Photo by Kaylee Spinhirn

Chesapeake Holiday Rentals

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Check prices for these dates

Tonight
16 Dec - 17 Dec
Tomorrow
17 Dec - 18 Dec
This weekend
19 Dec - 21 Dec
Next weekend
26 Dec - 28 Dec

Our top choices for Chesapeake holiday rentals

Property grounds
Mariners Cove 4 Bedroom Cottage by RedAwning

Cottage in Willoughby Spit

Mariners Cove 4 Bedroom Cottage by RedAwning
3.0 star property
8.0 out of 10, Very good, (1)
"Great location right on the water with lots of space inside and out. The host was very helpful and easy to work with. "
United States
Arvind
The price is S$576
includes taxes & fees
21 Dec - 22 Dec
Mariners Cove 4 Bedroom Cottage by RedAwning
2 bedrooms
The Speakeasy Downtown Newport News

Apartment in Downtown Newport News

The Speakeasy Downtown Newport News
2.0 star property
The Speakeasy Downtown Newport News
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chesapeake Hotel Reviews

Hyatt Place Virginia Beach / Oceanfront

Hyatt Place Virginia Beach / Oceanfront

10/10 Excellent
"Awesome "
Mike 2-night trip
Posted 2 days ago
Hyatt Place Virginia Beach / Oceanfront

Frequently asked questions

Are there holiday rentals in Chesapeake?

Yes, there are holiday rentals in Chesapeake close to Chesapeake Arboretum, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the array of shops and popular beaches in Chesapeake. While you're in the area, you can also enjoy the top-notch restaurants and live music.

How many holiday rentals are there in Chesapeake?

Expedia has 38 holiday rentals for your stay in Chesapeake.

What’s there to see and do in Chesapeake?

Family-friendly attractions include Broadmoor Play Area and Parkview Play Area, whereas Oak Grove Lake Park and Chesapeake Arboretum are a couple of great spots to enjoy the outdoors. Greenbrier Mall and Chesapeake Conference Center are other places to visit while you're in town.

What’s a holiday rental in Chesapeake like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chesapeake. Holiday rentals feature extras such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from shared hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for small groups.