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Check prices for these dates

Tonight
19 Nov - 20 Nov
Tomorrow
20 Nov - 21 Nov
This weekend
21 Nov - 23 Nov
Next weekend
28 Nov - 30 Nov

Top Holiday Rentals in Chesapeake

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, (1451)
"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
Terrace/patio
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, (1168)
"Staff was very attentive and welcoming! Very clean, such a great place!!"
United States
michelle
The price is ฿3,254
฿5,669 total
includes taxes & fees
3 Dec - 4 Dec
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
Indoor pool
Four Sails Resort

Four Sails Resort

4.0 star property
Northeast Virginia Beach
7.6 out of 10, Good, (49)
"Sweet little spot for the price. Easy parking"
United States
Jon
The price is ฿3,601
฿4,558 total
includes taxes & fees
26 Nov - 27 Nov
Four Sails Resort
Terrace/patio
stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake

2.5 star property
Suffolk
9.4 out of 10, Exceptional, (52)
"Nice cozy place to go with your family "
United States
Kesha
The price is ฿3,853
฿4,425 total
includes taxes & fees
23 Nov - 24 Nov
stayAPT Suites Suffolk-Chesapeake
Property entrance
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 ฿2,565
฿3,331 total
includes taxes & fees
20 Nov - 21 Nov
Angie's Guest Cottage
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

Comfort Suites Chesapeake - Norfolk

Comfort Suites Chesapeake - Norfolk

10/10 Excellent
"Staff was extremely courteous. "
Russell 2-night trip
Posted 1 day ago
Comfort Suites Chesapeake - Norfolk

Find out more about Chesapeake

Search for holiday rentals in Chesapeake on Expedia! 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 Bryant Farms Park, 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 Bryant Farms Park and Broadmoor Play Area, whereas Chesapeake City Park and Oak Grove Lake Park 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.