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Chesapeake Vacation Rentals

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Check prices for these dates

Tonight
24 Dec - 25 Dec
Tomorrow
25 Dec - 26 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Chesapeake holiday rentals

Terrace/patio
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
3.0 star property
Northeast Virginia Beach
8.2 out of 10, Very good, (1175)
"Staff was very attentive and welcoming! Very clean, such a great place!!"
United States
michelle
The price is RM471
RM784 total
includes taxes & fees
28 Dec - 29 Dec
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
Indoor pool
The Ocean Key Virginia Beach Resort

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, (1457)
"Great stay, great recovery from other ocean front places! Great room for a family or girls sleepover!!"
United States
Aja-Brianne A
The Ocean Key Virginia Beach Resort
Property entrance
Angie's Guest Cottage

Angie's Guest Cottage

Angie's Guest Cottage
2.0 star property
Northeast Virginia Beach
8.6 out of 10, Excellent, (225)
"Will definitely stay again. Very very clean and everyone was so amazing and welcoming. "
United States
Patricia
The price is RM322
RM418 total
includes taxes & fees
29 Dec - 30 Dec
Angie's Guest Cottage
2 bedrooms
Ice Ice Baby Downtown Newport News

Ice Ice Baby Downtown Newport News

Ice Ice Baby Downtown Newport News
2.0 star property
Downtown Newport News
10.0 out of 10, Exceptional, (2)
"Loved the place.. clean and quiet!! Perfect for a weekend getaway "
United States
Nicole
The price is RM456
RM1,099 total
includes taxes & fees
28 Dec - 29 Dec
Ice Ice Baby Downtown Newport News
Beach nearby
The Atrium Resort, Virginia Beach by Vacatia

The Atrium Resort, Virginia Beach by Vacatia

The Atrium Resort, Virginia Beach by Vacatia
3.5 star property
Northeast Virginia Beach
8.2 out of 10, Very good, (1479)
"Staff was very nice and attentive!"
United States
Darryl
The price is RM1,864
RM2,385 total
includes taxes & fees
7 Jan - 8 Jan 2026
The Atrium Resort, Virginia Beach by Vacatia
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

La Quinta Inn & Suites by Wyndham Virginia Beach

La Quinta Inn & Suites by Wyndham Virginia Beach

10/10 Excellent
"Room was clean and very nice. Close to the beach as well "
Jaime Joel 1-night trip
Posted 2 days ago
La Quinta Inn & Suites by Wyndham Virginia Beach

Find out more about 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 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.