Chesapeake, VA, USA

Chesapeake, VA, USA

We found 1,150 holiday rentals — enter your dates for availability


Find the best place to stay — Chesapeake

Where to stay around Chesapeake?

Our 2018 accommodation listings offer a large selection of 1,150 holiday lettings near Chesapeake. From 492 houses to 361 condos, find unique self catering accommodation for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay near Chesapeake is on HomeAway.

What is the best area to stay when travelling to Chesapeake?

Whether you are travelling solo or with family and friends, here are the areas with the largest selection of holiday accommodations for a long holiday or just a weekend break in Chesapeake:

  • Sandbridge Beach: 478 holiday homes
  • Ocean View: 65 holiday homes
  • Buckroe Beach: 18 holiday homes
  • Willoughby Spit: 47 holiday homes
  • Northeast Virginia Beach: 540 holiday homes

For other neighbourhoods, please use our search bar to access the selection of holiday rentals available.

What are the most popular points of interest and landmarks to stay near when travelling to Chesapeake?

HomeAway offers a large selection of holiday accommodations near great places in Chesapeake. From HomeAway travellers, the most popular points of interest to stay near are:

  • Virginia Beach National Golf Club: 1,150 holiday lettings
  • Chesapeake Golf Club: 350 holiday lettings
  • Chesapeake Veterans' Memorial: 1,110 holiday lettings
  • Cahoon Plantation Golf Course: 206 holiday lettings
  • Chesapeake City Hall: 1,113 holiday lettings

But there are many other points of interest around Chesapeake listed on HomeAway where you can find your place to stay. Please use our search bar to access the selection of holiday rentals available near the point of interest of your choice.

Can I rent houses in Chesapeake?

Yes, of course. HomeAway offers 492 houses in Chesapeake. Our other popular types of Chesapeake holiday rentals include:

  • Condos: 361 self catering accommodations
  • Apartments: 60 self catering accommodations
  • Cottages: 56 self catering accommodations

But you can also enjoy a great stay in one of our other holiday rentals including bungalows and more.

Can I find a holiday accommodation with pool in Chesapeake?

Yes, you can select your preferred holiday accommodation with pool among our 588 holiday homes with pool available in Chesapeake. Please use our search bar to access the selection of holiday rentals available.

    Delight in the beach landscape of Chesapeake

    Enjoy the area's live music, theatre and sports with a rental holiday home in Chesapeake. Travellers especially like the shopping, restaurants and beaches in this romantic and family-friendly city. Top attractions in the area include Children's Museum of Virginia, Nauticus National Maritime Center and Moses Myers House. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

    Attractions in and around Chesapeake

    First time in Chesapeake and looking for things to do? Some of the area's family-friendly attractions for travellers include Ocean Breeze Waterpark, Virginia Aquarium and Marine Science Center and Virginia Zoo. Visitors searching for nearby cultural experiences can take a trip to Moses Myers House and Lynnhaven House, or spend an enlightening afternoon at Children's Museum of Virginia or Nauticus National Maritime Center. To appreciate the outdoor scene, make time for beaches such as Chesapeake Beach and Croatan Beach, and green spaces such as Norfolk Botanical Garden and First Landing State Park. You could easily spend a day shopping at Greenbrier Mall and Chesapeake Square Mall. To discover the region's top popular attractions, head to Chrysler Museum of Art, Virginia Air and Space Center and Cape Henry Lighthouse during your stay. Other places to visit in town include Oak Grove Lake Park, Cahoon Plantation Golf Course and Chesapeake Arboretum.