesapeake holiday rentals

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

Other great holiday rentals in Chesapeake

  1. Entire apartment
  2. Norfolk
Hometel La'Flaire
SUPERHOST
  1. Entire guest suite
  2. Norfolk
American Haven:UniqueProperty;Spa- Fitness-Kitchen
SUPERHOST
  1. Private room
  2. Norfolk
Charming Bedroom in Historic House!
  1. Entire residential home
  2. Portsmouth
Homey 1st Floor Apartment in Parkview
  1. Entire residential home
  2. Portsmouth
COZY MODERN HOME IN HISTORIC PORT NORFOLK
SUPERHOST
  1. Entire guest suite
  2. Virginia Beach
*NEW* Virginia Beach Studio
SUPERHOST
  1. Entire guest suite
  2. Chesapeake
King Guest Suite - A TOGAR Family Vacation Rental
SUPERHOST
  1. Entire guest suite
  2. Virginia Beach
Guest suite with kitchenette, Private bath/entry.
SUPERHOST
  1. Entire guest house
  2. Norfolk
Private Guesthouse, Ghent/Downtown near ODU, EVMS
  1. Entire townhouse
  2. Virginia Beach
3 bedroom, 3.5 bath townhouse 8mi to oceanfront .
SUPERHOST
  1. Entire rental unit
  2. Portsmouth
An Apt. in the heart of Historic Portsmouth Unit 1
SUPERHOST
  1. Entire residential home
  2. Portsmouth
Brick Bungalow in historic Port Norfolk

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