Search Holiday Rentals in Chesapeake

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Check prices for these dates

In two weeks
10 Oct - 12 Oct
In one month
24 Oct - 26 Oct
In two months
21 Nov - 23 Nov
In three months
19 Dec - 21 Dec

Top Holiday Rentals in Chesapeake

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, (1151)
"We love staying here everyone is very helpful and it’s right in the middle of the boardwalk "
The price is 3.486.252 ₫
5.580.822 ₫ total
includes taxes & fees
12 Oct - 13 Oct
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
The Ocean Key Virginia Beach Resort
Indoor pool

The Ocean Key Virginia Beach Resort

3.0 star property
7.8 out of 10, Good, (1434)
"Check in was very easy and staff super friendly and helpful. Location was great. Rooms are a bit dated but clean and bed was comfortable. Loved having a kitchen area in the little suite. "
The price is 2.449.581 ₫
4.388.829 ₫ total
includes taxes & fees
14 Oct - 15 Oct
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, (1469)
"My stay at the atrium was well, very nice staff and helpful with all my needs. "
The price is 2.113.402 ₫
4.002.225 ₫ total
includes taxes & fees
12 Oct - 13 Oct
The Atrium Resort, Virginia Beach by Vacatia
Four Sails Resort
Indoor pool

Four Sails Resort

4.0 star property
7.6 out of 10, Good, (43)
"It was peaceful"
The price is 3.569.852 ₫
4.474.251 ₫ total
includes taxes & fees
5 Oct - 6 Oct
Four Sails Resort
Angie's Guest Cottage
Property entrance

Angie's Guest Cottage

2.0 star property
8.6 out of 10, Excellent, (224)
"Central location to boardwalk music venues. Friendly staff, clean, quiet. "
The price is 1.976.824 ₫
2.584.082 ₫ total
includes taxes & fees
29 Sept - 30 Sept
Angie's Guest Cottage
stayAPT Suites Suffolk-Chesapeake
Terrace/patio

stayAPT Suites Suffolk-Chesapeake

2.5 star property
9.4 out of 10, Exceptional, (46)
"Nice cozy place to go with your family "
The price is 3.143.266 ₫
3.609.737 ₫ total
includes taxes & fees
28 Sept - 29 Sept
stayAPT Suites Suffolk-Chesapeake
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

Oceanfront Inn

Oceanfront Inn

10/10 Excellent
"I would stay again at Ocean Front when I visit VA Beach "
Marcella 2-night trip
Posted 14 hours ago
Oceanfront Inn

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 36 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.