Skip to content
Sign up
Log in
Vacation rentals in Chesapeake Beach

Vacation rentals in Chesapeake Beach

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chesapeake Beach

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

  • Virginia Beach 2 King BR apt 100 feet from beach
    SUPERHOSTEntire guest suite · 7 guests · 4 beds · 1 bathroom
    Virginia Beach 2 King BR apt 100 feet from beach

    2 King Bedroom apartment 100 feet from the beach. Private and secluded. Private entrance to In-law suite separated from the main house. Watch the sunset while sitting on the beach and pet friendly.

    What guests are saying:

    “Awesome location with private beach access. Beach was great - wide, clean, dog-friendly! The guest suite was larger than I expected, is very private with bright, airy, open rooms. The mattresses were very comfortable - I even looked to see what they were!! Hardwood floors and Roomba made sandy feet a breeze! The neighborhood is quiet and residential, great restaurants very close by with easy access to VA Beach. Traci and Kurt were lovely to work with and very responsive. It was the perfect place for a beach getaway with my pup!”

  • Chicks Beachfront
    SUPERHOSTEntire house · 4 guests · 2 beds · 2.5 bathrooms
    Chicks Beachfront

    Lovely beach front house in the heart of Chick's Beach. Wake up to idyllic views of the ocean every morning! Within walking distance from several local venues for authentic seafood, live music, and craft breweries.

    What guests are saying:

    “My family and I stayed at Jeremy’s place for Memorial Day weekend. We were unsure of how COVID would affect our activities, so we wanted a place right on the water, just incase we weren’t able to use the beaches. This location could NOT have been better!! It was very close to some of our favorite restaurants and beachFRONT, exactly as described (the deck views were BEYOND relaxing in the morning!!). We were able to cook lunches and dinner with the kitchen supplies available (kitchen supplies weren’t abundant, but we were definitely able to make-do), and found the washer and dryer to be very convenient! We unintentionally arrived a bit early and had a chance to meet the cleaning staff.. she was an absolute doll and did a thorough job cleaning the home.. we felt very safe as far as cleanliness and COVID guidelines were concerned. We did have our dog with us, and the space worked out well for her as well (all surrounding neighbors also have dogs- but they were never a disturbance). The only negatives I could possibly report would be that my 65 year old father found his bed to be very uncomfortable (my 35 year old husband and I noticed no such issues), and parking with our two cars was a bit inconvenient, especially as the beaches filled up (this was something the host made us aware of in advance, though!). There is definitely only room for one mid-sized car at a time. All-in-all it was a great trip and a wonderful place to stay. There were plenty of amenities (ie: beach chairs, beach umbrella, wine opener, washer/dryer, beach towels, dish washer and detergent, Keurig cups, coffee maker, etc) and the location absolutely cannot be beat! I would definitely recommend a relaxing stay at this location!”

  • Play by the Bay.....swim, boat, fish and much more
    SUPERHOSTEntire house · 7 guests · 4 beds · 2 bathrooms
    Play by the Bay.....swim, boat, fish and much more

    Fantastic beach home with three bedrooms and two baths. Great views of the Chesapeake Bay from the Living room and deck. Just steps away from the beach access. Updated with high end appliances. First floor has Living room-dining room combo with vaulted ceilings, kitchen, guest bedroom and bathroom. Second floor has two bedrooms and a bath. There is TV in three rooms, Wi-Fi, large deck with natural gas Weber grill. Washer-dryer. Two parking spaces in driveway plus on street parking.

    What guests are saying:

    “My partner and our two kids (7 and 11) rented this airbnb for a VA Beach weekend stay. It was the absolute perfect space for my family. The use of space in the home and the way that it is decorated and organized is so smart. It was immaculately clean and had everything we could possibly need and the beach is just steps away! The owners of the home were so easy to communicate with but also very respectful of our space and privacy. My whole family had such a nice time, my kids didn't want to leave! I would 100% recommend this rental and can honestly say it is hands down one of the best airbnb experiences I have had. Thank you so much Diana and Thomas!”

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Chesapeake Beach holiday rentals

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

Other great holiday rentals in Chesapeake Beach

Chic’s Beach Beauty
SUPERHOSTEntire house
Chic’s Beach Beauty
Price:€119 / night
Ocean Park Cottage - Garden by Bay
SUPERHOSTEntire cottage
Ocean Park Cottage - Garden by Bay
Price:€60 / night
Zen East
SUPERHOSTEntire house
Zen East
Price:€128 / night
Beach Livin' by the Chesapeake Bay - VA Beach
SUPERHOSTEntire townhouse
Beach Livin' by the Chesapeake Bay - VA Beach
Price:€202 / night
Chic's Beach (is Open!) Rental and Fishing
SUPERHOSTEntire house
Chic's Beach (is Open!) Rental and Fishing
Price:€258 / night
Beach Front Cottage
Entire cottage
Beach Front Cottage
Price:€169 / night
Beach View on Chic's Beach- Sleeps 12! W/D & WIFI!
SUPERHOSTEntire house
Beach View on Chic's Beach- Sleeps 12! W/D & WIFI!
Price:€274 / night
Chic's Beach Living
Entire flat
Chic's Beach Living
Price:€310 / night
Virginia Beach waterfront home away from home!
SUPERHOSTEntire guest suite
Virginia Beach waterfront home away from home!
Price:€128 / night
Impressive Bay front Condo with a View
SUPERHOSTEntire house
Impressive Bay front Condo with a View
Price:€335 / night
Modern 4bdr Oceanfront home
SUPERHOSTEntire house
Modern 4bdr Oceanfront home
Price:€598 / night
Enjoy your little slice of heaven in Chics Beach!
SUPERHOSTEntire guest suite
Enjoy your little slice of heaven in Chics Beach!
Price:€71 / night
Show all