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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.

Superhost
Guest suite in Chesapeake
Sweet Suite!
Private attached MOTHER IN LAW suite (not the whole house) in a 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.
Individual Host
Superhost
Guest suite in Chesapeake
King Guest Suite - A TOGAR Family Vacation Rental
Come enjoy a great stay in this beautiful private In-law suite, located in the heart of Chesapeake where you can get lost in nature, peruse the fare at a farmer's market, or picnic on the water's edge with your family. Just within 15 to 30 minutes from surrounding Naval bases, Virginia Beach Oceanfront and Downtown Norfolk. All you have to do us gas-up and unplug. We'll take it from there. Reserve your stay today and let your moments begin!
Individual Host
Superhost
Guest house in Chesapeake
Beautiful and Chic, One Room Studio Apartment
Chic private apartment is located in a quiet neighborhood at the end of the peninsula were the Indian River flows into the Elizabeth River. Centrally located, we are nestled in the heart of Hampton roads with Virginia Beach 1 mile to the east and Norfolk 1 mile to the north. Twenty minutes from everywhere you'll want to go: the airport, the beach, multiple shopping centers and several universities.
Individual Host

Stay near Chesapeake's top sights

Lynnhaven Mall99 locals recommend
Veterans United Home Loans Amphitheater at Virginia Beach56 locals recommend
Waterside District143 locals recommend
Mount Trashmore Park83 locals recommend
MacArthur Center154 locals recommend
Town Point Park32 locals recommend

Other great holiday rentals in Chesapeake

Superhost
Guest suite in Virginia Beach
Spirit Bear Lake! Spacious, peaceful, and private
Professional Host
Superhost
Apartment in Virginia Beach
2 Bedroom Condo ONE Block from the Oceanfront
Superhost
Flat in Virginia Beach
3 Blocks 2 Beach! A ViBe District Beach Retreat!
Individual Host
Superhost
Guest suite in Norfolk
Beachfront Exclusive Bay front Suite
Individual Host
Superhost
Apartment in Virginia Beach
2 bedroom condo with oceanfront one block away!
Individual Host
Superhost
Guest suite in Virginia Beach
Small/ cozy guest suite w/ private bath & jet-tub
Individual Host
Superhost
Apartment in Norfolk
Modern And Cozy!
Individual Host
Superhost
Barn in Virginia Beach
Cozy craftsman barn near the bay!
Professional Host
Superhost
Guest house in Norfolk
Private Guesthouse, Ghent/Downtown near ODU, EVMS
Individual Host
Superhost
Guest suite in Chesapeake
Purple Room- Rare Luxury Ste w/prkg - 1 of a kind!
Individual Host
Superhost
Flat in Virginia Beach
VB Oceanfront Studio Balcony,Beach,Boardwalk, Pool
Superhost
Flat in Virginia Beach
5 Minute Walk to the Beach!
Individual Host

Destinations to explore

  1. Airbnb
  2. United States
  3. Virginia
  4. Chesapeake