Chesapeake Holiday Rentals

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Tonight
12 Jun - 13 Jun
Tomorrow
13 Jun - 14 Jun
This weekend
13 Jun - 15 Jun
Next weekend
20 Jun - 22 Jun

Holiday Rentals in Chesapeake

The Ocean Key Virginia Beach Resort
Indoor pool

The Ocean Key Virginia Beach Resort

3.0 star property
7.8 out of 10, Good, (1349)
"Staff was friendly, nice rooms"
The price is S$224
includes taxes & fees
25 Jun - 26 Jun
The Ocean Key Virginia Beach Resort
The Atrium Resort, Virginia Beach by Vacatia
Beach nearby

The Atrium Resort, Virginia Beach by Vacatia

3.5 star property
8.2 out of 10, Very good, (1349)
"perfect location and comfortable stays "
The Atrium Resort, Virginia Beach by Vacatia
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
Terrace/patio

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

3.0 star property
8.2 out of 10, Very good, (1077)
"very friendly, nice location"
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
stayAPT Suites Suffolk-Chesapeake
Terrace/patio

stayAPT Suites Suffolk-Chesapeake

2.5 star property
9.8 out of 10, Exceptional, (16)
"Great place to stay!"
The price is S$175
includes taxes & fees
30 Jun - 1 Jul
stayAPT Suites Suffolk-Chesapeake
Angie's Guest Cottage
Property entrance

Angie's Guest Cottage

2.0 star property
8.6 out of 10, Excellent, (203)
"Owners were very accomodating with our late arrival."
The price is S$177
includes taxes & fees
15 Jun - 16 Jun
Angie's Guest Cottage
Four Sails Resort
On the beach

Four Sails Resort

3.5 star property
7.6 out of 10, Good, (35)
"Very nice place"
The price is S$587
includes taxes & fees
15 Jun - 16 Jun
Four Sails Resort
The Colony at Virginia Beach
Balcony view

The Colony at Virginia Beach

2.5 star property
2.0 out of 10, (1)
"The rental unit was falling apart. I've never seen a dump like this place. There was a maintenance request from the previous renters (which was dated May 31, we got there June 4) that stated there were bed bugs. And a host of other problems. We left immediately after calling the properties management, who never responded. On a scale of 1 to 100 I'd give this place a 5. "
The Colony at Virginia Beach
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 39 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.