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Holiday rentals in Chesapeake

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Top-rated holiday rentals in Chesapeake

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

  1. Private room
  2. Chesapeake
Cozy and Sparkling Room in Chesapeake 2

Proximate to everything. Airport, Mall and shopping centers. Available self check-in. The home is located in a peaceful and welcoming environment. We love meeting new people.

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.

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.

Holiday rentals for every style

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Stay near Chesapeake's top sights

Photo of Mount Trashmore Park
Mount Trashmore Park42 locals recommend
Photo of Chrysler Museum of Art
Chrysler Museum of Art50 locals recommend
Photo of MacArthur Center
MacArthur Center51 locals recommend
Photo of Lynnhaven Mall
Lynnhaven Mall25 locals recommend
Photo of Nauticus
Nauticus70 locals recommend
Photo of Town Point Park
Town Point Park13 locals recommend

Other great holiday rentals in Chesapeake

  1. Private room
  2. Chesapeake
The train track heaven
  1. Private room
  2. Chesapeake
Cozy room in nice house close to downtow Norfolk
SUPERHOST
  1. Private room
  2. Virginia Beach
One bedroom in a single family house with home gym
  1. Private room
  2. Virginia Beach
Tropic Napper
SUPERHOST
  1. Entire guest suite
  2. Chesapeake
King Guest Suite - A TOGAR Family Vacation Rental
  1. Private room
  2. Norfolk
Peaceful Private Room centrally located in Norfolk
  1. Private room
  2. Chesapeake
Beautiful family's home close to downtown Norfolk
  1. Entire townhouse
  2. Chesapeake
The Arcade Theater 🍿🎬 (Discounts Available)
  1. Private room
  2. Virginia Beach
A Nice and Comfortable Room in Virginia Beach
  1. Entire bungalow
  2. Chesapeake
Private and Cozy Bungalow Loaded with Amenities
  1. Private room
  2. Norfolk
Lovely private room Navy Base/ ODU/Downtown
  1. Entire rental unit
  2. Norfolk
Old Victoria in Norfolk
  1. Airbnb
  2. United States
  3. Virginia
  4. Chesapeake