Destination guide

Why people love visiting lively Chesapeake

The area's live music and theatre scene are just some of the reasons to come on holiday to Chesapeake. This romantic city is known for its shopping, restaurants and beaches. Children's Museum of Virginia and Nauticus National Maritime Center are just a couple of the must-see attractions in the area. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.


Sightseeing in and around Chesapeake

Are you hoping to discover attractions to visit while you're in town? Venture out of your holiday home and experience everything that makes Chesapeake a fun spot to go on holiday. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Ocean Breeze Waterpark (16.8 mi / 27 km)
  • Virginia Aquarium and Marine Science Center (17.2 mi / 27.7 km)
  • Virginia Living Museum (23.4 mi / 37.6 km)
  • Cahoon Plantation Golf Course (3 mi / 4.8 km)
  • Chesapeake Golf Club (3.8 mi / 6.1 km)
  • Virginia Zoo (7.5 mi / 12 km)

Seasonal weather averages in Chesapeake

If warm-weather activities are high on your list, July, August, June and September are the hottest months to visit, when temperatures average 30°F.

Natural features

Exploring the beaches and other natural features in Chesapeake

Whether you're an active traveller or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Chesapeake. Here are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Norfolk Botanical Garden (10.7 mi / 17.2 km)
  • First Landing State Park (17.9 mi / 28.8 km)
  • Oak Grove Lake Park (1.7 mi / 2.7 km)
  • Chesapeake Arboretum (3.2 mi / 5.1 km)
  • Chesapeake City Park (3.5 mi / 5.6 km)
  • Town Point Park (5.4 mi / 8.7 km)
How to get there

Travelling to and around Chesapeake

The nearest airport is in Norfolk, VA (ORF-Norfolk Intl.), located 10.1 mi (16.3 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Newport News, VA (PHF-Newport News - Williamsburg Intl.), which is 27.6 mi (44.5 km) away.

How many holiday rentals are available around Chesapeake?

Our 2020 accommodation listings offer a large selection of 2,742 holiday lettings around Chesapeake. From 1,711 houses to 526 flats & apartments, find unique self catering accommodation for you to enjoy a memorable stay with your family and friends for a long holiday or a weekend break.

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:

  • Greenbrier East: 39 holiday homes
  • Willoughby Spit: 195 holiday homes
  • Cottage Line: 68 holiday homes
  • Northeast Virginia Beach: 624 holiday homes
  • Bayview: 68 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? offers a large selection of holiday accommodations near great places in Chesapeake. From travellers, the most popular points of interest to stay near are:

  • Chesapeake Veterans' Memorial: 1,210 holiday lettings
  • Chesapeake City Park: 1,249 holiday lettings
  • Chesapeake Arboretum: 1,247 holiday lettings
  • Chesapeake Golf Club: 540 holiday lettings
  • Chesapeake City Hall: 1,212 holiday lettings

But there are many other points of interest around Chesapeake listed on 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. offers 1,711 Houses in Chesapeake. Our other popular types of Chesapeake holiday rentals include:

  • Flats: 526 self catering accommodations
  • Cottages: 125 self catering accommodations
  • Cabins: 125 self catering accommodations

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

Can I find a holiday accommodation with pool in Chesapeake?

Yes, you can select your preferred holiday accommodation with pool among our 1,673 holiday homes with pool available in Chesapeake. Please use our search bar to access the selection of holiday rentals available.

    Explore destinations around Chesapeake

    Virginia Beach
    1,378 holiday rentals
    843 holiday rentals
    2,084 holiday rentals
    595 holiday rentals
    1,836 holiday rentals
    187 holiday rentals
    81 holiday rentals
    Newport News
    938 holiday rentals
    173 holiday rentals
    Cape Charles
    176 holiday rentals
    584 holiday rentals
    1,842 holiday rentals
    23 holiday rentals
    1,443 holiday rentals
    882 holiday rentals
    16 holiday rentals
    36 holiday rentals
    Knotts Island
    115 holiday rentals
    Taylorwood Estates
    31 holiday rentals
    Cottage Park
    320 holiday rentals