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Search Holiday Rentals in Chesapeake

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Check prices for these dates

In two weeks
23 Jan - 25 Jan
In two months
6 Mar - 8 Mar
In three months
3 Apr - 5 Apr
In four months
1 May - 3 May

Our top choices for Chesapeake holiday rentals

Apartment | 2 bedrooms
The Speakeasy Downtown Newport News

Apartment in Downtown Newport News

The Speakeasy Downtown Newport News
2.0 star property
The price is 2.553.912 ₫
6.582.257 ₫ total
includes taxes & fees
10 Jan - 11 Jan
The Speakeasy Downtown Newport News
Beach nearby
The Atrium Resort, Virginia Beach by Vacatia

Aparthotel in Northeast Virginia Beach

The Atrium Resort, Virginia Beach by Vacatia
3.5 star property
8.2 out of 10, Very good, (1479)
"Staff was very nice and attentive!"
United States
Darryl
The price is 12.057.012 ₫
15.428.511 ₫ total
includes taxes & fees
22 Jan - 23 Jan
The Atrium Resort, Virginia Beach by Vacatia
Terrace/patio
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Aparthotel in Northeast Virginia Beach

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
3.0 star property
8.2 out of 10, Very good, (1180)
"The room was very clean and nice! Enjoyed the ocean view. We had nothing but positive interactions with the staff. It was very easy to use all the wonderful facilities such as the pool hot tub and the sauna."
United States
Bonnie
The price is 3.065.899 ₫
5.089.147 ₫ total
includes taxes & fees
21 Jan - 22 Jan
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
House (4 Bedrooms) | Interior
Centrally Located Hampton Roads Home w/ Game Room!

Cottage in Portsmouth

Centrally Located Hampton Roads Home w/ Game Room!
3.0 star property
The price is 6.910.325 ₫
16.250.037 ₫ total
includes taxes & fees
8 Jan - 9 Jan
Centrally Located Hampton Roads Home w/ Game Room!
Indoor pool
The Ocean Key Virginia Beach Resort

Aparthotel in Northeast Virginia Beach

The Ocean Key Virginia Beach Resort
3.0 star property
7.8 out of 10, Good, (1457)
"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
stayAPT Suites Suffolk-Chesapeake

Aparthotel in Suffolk

stayAPT Suites Suffolk-Chesapeake
2.5 star property
9.4 out of 10, Exceptional, (58)
"Beautiful and clean. The staff was amazing. "
United States
Robin
The price is 3.125.892 ₫
3.589.785 ₫ total
includes taxes & fees
19 Jan - 20 Jan
stayAPT Suites Suffolk-Chesapeake
Property entrance
Angie's Guest Cottage

Apartment in Northeast Virginia Beach

Angie's Guest Cottage
2.0 star property
8.6 out of 10, Excellent, (225)
"The best place I have ever stayed at"
United States
Robin
The price is 2.080.426 ₫
2.701.927 ₫ total
includes taxes & fees
19 Jan - 20 Jan
Angie's Guest Cottage
Studio | Interior
Beach Side Studio #3 Apts by RedAwning

Apartment in Cottage Line

Beach Side Studio #3 Apts by RedAwning
3.0 star property
The price is 1.893.639 ₫
5.132.397 ₫ total
includes taxes & fees
5 Feb - 6 Feb
Beach Side Studio #3 Apts by RedAwning
Studio | 3 bedrooms
Buckroe Bungalow Buckroe Bungalow Escape to the Beach 2mins Away

Apartment in Hampton

Buckroe Bungalow Buckroe Bungalow Escape to the Beach 2mins Away
2.0 star property
The price is 2.235.511 ₫
8.786.726 ₫ total
includes taxes & fees
11 Jan - 12 Jan
Buckroe Bungalow Buckroe Bungalow Escape to the Beach 2mins Away
Apartment | 4 bedrooms
Penthouse By The Sea Huge Home w Amazing Views

Apartment in Sandbridge

Penthouse By The Sea Huge Home w Amazing Views
2.0 star property
Penthouse By The Sea Huge Home w Amazing 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

Comfort Suites Chesapeake - Norfolk

Comfort Suites Chesapeake - Norfolk

10/10 Excellent
"Yes i will be coming back "
Geneva 1-night trip
Posted 3 days ago
Comfort Suites Chesapeake - Norfolk

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 39 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 Oak Grove Lake Park and Chesapeake Arboretum 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.