Holiday Rentals in Chesapeake

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Our top choices for Chesapeake holiday rentals

3-bedroom home away from home in fabulous Chesapeake, Virginia.

3-bedroom home away from home in fabulous Chesapeake, Virginia.
Chesapeake
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.

Great Studio | Pool & Hot Tub. Your Next Vacation

Great Studio | Pool & Hot Tub. Your Next Vacation
Chesapeake
10.0 out of 10, Exceptional, (3 reviews)
"Impressed with the whole experience. "
United States
Patricia M.
Great Studio | Pool & Hot Tub. Your Next Vacation

Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!

Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!
Chesapeake
8.0 out of 10, Very good, (4 reviews)
"Perfect for what we needed for one day layover before outer Banks"
Canada
Michael L.
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
Chesapeake
1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

Studio | Free Breakfast. Indoor Pool & Hot Tub

Studio | Free Breakfast. Indoor Pool & Hot Tub
Chesapeake
Studio | Free Breakfast. Indoor Pool & Hot Tub

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Chesapeake
10.0 out of 10, Exceptional, (1 review)
"Very clean , great location. Will stay there again!!!"
United States
Tony H.
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Chesapeake
Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

Comfortable Beach Trailer Home

Comfortable Beach Trailer Home
Sandbridge
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.
Comfortable Beach Trailer Home

Luxurious RV

Luxurious RV
Sandbridge
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 €336
includes taxes & fees
4 Mar - 5 Mar
Luxurious RV

Comfortable & Private 2 Bedrm Cottage w/ King bed.

Comfortable & Private 2 Bedrm Cottage w/ King bed.
Portsmouth
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 €254
includes taxes & fees
8 Feb - 9 Feb
Comfortable & Private 2 Bedrm Cottage w/ King bed.

OV Mosaic - Topaz Suite

OV Mosaic - Topaz Suite
East Ocean View
10.0 out of 10, Exceptional, (2 reviews)
"We had a wonderful stay in Norfolk, Virginia, at OV. The room was very clean, exactly as described, and just a very short walk to the beach. We brought our dog, and the area was perfect for walks and relaxing. Communication with the property manager was excellent, and the location couldn’t have been better. Would definitely stay again!"
United States
Jose V.
OV Mosaic - Topaz Suite

The Art Door Duplex only minutes from beach

The Art Door Duplex only minutes from beach
Northeast Virginia Beach
9.6 out of 10, Exceptional, (105 reviews)
"The rooms were very clean and be was comfortable!"
United States
CYMANDYE V.
The price is €197
includes taxes & fees
9 Feb - 10 Feb
The Art Door Duplex only minutes from beach

The Speakeasy Downtown Newport News

The Speakeasy Downtown Newport News
2.0 star property
Downtown Newport News
The price is €221
includes taxes & fees
8 Feb - 9 Feb
The Speakeasy Downtown Newport News

Cozy 1-bedroom only in shared apartment with AC, WiFi in welcoming Norfolk

Cozy 1-bedroom only in shared apartment with AC, WiFi in welcoming Norfolk
Willoughby Spit
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 €84
includes taxes & fees
21 Feb - 22 Feb
Cozy 1-bedroom only in shared apartment with AC, WiFi in welcoming Norfolk

Cozy Bay Cottage private backyard blocks from beach!

Cozy Bay Cottage private backyard blocks from beach!
Bayview
9.0 out of 10, Wonderful, (43 reviews)
"Beautiful home! Spacious and very clean! Short walk to the beach! And very close to Virginia Beach board walk! Highly recommend for all!"
United States
Elizabeth B.
The price is €313
includes taxes & fees
7 Feb - 8 Feb
Cozy Bay Cottage private backyard blocks from beach!

OV Mosaic - River Suite

OV Mosaic - River Suite
East Ocean View
9.2 out of 10, Wonderful, (7 reviews)
"Great place and cool area"
United States
Matt W.
OV Mosaic - River Suite

Sojourn's Harborage unit 6

Sojourn's Harborage unit 6
East Ocean View
9.2 out of 10, Wonderful, (5 reviews)
"Very comfortable - beds were soft, sheets were great and water pressure was nice. There was a problem with city drains so the parking lot was flooded a couple nights, which caused a lot of dirt to be tracked into the unit, but this wasn't a problem with the rental. Location was close to everything we needed."
United States
Ronald K.
The price is €307
includes taxes & fees
9 Mar - 10 Mar
Sojourn's Harborage unit 6

Water Front Delight on the Bay

Water Front Delight on the Bay
Willoughby Spit
7.8 out of 10, Good, (25 reviews)
"Everything was very nice really enjoyed "
United States
Deborah B.
The price is €289
includes taxes & fees
28 Feb - 1 Mar
Water Front Delight on the Bay

OV Mosaic - Coconut Suite

OV Mosaic - Coconut Suite
East Ocean View
9.6 out of 10, Exceptional, (7 reviews)
"Great location. Fit our needs perfectly. Highly recommend."
United States
Wendy A.
OV Mosaic - Coconut Suite

Private 1 Bed Apt - Historic Olde Towne Portsmouth

Private 1 Bed Apt - Historic Olde Towne Portsmouth
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 €161
includes taxes & fees
7 Feb - 8 Feb
Private 1 Bed Apt - Historic Olde Towne Portsmouth
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, apart-hotels, 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 favorite 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 depends 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 €116 per night. Entering your travel dates in the search wizard you might find 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 Bryant Farms Park, 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 40 holiday rentals for your stay in Chesapeake.

What’s there to see and do in Chesapeake?

Family-friendly attractions include Bryant Farms Park and Broadmoor 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.