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Search Holiday Rentals in Chesapeake

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Check prices for these dates

Tonight
22 Nov - 23 Nov
Tomorrow
23 Nov - 24 Nov
Next weekend
28 Nov - 30 Nov
In two weeks
5 Dec - 7 Dec

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 2.608.437 ₫
4.568.241 ₫ total
includes taxes & fees
23 Nov - 24 Nov
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 2.720.558 ₫
3.458.093 ₫ 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, (53)
"Excellent hotel. I will definitely stay there again. "
United States
Leta
The price is 3.137.078 ₫
3.602.631 ₫ total
includes taxes & fees
25 Nov - 26 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 2.087.870 ₫
2.711.595 ₫ total
includes taxes & fees
23 Nov - 24 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

Hyatt Place Virginia Beach / Oceanfront

Hyatt Place Virginia Beach / Oceanfront

10/10 Excellent
"Clean and spacious rooms. Nice beach view and very helpful staff! Loved my experience! "
Aby 2-night trip
Posted 1 day ago
Hyatt Place Virginia Beach / Oceanfront

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 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 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.