Colorful sunset over riverside resort in Cambridge Maryland USA

Chesapeake Holiday Rentals

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sept - 13 Sept
In four months
9 Oct - 11 Oct

Our top choices for Chesapeake holiday rentals

Living area

Nyakio Suite

Nyakio Suite
2.0 star property
Greenbrier
The price is S$1,109
includes taxes & fees
24 Jun - 25 Jun
Nyakio Suite
2 bedrooms

The Speakeasy Downtown Newport News

The Speakeasy Downtown Newport News
2.0 star property
Downtown Newport News
The price is S$419
includes taxes & fees
22 Jun - 23 Jun
The Speakeasy Downtown Newport News
Terrace/patio

stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
3.5 star property
Suffolk
9.4 out of 10, Exceptional, (83 reviews)
"Very clean and modern room at a very reasonable price. We will definitely stay there again if we are in that area."
United States
Scott
The price is S$176
includes taxes & fees
29 Jun - 30 Jun
stayAPT Suites Suffolk-Chesapeake
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

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

8/10 Good
"It was alright"
james 3-night trip
Posted 1 hour ago
Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

Frequently asked questions

Are there holiday rentals in Chesapeake?

Yes, there are holiday rentals in Chesapeake close to Riverwalk Parkway Park and Playground, 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 40 holiday rentals for your stay in Chesapeake.

What’s there to see and do in Chesapeake?

Family-friendly attractions include Riverwalk Parkway Park and Playground and Broadmoor Play Area, whereas Chesapeake City Park and Dismal Swamp Canal 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 Naval Station Norfolk.

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.