Holiday rentals in Chesapeake

Search and compare Chesapeake, VA holiday rentals from hundreds of travel sites on HotelsCombined and save.

...and more

Learn why travellers love HotelsCombined

Compare hotel ratings collected from thousands of user reviews.

One search gives you accurate pricing on affordable hotels.

Customie your results by hotel chain, amenities, price and more.

Search for hotels as many times as you want – for free.

Other accommodations in Chesapeake

Find the perfect holiday rental for your stay in Chesapeake. There are 99 hotels in Chesapeake and price data was last updated on 23 March 2026. The average price for a hotel in Chesapeake is .
Comfort Inn & Suites Chesapeake - Portsmouth
Comfort Inn & Suites Chesapeake - Portsmouth

Comfort Inn & Suites Chesapeake - Portsmouth

3355 South Military Highway, Chesapeake, VA, United States
4.7 km from city centre
Pool
Free Wi-Fi
Parking
$154
Avg. per night
View Deal
Wingate by Wyndham Chesapeake
Wingate by Wyndham Chesapeake

Wingate by Wyndham Chesapeake

817 Greenbrier Circle, Chesapeake, VA, United States
5.7 km from city centre
Pool
Free Wi-Fi
Parking
$151
Avg. per night
View Deal
Courtyard by Marriott Chesapeake Greenbrier
Courtyard by Marriott Chesapeake Greenbrier

Courtyard by Marriott Chesapeake Greenbrier

1562 Crossways Boulevard, Chesapeake, VA, United States
4.9 km from city centre
Free Wi-Fi
Parking
$182
Avg. per night
View Deal

Where to stay in Chesapeake

Explore different neighbourhoods and areas within Chesapeake to find the perfect location for your stay. Map data was last updated on 23 March 2026.
Utilise the map to find properties close to the Chesapeake area(s) or attractions you plan on visiting. Clicking on a holiday rental name will take you to a page with pricing, reviews, and more useful information.

Facts about staying in Chesapeake

Find useful tips and insights about staying in Chesapeake to help you make the most of your experience. FAQs were last updated on 23 March 2026.

  • How much does a holiday rental in Chesapeake cost?

    $205/night is a typical cost for a holiday rental in Chesapeake throughout the year. Rental prices do vary though, and you’ll find that November is the most expensive month to book, and March is the cheapest month to book. HotelsCombined users recently found Chesapeake holiday rentals for as low as $92/night. In general, any Chesapeake rental for $194 or less is a good deal.

  • Are there any Motel holiday rentals in Chesapeake?

    At the moment, there are 3 properties listed as a Motel holiday rental in Chesapeake. A popular Motel in Chesapeake amongst our users is Bowers Hill Inn.

Find better results for your stay in Chesapeake