Chesapeake Holiday Rentals

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Our top choices for Chesapeake holiday rentals

2.0 star property
10.0 out of 10, Exceptional, (42 reviews)
"Our 2nd time staying at this place and will most likely be our go to for future stays when we’re in the area."
United States
James S.
The price is AU$402
includes taxes & fees
4 Feb - 5 Feb
3-bedroom home away from home in fabulous Chesapeake, Virginia.
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$263
includes taxes & fees
2 Feb - 3 Feb
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!
10.0 out of 10, Exceptional, (3 reviews)
"Impressed with the whole experience. "
United States
Patricia M.
The price is AU$245
includes taxes & fees
24 Jan - 25 Jan
Great Studio | Pool & Hot Tub. Your Next Vacation
The price is AU$300
includes taxes & fees
31 Jan - 1 Feb
1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
The price is AU$231
includes taxes & fees
9 Feb - 10 Feb
Studio | Free Breakfast. Indoor Pool & Hot Tub
The price is AU$258
includes taxes & fees
31 Jan - 1 Feb
Studio | Free Breakfast. Indoor Pool & Hot Tub.
The price is AU$263
includes taxes & fees
2 Feb - 3 Feb
Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
10.0 out of 10, Exceptional, (1 review)
"Very clean , great location. Will stay there again!!!"
United States
Tony H.
The price is AU$249
includes taxes & fees
2 Feb - 3 Feb
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

Mobile Home in Sandbridge

Comfortable Beach Trailer Home
9.2 out of 10, Wonderful, (80 reviews)
"There were three of us staying there, and we couldn't have been more comfortable and enjoyed the stay more. Loved the space! Loved the area! A great place for a vacation!"
United States
Joseph V.
The price is AU$590
includes taxes & fees
31 Jan - 1 Feb
Comfortable Beach Trailer Home

Mobile Home in Sandbridge

Luxurious RV
8.4 out of 10, Very good, (17 reviews)
"Excellent accommodation close to beach I would stay here again !!! "
United States
Scott E.
The price is AU$590
includes taxes & fees
19 Jan - 20 Jan
Luxurious RV

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$361
includes taxes & fees
19 Jan - 20 Jan
Ice Ice Baby Downtown Newport News
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"The apartment was excellent! It was clean and well stocked with everything we need. The staff communicated very well. We were very satisfied and enjoyed our stay. Thank you so much for making our trip so good!"
United States
Jerrie W.
The price is AU$512
includes taxes & fees
19 Jan - 20 Jan
Sojourn's Harborage Jellyfish Suite Near Beach
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$135
includes taxes & fees
31 Jan - 1 Feb
Cozy 1-bedroom only in shared apartment with AC, WiFi in welcoming Norfolk
10.0 out of 10, Exceptional, (16 reviews)
"It was a great stay. Was there for work. Close for work and close to the beach. "
United States
Clayton M.
The price is AU$442
includes taxes & fees
20 Jan - 21 Jan
Comfortable & Private 2 Bedrm Cottage w/ King bed.

Apartment in East Ocean View

OV Mosaic - River Suite
9.2 out of 10, Wonderful, (7 reviews)
"Great place and cool area"
United States
Matt W.
The price is AU$471
includes taxes & fees
2 Feb - 3 Feb
OV Mosaic - River Suite
2.0 star property
The price is AU$1,432
includes taxes & fees
19 Jan - 20 Jan
902 C Coastal King Retreat Steps from Beach + Sauna
9.6 out of 10, Exceptional, (4 reviews)
"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$396
includes taxes & fees
20 Jan - 21 Jan
Charming 1-Bedroom 1-Bath Unit with Beautiful Riverfront Sunsets in Portsmouth
10.0 out of 10, Exceptional, (2 reviews)
"Great place. Nice area. Parking was confusing at first but host was very responsive "
United States
Ed and Laura S.
The price is AU$281
includes taxes & fees
23 Jan - 24 Jan
Private 1 Bed Apt - Historic Olde Towne Portsmouth

Holiday Home in Willoughby Spit

Water Front Delight on the Bay
7.8 out of 10, Good, (25 reviews)
"Everything was very nice really enjoyed "
United States
Deborah B.
The price is AU$478
includes taxes & fees
26 Jan - 27 Jan
Water Front Delight on the Bay
2.0 star property
9.8 out of 10, Exceptional, (257 reviews)
"We enjoyed a nice long weekend away and were able to bring our dog. The house was very cozy and well equipped. We were just a short walk to the beach which our puppy loved!!"
United States
Dawn W.
The price is AU$572
includes taxes & fees
1 Feb - 2 Feb
Steps to the Ocean! A Family and Dog-Friendly Cottage Duplex in the North End
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$192 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?

Oceanfront home “Sea Watch” ~~brand new pool: 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 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of an arcade/games room in this rental home to help you unwind.

How many holiday rentals are there in Chesapeake?

Expedia has 39 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. 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.