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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
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.
$89 per night
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!
$66 per night
Superhost
Guesthouse 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.
$79 per night

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 vacation rentals in Chesapeake

Superhost
Guest suite in Virginia Beach
Spirit Bear Lake! Spacious, peaceful, and private
$107 per night
Superhost
Condo in Virginia Beach
2 Bedroom Condo ONE Block from the Oceanfront
$62 per night
Superhost
Apartment in Virginia Beach
3 Blocks 2 Beach! A ViBe District Beach Retreat!
$79 per night
Superhost
Guest suite in Norfolk
Beachfront Exclusive Bay front Suite
$134 per night
Superhost
Condo in Virginia Beach
2 bedroom condo with oceanfront one block away!
$83 per night
Superhost
Guest suite in Virginia Beach
Guest Suite Studio w/ Kitchenette & Private bath.
$65 per night
Superhost
Condo in Norfolk
Modern And Cozy!
$159 per night
Superhost
Barn in Virginia Beach
Cozy craftsman barn near the bay!
$106 per night
Superhost
Guesthouse in Norfolk
Private Guesthouse, Ghent/Downtown near ODU, EVMS
$119 per night
Superhost
Apartment in Virginia Beach
5 Minute Walk to the Beach!
$70 per night
Superhost
Home in Chesapeake
The Full House
$110 per night
Superhost
Townhouse in Chesapeake
2BR-1.5 Bath Electric & Vibrant R&R Townhome
$108 per night

Frequently Asked Questions

  • Where should I stay in Chesapeake?

    Make yourself at home in Chesapeake by choosing from our most frequently booked neighborhoods. We have over 110 vacation rentals in Salem, over 560 vacation rentals in Olde Towne, over 290 vacation rentals in Ghent, and over 560 vacation rentals in Downtown Norfolk.

  • Are there vacation rentals with a dedicated workspace in Chesapeake?

    Yes! Work meets play with ease at over 580 vacation rentals in Chesapeake featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Chesapeake?

    Four-legged friends are welcome in Chesapeake. Choose from more than 320 vacation rentals for guests traveling with pets.

  • Are there Chesapeake vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 140 vacation homes with pools in Chesapeake, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in rv rentals in Chesapeake?

    Experience the best of Chesapeake with our rv rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Chesapeake have a bbq area?

    Absolutely! We offer over 140 house rentals with a bbq area in Chesapeake. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Chesapeake have a gym?

    Absolutely! We offer over 50 apartment rentals with a gym in Chesapeake. Enjoy a tailored experience with all the comforts you desire.

  • Do private suite rentals in Chesapeake have wifi?

    Absolutely! We offer over 40 private suite rentals with wifi in Chesapeake. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Chesapeake have self check-in?

    Absolutely! We offer over 190 house rentals with self check-in in Chesapeake. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly apartment rentals in Chesapeake?

    Chesapeake has more than 60 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Destinations to explore

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