A golf course, a large building complex, and a marina by a river.

Chesapeake Holiday Rentals

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Chesapeake holiday rentals

Terrace/patio

1. stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
3.5 star property
Suffolk
9.6 out of 10, Exceptional, (97 reviews)
"Perfect! Will stay again and will look for this brand in my future travels."
United States
Melissa
The price is S$175
includes taxes & fees
1 Sept - 2 Sept
stayAPT Suites Suffolk-Chesapeake
Property grounds

2. stayAPT Suites Hampton

stayAPT Suites Hampton
2.5 star property
Coliseum Central
The price is S$178
includes taxes & fees
19 Aug - 20 Aug
stayAPT Suites Hampton
Interior

3. Centrally Located Hampton Roads Home w/ Game Room!

Centrally Located Hampton Roads Home w/ Game Room!
3.0 star property
Portsmouth
The price is S$900
includes taxes & fees
4 Sept - 5 Sept
Centrally Located Hampton Roads Home w/ Game Room!
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

Hampton Inn Virginia Beach-Oceanfront South

Hampton Inn Virginia Beach-Oceanfront South

10/10 Excellent
"Yes"
Robert 3-night trip
Posted 2 hours ago
Hampton Inn Virginia Beach-Oceanfront South

Frequently asked questions

Are there holiday rentals in Chesapeake?

Yes, there are holiday rentals in Chesapeake close to Parkview Play Area, 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 39 holiday rentals for your stay in Chesapeake.

What’s there to see and do in Chesapeake?

Family-friendly attractions include Parkview Play Area and Broadmoor Play Area, whereas Chesapeake City Park and Oak Grove Lake Park are a couple of great spots to enjoy the outdoors. While in the area, you can also visit popular places such as Sandbridge Beach and Veterans United Home Loans Amphitheater at Virginia Beach.

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.