Chesapeake Vacation Rentals

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Check prices for these dates

In two weeks
Mar 13 - Mar 15
In two months
Apr 24 - Apr 26
In three months
May 22 - May 24
In four months
Jun 19 - Jun 21

Our top choices for Chesapeake vacation rentals

Terrace/patio

Aparthotel in Suffolk

stayAPT Suites Suffolk-Chesapeake
2.5 star property
9.4 out of 10, Exceptional, (63 reviews)
"The staff was so friendly. The rooms were so nice. I loved the kitchen and breakfast bar."
United States
Nicole
The price is NT$3,717
NT$4,269 total
includes taxes & fees
Mar 1 - Mar 2
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, (1,465 reviews)
"Clean and nice room"
United States
Curtis
The price is NT$1,784
NT$3,910 total
includes taxes & fees
Mar 18 - Mar 19
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, (1,193 reviews)
"We had a great stay. The staff was very helpful. The room was amazing and clean. We will be back"
United States
Rod
The price is NT$3,645
NT$6,050 total
includes taxes & fees
Mar 15 - Mar 16
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 NT$3,412
NT$5,782 total
includes taxes & fees
Mar 17 - Mar 18
The Atrium Resort, Virginia Beach by Vacatia
Apartment | 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 NT$3,360
NT$8,535 total
includes taxes & fees
Mar 2 - Mar 3
Ice Ice Baby Downtown Newport News
House (4 Bedrooms) | Interior

Cottage in Portsmouth

Centrally Located Hampton Roads Home w/ Game Room!
3.0 star property
The price is NT$8,215
NT$19,318 total
includes taxes & fees
Feb 28 - Mar 1
Centrally Located Hampton Roads Home w/ Game Room!
Property entrance

Apartment in Northeast Virginia Beach

Angie's Guest Cottage
2.0 star property
8.6 out of 10, Excellent, (227 reviews)
"The best place I have ever stayed at"
United States
Robin
The price is NT$2,474
NT$3,213 total
includes taxes & fees
Mar 1 - Mar 2
Angie's Guest Cottage
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 NT$3,295
NT$11,791 total
includes taxes & fees
Mar 2 - Mar 3
Buckroe Bungalow Buckroe Bungalow Escape to the Beach 2mins Away
Interior

Apartment in Sandbridge

4BR Waterfront Penthouse Pool Views
2.0 star property
The price is NT$10,620
NT$24,813 total
includes taxes & fees
Mar 2 - Mar 3
4BR Waterfront Penthouse Pool Views
Interior

Apartment in Downtown Newport News

The Speakeasy Downtown Newport News
2.0 star property
The price is NT$3,249
NT$8,387 total
includes taxes & fees
Mar 1 - Mar 2
The Speakeasy Downtown Newport News
Apartment | 1 bedroom

Apartment in Downtown Newport News

The Safe House Downtown Newport News
2.0 star property
6.0 out of 10, (1 review)
The price is NT$3,100
NT$8,189 total
includes taxes & fees
Mar 2 - Mar 3
The Safe House Downtown Newport News
Apartment | 2 bedrooms

Apartment in Downtown Newport News

Breakfast Tiffany s Downtown Newport News
2.0 star property
6.0 out of 10, (1 review)
"The property was nice but full of insects my kids didn’t want to sleep there. "
United States
James
The price is NT$2,653
NT$7,597 total
includes taxes & fees
Mar 1 - Mar 2
Breakfast Tiffany s Downtown Newport News
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

Schooner Inn

Schooner Inn

10/10 Excellent
"Rooms are always spotless,the staff is very"
Camille 2-night trip
Posted 2 days ago
Schooner Inn

Find out more about Chesapeake

Search for holiday rentals in Chesapeake on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesapeake using one of the methods below:

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Look no further and take a look at our great range of rental properties in Chesapeake!

Frequently asked questions

Are there vacation rentals in Chesapeake?

Yes, there are vacation rentals in Chesapeake close to Chesapeake Arboretum, or you can go with a more remote 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 vacation rentals are there in Chesapeake?

Expedia has 41 vacation 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 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 vacation rental in Chesapeake like?

Vacation rentals are privately owned properties you can stay in for a couple of days or more in Chesapeake. Vacation rentals feature amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from public hotel elevators and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for family trips.