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Vacation rentals in Chesapeake

Vacation 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.

  • The Suite at Lynnhaven
    SUPERHOSTEntire guest house · 4 guests · 1 bed · 1 bathroom
    The Suite at Lynnhaven

    Welcome to the Suite! This is a 1 bed/1 bath living area with comfortable sleeping arrangement for 4 - queen bed and queen sofa bed. Full kitchen with cookware needed to prepare your own meals. Streaming TV available to go along with very fast wifi.

    What guests are saying:

    “This space is a gem. It's convenient, pet friendly, new, and super clean. Parking was better than expected, especially traveling with a car load and pupper. An easy drive to the beach and sites, and easy accessibility to the highway if passing through. Perfect open concept for what we were looking for, room for a cot or air mattress if need extra sleeping space; full kitchen, and a great patio area for unwinding. Would stay again if passing through this area!!”

  • Beautiful and Chic, One Room Studio Apartment
    SUPERHOSTEntire guest house · 2 guests · 1 bed · 1 bathroom
    Beautiful and Chic, One Room Studio Apartment

    Chic one-room 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.

    What guests are saying:

    “Seriously everything about this air bnb Is outstanding! I arrived and was greeted with a personalized note wishing me a enjoyable stay back home including a basket full of snacks next to it. The bathroom was fully stocked with everything you might need to get ready in the morning, I felt like I didn't need to bring anything extra except for maybe my make up and curling iron. The location was also absolutely perfect. I was 10 to 15 minutes within everything that I wanted to see. The value of this stay is incredible… Highly recommend staying here instead of giving your money to a hotel. Next time I come home to Virginia I will undoubtably stay here again! The hosts are extremely responsive, and kind!”

  • Chesapeake 2-Bedroom Guest House
    SUPERHOSTEntire guest house · 6 guests · 2 beds · 1.5 bathrooms
    Chesapeake 2-Bedroom Guest House

    Quiet country setting in Chesapeake, VA. Paved parking for 2 vehicles. Breakfast - cereal, milk, coffee. 1 hour to Colonial Williamsburg. 1/2 hour to the beaches. 20 minutes to shopping malls. 5 minutes to grocery store. Excellent neighborhood to jog, walk or run. The apartment is upstairs over a 3-car detached garage. No pets. Beach towels provided in addition to bed linens and bath towels. LOCALS MUST SEND INQUIRY BEFORE BOOKING. ANY NON-PAYING LOCAL GUESTS MUST BE PRE-APPROVED.

    What guests are saying:

    “Mrs. Nina is an awesome host. She greeted us when we arrived . The accommodations were perfect for my family and everything we needed seemed to be available at our fingertips. She made herself available while at the same time gave us space. Very welcoming and felt the southern hospitality. Definitely recommend this place and also very close to restaurants and grocery shopping. Justin”

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Chesapeake holiday rentals

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

Other great holiday rentals in Chesapeake

4 BR Ranch W/ Pool and Hot Tub
SUPERHOSTEntire house
4 BR Ranch W/ Pool and Hot Tub
Price:€203 / night
River House Private Studio Apt-Poolside
SUPERHOSTPrivate room
River House Private Studio Apt-Poolside
Price:€155 / night
Sweet Suite!
SUPERHOSTEntire guest suite
Sweet Suite!
Price:€75 / night
Charming Apartment in Historic Neighborhood
SUPERHOSTEntire flat
Charming Apartment in Historic Neighborhood
Price:€54 / night
Private Victorian Carriage House
SUPERHOSTEntire guest house
Private Victorian Carriage House
Price:€44 / night
Waterfront Oasis
Entire cottage
Waterfront Oasis
Price:€146 / night
Zen Guest Room with Private Bath
SUPERHOSTPrivate room
Zen Guest Room with Private Bath
Price:€33 / night
Quiet neighborhood 7 miles from the Beaches
SUPERHOSTEntire guest suite
Quiet neighborhood 7 miles from the Beaches
Price:€69 / night
Clean Modern Retreat. New.
SUPERHOSTEntire guest suite
Clean Modern Retreat. New.
Price:€132 / night
Cozy Room in Quiet Neighborhood Bedroom A
SUPERHOSTPrivate room
Cozy Room in Quiet Neighborhood Bedroom A
Price:€32 / night
King Guest Suite - A TOGAR Vacation Rental
SUPERHOSTEntire guest suite
King Guest Suite - A TOGAR Vacation Rental
Price:€58 / night
Cozy, Private 1st Floor Apartment in Historic Home
SUPERHOSTEntire flat
Cozy, Private 1st Floor Apartment in Historic Home
Price:€71 / night
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