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Chesapeake Holiday Rentals

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Holiday Rentals in Chesapeake

Holiday Home in Chesapeake

2.0 star property
10.0 out of 10, Exceptional, (39)
"Everything was great! "
United States
Nikki S.
The price is AU$395
includes taxes & fees
9 Dec - 10 Dec
3-bedroom home away from home in fabulous Chesapeake, Virginia.

Apartment in Willoughby Spit

10.0 out of 10, Exceptional, (2)
"very friendly host! very patient with me on day of check in, made sure we had everything we needed & more !"
United States
Shydymond B.
The price is AU$137
includes taxes & fees
4 Dec - 5 Dec
Cozy 1-bedroom only in shared apartment with AC, WiFi in welcoming Norfolk

Apartment in East Ocean View

2.0 star property
10.0 out of 10, Exceptional, (2)
"Me and my family enjoyed our beach stay. There was a beach in walking distance to the house, a playground and also a store. We drove to Virginia Beach for one day which was about a 30 minute drive. We enjoyed the beach in the back of the house more. The host responds quick when asked questions. I would recommend and will be staying next summer again with my family. "
United States
Brandee S.
The price is AU$517
includes taxes & fees
7 Dec - 8 Dec
Sojourn's Harborage Coral Suite

Apartment in Newport News

2.0 star property
The price is AU$343
includes taxes & fees
8 Dec - 9 Dec
The Speakeasy Downtown Newport News

Cabin in Shawboro

8.8 out of 10, Excellent, (23)
"quiet, remote cabin full of personality. Great if you want to be AWAY from people"
United States
Jamie F.
The price is AU$390
includes taxes & fees
7 Dec - 8 Dec
Cabin in the Woods, Pet Friendly

Holiday Home in Portsmouth

9.6 out of 10, Exceptional, (4)
"Property is well maintained. Great AC. Perfect for a couple to get away for a week. Central location was perfect for everything we planned to do for the week. "
United States
Paige M.
The price is AU$404
includes taxes & fees
5 Dec - 6 Dec
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth

Apartment in Cottage Park

7.8 out of 10, Good, (16)
"Cute structure, awesome location. Not well maintained. Bugs abound. Amazing price!"
United States
Stewart S.
The price is AU$231
includes taxes & fees
22 Dec - 23 Dec
Beach Side Studio #3 - Pet Friendly, WiFi, Off-Street Parking, Large Smart TV

Holiday Home in Coinjock

9.6 out of 10, Exceptional, (4)
"The whole process was very easy and smooth. The property was clean and comfortable. I would definitely stay here again in the future!"
United States
Pam P.
The price is AU$343
includes taxes & fees
9 Dec - 10 Dec
Knot Three- Balcony View of ICW- Dog Friendly!

Holiday Home in Northeast Virginia Beach

9.6 out of 10, Exceptional, (104)
"Great get away stay! Close drive to the shops and the beach. Very cozy. Would definitely stay there again!"
United States
Lizy G.
The price is AU$351
includes taxes & fees
8 Dec - 9 Dec
The Art Door only minutes from beach

Holiday Home in Hampton

9.0 out of 10, Wonderful, (18)
"Conveniently located by the beach and fun ocean color scheme. The "
United States
Hannah O.
The price is AU$513
includes taxes & fees
8 Dec - 9 Dec
#Buckroe Bungalow ~Escape to the Beach 2mins Away!

Apartment in Coinjock

9.0 out of 10, Wonderful, (7)
"Loved watching the yachts in the ICW"
United States
susan
The price is AU$333
includes taxes & fees
4 Dec - 5 Dec
Knot One- Balcony View of ICW- Dog Friendly!

Apartment in Portsmouth

9.0 out of 10, Wonderful, (34)
"Easy access to everything"
United States
Latoya J.
The price is AU$384
includes taxes & fees
4 Dec - 5 Dec
Historic Olde Towne 2 Bedroom 1 Bath 1100sq ft Vacation Rental

Cottage in Willoughby Spit

2.0 star property
The price is AU$1,610
includes taxes & fees
4 Dec - 5 Dec
900. B Seaside 2 Br Cottage with Bay Views, Veranda, High Ceilings, Hot Tub, Private Beach, Beachfront Grilling, & Kayaks

Holiday Home in Wythe

7.8 out of 10, Good, (10)
"Clean, convenient and comfortable, would stay again."
United States
Riley
The price is AU$411
includes taxes & fees
8 Dec - 9 Dec
Large 2 bedroom | Queen beds | Safe Area

Holiday Home in Coinjock

10.0 out of 10, Exceptional, (36)
"Cute, clean and well appointed. The view over the water is so pretty. We would stay again! "
United States
Susan H.
The price is AU$397
includes taxes & fees
4 Dec - 5 Dec
Waterview Cottage on the Currituck Sound with Private Dock & Kayaks

Cottage in East Ocean View

9.0 out of 10, Wonderful, (277)
"Great for our very busy boys--right across the street from the beach, 3 min walk to a very clean, fun park. Quick drive to stores. Easy to get in/out of the house, plently of comfy beds and amenities. "
United States
Kaila S.
The price is AU$614
includes taxes & fees
4 Dec - 5 Dec
Norfolk Beach Cottage Rental

Apartment in Portsmouth

10.0 out of 10, Exceptional, (2)
"Great place. Nice area. Parking was confusing at first but host was very responsive "
United States
Ed and Laura S.
The price is AU$321
includes taxes & fees
10 Dec - 11 Dec
Private 1 Bed Apt - Historic Olde Towne Portsmouth

Apartment in Cottage Park

8.2 out of 10, Very good, (20)
"It was conveniently located to anything we traveled to. "
United States
Margaret P.
The price is AU$453
includes taxes & fees
18 Dec - 19 Dec
Sojourn 1 BR Beach Home with Private Beach Access

Holiday Home in Portsmouth

9.0 out of 10, Wonderful, (22)
"Great property "
United States
Brian C.
The price is AU$443
includes taxes & fees
17 Dec - 18 Dec
Charming 2 bedroom, 2 bath townhome located in Portsmouth, Simple and elegant!!
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

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$156 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?

Trendy home steps from beach access w/private outdoor pool, gas grill, balcony: This holiday home rental outside of Chesapeake is located near the beach, and has a balcony, a BBQ and air conditioning to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Chesapeake?

Expedia has 38 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 Oak Grove Lake Park and Chesapeake City Park 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.