Chesapeake Holiday Rentals

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Our top choices for Chesapeake holiday rentals

The price is AU$237
includes taxes & fees
11 Mar - 12 Mar
Studio | Free Breakfast. Indoor Pool & Hot Tub
10.0 out of 10, Exceptional, (43 reviews)
"This was a wonderful place that was perfect for girls trip! I would definitely recommend and stay again!!"
United States
Tabitha P.
3-bedroom home away from home in fabulous Chesapeake, Virginia.
The price is AU$329
includes taxes & fees
2 Apr - 3 Apr
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!
10.0 out of 10, Exceptional, (3 reviews)
"Impressed with the whole experience. "
United States
Patricia M.
The price is AU$234
includes taxes & fees
9 Mar - 10 Mar
Great Studio | Pool & Hot Tub. Your Next Vacation
The price is AU$331
includes taxes & fees
4 Apr - 5 Apr
1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
9.0 out of 10, Wonderful, (2 reviews)
"Very clean , great location. Will stay there again!!!"
United States
Tony H.
The price is AU$280
includes taxes & fees
5 Apr - 6 Apr
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
8.0 out of 10, Very good, (4 reviews)
"Perfect for what we needed for one day layover before outer Banks"
Canada
Michael L.
The price is AU$272
includes taxes & fees
8 Mar - 9 Mar
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!

Apartment in Downtown Newport News

The Speakeasy Downtown Newport News
2.0 star property
The Speakeasy Downtown Newport News
9.8 out of 10, Exceptional, (17 reviews)
"Very clean, the beds were comfortable! It was a great place to stay!"
United States
Lee S.
The price is AU$420
includes taxes & fees
8 Mar - 9 Mar
Comfortable & Private 2 Bedrm Cottage w/ King bed.
9.6 out of 10, Exceptional, (5 reviews)
"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$326
includes taxes & fees
6 Mar - 7 Mar
Knot Three- Balcony View of ICW- Dog Friendly!

Holiday Home in Northeast Virginia Beach

The Art Door Duplex only minutes from beach
9.6 out of 10, Exceptional, (108 reviews)
"The rooms were very clean and be was comfortable!"
United States
CYMANDYE V.
The price is AU$330
includes taxes & fees
12 Mar - 13 Mar
The Art Door Duplex only minutes from beach
The price is AU$550
includes taxes & fees
9 Mar - 10 Mar
Wild Horses - 4x4 Beach - Quiet & Cozy
9.8 out of 10, Exceptional, (15 reviews)
"This was a beautiful property. Plenty of room for Family Fun and very close to the beach. The host was very helpful and communicated with us about the property. I would definitely stay here again. "
United States
Tamika H.
The price is AU$573
includes taxes & fees
10 Mar - 11 Mar
Beach Bungalow King Bed 1 Floor Living

Holiday Home in Willoughby Spit

Sojourn | Coastal Cottage | 3 BR
9.4 out of 10, Exceptional, (34 reviews)
"The house was clean and had everything you need. The neighborhood was quiet. Beach access was just a short walk away and not crowded. "
United States
Daniel P.
The price is AU$607
includes taxes & fees
11 Mar - 12 Mar
Sojourn | Coastal Cottage | 3 BR
10.0 out of 10, Exceptional, (2 reviews)
"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
31 Mar - 1 Apr
Cozy 1-bedroom only in shared apartment with AC, WiFi in welcoming Norfolk
8.6 out of 10, Excellent, (7 reviews)
"Cute little bungalow on the beach. Beautiful sunrises. Location is great. Very clean. Has everything you need!!! The pier is a 2 min walk. "
United States
Virginia T.
The price is AU$323
includes taxes & fees
8 Mar - 9 Mar
Beachfront Bungalow w/ BEST Location in Ocean View!
9.0 out of 10, Wonderful, (8 reviews)
"Loved watching the yachts in the ICW"
United States
susan
The price is AU$316
includes taxes & fees
6 Mar - 7 Mar
Knot One- Balcony View of ICW- Dog Friendly!

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 AU$402
includes taxes & fees
8 Mar - 9 Mar
Ice Ice Baby Downtown Newport News
9.4 out of 10, Exceptional, (3 reviews)
"Host is communicative and relaxed (not trying to micromanage your stay). I forgot to check the pics and descriptions for a microwave but there isn’t one. Alternatively, there is a hot plate and a pot. I gave 4 out of 5 stars due to the coffeemaker not working and having one washcloth for two people but it was pleasant other than that. "
United States
Courtney R.
The price is AU$283
includes taxes & fees
9 Mar - 10 Mar
Charming 1-bedroom in-law suite with functional kitchen in pleasant Portsmouth

Holiday Home in Bayview

Cozy Beach Home in Oceanview
9.8 out of 10, Exceptional, (46 reviews)
"Loved staying here. The house had everything that was needed and it was in close proximity to everything. "
United States
Conor L.
The price is AU$465
includes taxes & fees
8 Mar - 9 Mar
Cozy Beach Home in Oceanview
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$145 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 Chesapeake Arboretum, 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?

The Art Door Duplex only minutes from beach: This holiday home rental outside of Chesapeake comes with air conditioning so that you can feel at home during your trip.

How many holiday rentals are there in Chesapeake?

Expedia has 41 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 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.