A golf course, a large building complex, and a marina by a river.

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Chesapeake holiday rentals

A modern kitchen with white cabinets, a stainless steel microwave, and a dining area with a round table and leather chairs.

1. 4BR Townhome in Riverfront Chesapeake Community

4BR Townhome in Riverfront Chesapeake Community
3.0 star property
Deep Creek South
4BR Townhome in Riverfront Chesapeake Community
A kitchen with wooden cabinets, stainless steel appliances, a granite countertop, and a window.

2. Entire Home in Chesapeake, Virginia

Entire Home in Chesapeake, Virginia
3.0 star property
Chesapeake
The price is ฿6,249
฿21,509 total
includes taxes & fees
9 Nov - 10 Nov
Entire Home in Chesapeake, Virginia
A modern courtyard with white furniture, a central seating area, and a small lawn.

3. stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
3.5 star property
Suffolk
9.6 out of 10, Exceptional, (114 reviews)
"Theophilus was great at check in. Amazing customer service, quick check-in. The place was clean, the rooms were very clean. The overall atmosphere was great. I will definitely stay here again."
United States
Tarina
The price is ฿4,019
฿4,616 total
includes taxes & fees
9 Nov - 10 Nov
stayAPT Suites Suffolk-Chesapeake
Private kitchen

4. stayAPT Suites Hampton

stayAPT Suites Hampton
2.5 star property
Coliseum Central
9.0 out of 10, Wonderful, (36 reviews)
"Great stay! Will be staying again!"
United States
Wakeelah
The price is ฿4,019
฿4,690 total
includes taxes & fees
29 Oct - 30 Oct
stayAPT Suites Hampton
A two-story house with a white porch, a red door, and a small Christmas tree.

5. Angie's Guest Cottage

Angie's Guest Cottage
2.0 star property
Northeast Virginia Beach
8.4 out of 10, Very good, (250 reviews)
"Not a top of the line hotel, but it was clean, good location, and it served our needs. We would definitely stay here again."
United States
Cheryl
The price is ฿2,675
฿3,474 total
includes taxes & fees
3 Nov - 4 Nov
Angie's Guest Cottage
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 Inn & Suites Hampton near Coliseum

Comfort Inn & Suites Hampton near Coliseum

10/10 Excellent
"Rooms were clean, staff is friendly everyone spoke. It was quiet i was able to get sleep. Very nice environment"
Lakeisha 2-night trip
Posted 3 hours ago
Comfort Inn & Suites Hampton near Coliseum

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:

  • View our selection of featured holiday rentals in Chesapeake
  • Use the map to find apartments and other holiday homes in the Chesapeake neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chesapeake while they last

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

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 Chesapeake City Park and Oak Grove Lake 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.