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

Chesapeake Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Chesapeake holiday rentals

A living room with a sofa, armchair, coffee table, and fireplace.

1. Nyakio Suite

Nyakio Suite
2.0 star property
Greenbrier
Nyakio Suite
A modern courtyard with white furniture, a central seating area, and a small lawn.

2. stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
3.5 star property
Suffolk
9.6 out of 10, Exceptional, (112 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 AU$195
includes taxes & fees
29 Oct - 30 Oct
stayAPT Suites Suffolk-Chesapeake
An outdoor seating area with wicker furniture and orange Adirondack chairs.

3. Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
4.0 star property
Northeast Virginia Beach
8.2 out of 10, Very good, (1,447 reviews)
"Great stay"
United States
Nancy
The price is AU$301
includes taxes & fees
4 Nov - 5 Nov
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
A multi-story building with balconies, a courtyard with seating, and a well-maintained lawn.

4. stayAPT Suites Hampton

stayAPT Suites Hampton
2.5 star property
Coliseum Central
9.0 out of 10, Wonderful, (32 reviews)
"Great stay! Comfortable & close to a lot of stores & restaurants"
United States
Vanessa
The price is AU$174
includes taxes & fees
10 Nov - 11 Nov
stayAPT Suites Hampton
An indoor swimming pool with clear glass ceilings, lounge chairs, and a view of the outside.

5. The Ocean Key Virginia Beach Resort

The Ocean Key Virginia Beach Resort
3.0 star property
Northeast Virginia Beach
7.6 out of 10, Good, (1,687 reviews)
"The room was nice and spacious. The hot tub wasn't working. Overall a great place to stay."
United States
Sharon
The price is AU$151
includes taxes & fees
3 Nov - 4 Nov
The Ocean Key Virginia Beach Resort
A two-story house with a white porch, a red door, and a small Christmas tree.

6. 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 AU$146
includes taxes & fees
26 Oct - 27 Oct
Angie's Guest Cottage
A pool table in a room with wooden floors, a fireplace, and a window with purple curtains.

7. Centrally Located Hampton Roads Home w/ Game Room!

Centrally Located Hampton Roads Home w/ Game Room!
3.0 star property
Portsmouth
Centrally Located Hampton Roads Home w/ Game Room!
A modern house with a wooden exterior, a glass door, and a stone pathway leading to the entrance.

8. Private Virginia Beach Escape w/ Pool & Fire Pit!

Private Virginia Beach Escape w/ Pool & Fire Pit!
3.5 star property
Virginia Beach
The price is AU$751
includes taxes & fees
23 Oct - 24 Oct
Private Virginia Beach Escape w/ Pool & Fire Pit!
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

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

10/10 Excellent
"The room was clean and wonderful! The beds and pillows were very comfortable. The views from the big window and balcony were beautiful. And the walks were so convenient and enjoyable. I would definitely return here again!"
Vicki 3-night trip
Posted 1 hour ago
Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

Find out more about Chesapeake

Everything you need to know about Chesapeake holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chesapeake holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesapeake holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chesapeake holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesapeake. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesapeake holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesapeake holiday rentals we have selected for you start as low as AU$146 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chesapeake rentals

At Expedia, we put the best Chesapeake holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chesapeake rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesapeake holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesapeake. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.

What are some of the best holiday rentals that Chesapeake has to offer?

Salted Dunes OBX, Beach front, Wild Horses, Pool, Hot Tub, 4x4 Beach, 7 Bedroom: This holiday home rental outside of Chesapeake is located on the beach, and has an outdoor pool, a patio and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with an arcade/games room and 1 hot tub.

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.