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Holiday rentals in Chesapeake

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Travel insights for holiday rentals in Chesapeake

Use these up-to-date, data-driven insights about booking a holiday rental in Chesapeake including ideal times to book, pricing trends, and more.

What is the cheapest day to stay in a vacation rental in Chesapeake?

The cheapest day to stay in Chesapeake is Sunday ($536). On the other hand, travelers can expect to pay the most on Tuesday, when the average nightly price is $2,080.
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Other accommodations in Chesapeake

Find the perfect holiday rental for your stay in Chesapeake. There are 107 hotels in Chesapeake and price data was last updated on 18 September 2025. The average price for a hotel in Chesapeake is .
Bowers Hill Inn
Bowers Hill Inn

Bowers Hill Inn

4725 West Military Highway, Chesapeake, VA, United States
12.0 km from city centre
Free Wi-Fi
Parking
Air conditioning
$117
Avg. per night
View Deal
Red Roof Inn Chesapeake Conference Center
Red Roof Inn Chesapeake Conference Center

Red Roof Inn Chesapeake Conference Center

724 Woodlake Drive, Chesapeake, VA, United States
5.4 km from city centre
Free Wi-Fi
Air conditioning
$134
Avg. per night
View Deal
Quality Inn Chesapeake
Quality Inn Chesapeake

Quality Inn Chesapeake

100 Red Cedar Court, Chesapeake, VA, United States
3.1 km from city centre
Free Wi-Fi
Parking
$114
Avg. per night
View Deal
SpringHill Suites by Marriott Chesapeake Greenbrier
SpringHill Suites by Marriott Chesapeake Greenbrier

SpringHill Suites by Marriott Chesapeake Greenbrier

1446 Crossways Boulevard, Chesapeake, VA, United States
3.8 km from city centre
Pool
Free Wi-Fi
Airport shuttle
$206
Avg. per night
View Deal
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
$127
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 18 September 2025.
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 18 September 2025.

  • How much does a holiday rental in Chesapeake cost?

    $379/night is a typical cost for a holiday rental in Chesapeake throughout the year. Rental prices do vary though, and you’ll find that August 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 $45/night. In general, any Chesapeake rental for $297 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

Consider other places to stay in Chesapeake

Stay at one of these places that users have found on HotelsCombined.
Chesapeake Bed & Breakfasts
Chesapeake Inns
Chesapeake Motels
Chesapeake Resorts

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