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Check prices for these dates

In two weeks
8 May - 10 May
In two months
19 Jun - 21 Jun
In three months
17 Jul - 19 Jul
In four months
14 Aug - 16 Aug

Our top choices for Chesapeake holiday rentals

Indoor pool

The Ocean Key Virginia Beach Resort

The Ocean Key Virginia Beach Resort
3.0 star property
Northeast Virginia Beach
7.8 out of 10, Good, (1,499 reviews)
"Very easy check in, pool was nice and convenient for kids, great location to beach"
United States
Porsch
The price is ₹7,247
₹13,875 total
includes taxes & fees
11 May - 12 May
The Ocean Key Virginia Beach Resort
Terrace/patio

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
4.0 star property
Northeast Virginia Beach
8.2 out of 10, Very good, (1,248 reviews)
"Great location. Staff was friendly. Room was clean and cute with spacious bathroom and nice size kitchenette. "
United States
Jennifer
The price is ₹10,843
₹17,998 total
includes taxes & fees
6 May - 7 May
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
Terrace/patio

stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
2.5 star property
Suffolk
9.4 out of 10, Exceptional, (70 reviews)
"perfect stay. would definitely stay again "
United States
berry
The price is ₹11,082
₹12,726 total
includes taxes & fees
4 May - 5 May
stayAPT Suites Suffolk-Chesapeake
Interior

The Speakeasy Downtown Newport News

The Speakeasy Downtown Newport News
2.0 star property
Downtown Newport News
The price is ₹10,756
₹26,787 total
includes taxes & fees
23 Apr - 24 Apr
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

Coastal Hotel and Suites Virginia Beach Oceanfront

Coastal Hotel and Suites Virginia Beach Oceanfront

10/10 Excellent
"This has nothing to do with the property itself, but do your research on Virginia Beach and make sure that there’s not a curfew. There was one when we went and our entire trip was a plan to smoke cigars on the beach but we couldn’t do that because of the curfew the room was great. The view was perfect. We had the king suite with the ocean view on the ninth floor."
Dawna 1-night trip
Posted 1 hour ago
Coastal Hotel and Suites Virginia Beach Oceanfront

Find out more about Chesapeake

Holiday Rentals in Chesapeake

Search for holiday rentals in Chesapeake on Expedia.co.uk! You can easily find your home rentals, villas, holiday apartments in Chesapeake using one of the methods below:

  • View our selection of featured holiday rentals in Chesapeake
  • Use the map to find apartments and other holiday homes in the Chesapeake neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chesapeake while they last

Look no further and take a look at our great range of rental properties in Chesapeake!

Frequently asked questions

Are there holiday rentals in Chesapeake?

Yes, there are holiday rentals in Chesapeake close to Broadmoor 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 42 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 City Park are a couple of great spots to enjoy the outdoors. While in the area, you can also visit popular places such as Naval Station Norfolk and Sandbridge 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.