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Holiday hires 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 ($442). On the other hand, travelers can expect to pay the most on Tuesday, when the average nightly price is $1,714.
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Cheapest holiday rentals in Chesapeake, Virginia

Discover affordable stays in Chesapeake that provide a quality experience without breaking the bank. Hotels in Chesapeake can be found for as low as $123 per night. There is currently one property in Chesapeake that can be booked for this price. Econo Lodge Little Creek is one of the hotels that can be booked for the lowest price in Chesapeake. Price data was last updated on 9 September 2025
These are the lowest prices we've found on holiday rentals in Chesapeake at the moment. If you have flexibility with arrival and departure, use the search form to compare prices for other dates.
Econo Lodge Little Creek
Econo Lodge Little Creek

Econo Lodge Little Creek

Norfolk, VA, United States
11.7 km from city centre
Air conditioning
$123
Avg. per night
View Deal

Other accommodations in Chesapeake

Find the perfect holiday rental for your stay in Chesapeake. There are 108 hotels in Chesapeake and price data was last updated on 9 September 2025. The average price for a hotel in Chesapeake is .
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
$131
Avg. per night
View Deal
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
$106
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
$101
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
$188
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
$133
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 9 September 2025.
Whether you're visiting Chesapeake for leisure or business, utilise the map to find holiday rentals close to your ideal location. Users can click on a holiday rental's name to find more information about it, such as price, reviews, and amenities, and also find different deals for the property.

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 9 September 2025.

  • How much does a holiday rental in Chesapeake cost?

    $363 per night is how much a holiday rental in Chesapeake costs, on average. $41 per night was the cheapest price recently found by our users, though anything for $279 per night or less is a good deal. Keep in mind that Chesapeake holiday rental prices fluctuate throughout the year: the most expensive month to book is August, and the cheapest time to book is February.

  • What is the best Chesapeake holiday rental?

    The best holiday rental in Chesapeake is Econo Lodge Little Creek, according to our user data. 473 users from HotelsCombined gave the Econo Lodge Little Creek a 6.9/10 rating.

  • What’s the closest holiday rental to Norfolk Airport?

    If you’re looking to stay close to Norfolk Airport for your trip to Chesapeake, then consider booking a Econo Lodge Little Creek holiday rental. This holiday apartment is just 2.9 km away from the Chesapeake airport.

  • Are there any Motel holiday rentals in Chesapeake?

    If you’re looking to book a Motel holiday rental in Chesapeake, then you have 3 to choose from. We recommend looking at Bowers Hill Inn as it’s currently the most popular Motel rental among our users.

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Find better results for your stay in Chesapeake

Search cheap hotels with HotelsCombined. Use the hotel finder to search for the cheapest hotel deal for all major destinations around the world. HotelsCombined searches hundreds of hotel booking sites to help you find hotels and book the ones that suit you best. Since HotelsCombined searches many hotel sites at once, you can find discounted hotels quickly, including Hotels Under $76 and Hotels Under $152. Discover hotel discounts now and make your hotel reservation today.