Chesapeake Holiday Rentals

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Check prices for these dates

In two weeks
3 Apr - 5 Apr
In two months
15 May - 17 May
In three months
12 Jun - 14 Jun
In four months
10 Jul - 12 Jul

Our top choices for Chesapeake holiday rentals

Terrace/patio

Aparthotel in Suffolk

stayAPT Suites Suffolk-Chesapeake
2.5 star property
9.4 out of 10, Exceptional, (69 reviews)
"perfect stay. would definitely stay again "
United States
berry
The price is S$175
includes taxes & fees
23 Mar - 24 Mar
stayAPT Suites Suffolk-Chesapeake
Indoor pool

Aparthotel in Northeast Virginia Beach

The Ocean Key Virginia Beach Resort
3.0 star property
7.8 out of 10, Good, (1,474 reviews)
"Very easy check in, pool was nice and convenient for kids, great location to beach"
United States
Porsch
The Ocean Key Virginia Beach Resort
Beach/ocean view

Aparthotel in Northeast Virginia Beach

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
4.0 star property
8.2 out of 10, Very good, (1,201 reviews)
"Location was great, room was clean, and the hot tub and pool topped it all off"
United States
James
The price is S$247
includes taxes & fees
5 Apr - 6 Apr
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
Beach nearby

Aparthotel in Northeast Virginia Beach

The Atrium Resort, Virginia Beach by Vacatia
3.5 star property
8.2 out of 10, Very good, (1,479 reviews)
"Clean, spacious, short walk to beach, nice staff, I will be back definitely "
United States
Sy
The price is S$223
includes taxes & fees
2 Apr - 3 Apr
The Atrium Resort, Virginia Beach by Vacatia
On the beach, beach towels

Apartment in Hampton

Buckroe Bungalow Buckroe Bungalow Escape to the Beach 2mins Away
2.0 star property
The price is S$549
includes taxes & fees
23 Mar - 24 Mar
Buckroe Bungalow Buckroe Bungalow Escape to the Beach 2mins Away
Property entrance

Apartment in Northeast Virginia Beach

Angie's Guest Cottage
2.0 star property
8.6 out of 10, Excellent, (228 reviews)
"The best place I have ever stayed at"
United States
Robin
The price is S$131
includes taxes & fees
22 Mar - 23 Mar
Angie's Guest Cottage
Free WiFi

Apartment in Cottage Park

Beach Side Studio #2 Apts by RedAwning
3.0 star property
Beach Side Studio #2 Apts by RedAwning
2 bedrooms

Apartment in Downtown Newport News

Ice Ice Baby Downtown Newport News
2.0 star property
10.0 out of 10, Exceptional, (2 reviews)
"Loved the place.. clean and quiet!! Perfect for a weekend getaway "
United States
Nicole
The price is S$386
includes taxes & fees
22 Mar - 23 Mar
Ice Ice Baby Downtown Newport News
Interior

Apartment in Downtown Newport News

The Speakeasy Downtown Newport News
2.0 star property
The price is S$309
includes taxes & fees
22 Mar - 23 Mar
The Speakeasy Downtown Newport News
Interior

Apartment in Sandbridge

4BR Waterfront Penthouse Pool Views
2.0 star property
The price is S$1,180
includes taxes & fees
23 Mar - 24 Mar
4BR Waterfront Penthouse Pool Views
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
"We absolutely love the location. Everything is clean and fresh. We love the pet friendly atmosphere. Rooms are awesome, beds are comfortable, shower was great, and had just what we needed. we stayed an additional day, as we liked it so much. "
Tasha 1-night trip
Posted 1 hour 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 40 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 Lake Drummond 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.