Chesapeake Holiday Rentals

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Check prices for these dates

In two weeks
6 Mar - 8 Mar
In two months
17 Apr - 19 Apr
In three months
15 May - 17 May
In four months
12 Jun - 14 Jun

Our top choices for Chesapeake holiday rentals

Pool

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
The price is HK$977
HK$1,304 total
includes taxes & fees
22 Feb - 23 Feb
Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Indoor pool

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
Chesapeake
The price is HK$827
HK$1,131 total
includes taxes & fees
22 Feb - 23 Feb
1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
Terrace/patio

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.
The price is HK$1,055
HK$2,110 total
includes taxes & fees
18 Feb - 19 Feb
3-bedroom home away from home in fabulous Chesapeake, Virginia.
Indoor pool

Studio | Free Breakfast. Indoor Pool & Hot Tub

Studio | Free Breakfast. Indoor Pool & Hot Tub
Chesapeake
The price is HK$827
HK$1,131 total
includes taxes & fees
22 Feb - 23 Feb
Studio | Free Breakfast. Indoor Pool & Hot Tub
Indoor pool

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.
The price is HK$1,083
HK$1,425 total
includes taxes & fees
22 Feb - 23 Feb
Great Studio | Pool & Hot Tub. Your Next Vacation
Indoor pool

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.
The price is HK$978
HK$1,304 total
includes taxes & fees
22 Feb - 23 Feb
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!
Indoor pool

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
9.0 out of 10, Wonderful, (2 reviews)
"Very clean , great location. Will stay there again!!!"
United States
Tony H.
The price is HK$1,146
HK$1,506 total
includes taxes & fees
22 Feb - 23 Feb
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!
Dining

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 HK$1,563
HK$3,139 total
includes taxes & fees
18 Feb - 19 Feb
Luxurious RV
Terrace/patio

Comfortable Beach Trailer Home

Comfortable Beach Trailer Home
Sandbridge
9.2 out of 10, Wonderful, (80 reviews)
"The stay was great. We loved walking around the neighborhood at sunset to see the view over the water. We would definitely stay here again. "
United States
Maddi S.
The price is HK$1,563
HK$3,139 total
includes taxes & fees
28 Feb - 1 Mar
Comfortable Beach Trailer Home
Interior

The Speakeasy Downtown Newport News

The Speakeasy Downtown Newport News
2.0 star property
Downtown Newport News
The price is HK$899
HK$2,193 total
includes taxes & fees
22 Feb - 23 Feb
The Speakeasy Downtown Newport News
Terrace/patio

stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
2.5 star property
Suffolk
9.4 out of 10, Exceptional, (62 reviews)
"The staff was so friendly. The rooms were so nice. I loved the kitchen and breakfast bar."
United States
Nicole
The price is HK$921
HK$1,058 total
includes taxes & fees
1 Mar - 2 Mar
stayAPT Suites Suffolk-Chesapeake
Interior

Centrally Located Hampton Roads Home w/ Game Room!

Centrally Located Hampton Roads Home w/ Game Room!
3.0 star property
Portsmouth
The price is HK$2,055
HK$4,834 total
includes taxes & fees
3 Mar - 4 Mar
Centrally Located Hampton Roads Home w/ Game Room!
On the beach, sun-loungers, beach towels

New Beach Home on the Chesapeake Bay

New Beach Home on the Chesapeake Bay
East Ocean View
8.8 out of 10, Excellent, (3 reviews)
"Excellent Host! The check in process an eaze! The house is as described super clean! The host provided more than enough accommodations and even leaves a nice treat for their guest! The location is excellent right by the stairs to the beach! Will definitely book again. "
United States
Shardae F.
The price is HK$3,510
HK$6,352 total
includes taxes & fees
18 Feb - 19 Feb
New Beach Home on the Chesapeake Bay
Interior

Comfortable & Private 2 Bedrm Cottage w/ King bed.

Comfortable & Private 2 Bedrm Cottage w/ King bed.
Portsmouth
9.8 out of 10, Exceptional, (17 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 HK$788
HK$2,287 total
includes taxes & fees
18 Feb - 19 Feb
Comfortable & Private 2 Bedrm Cottage w/ King bed.
Beach towels

Family friendly 5 bedroom home within Walking distance To CNU

Family friendly 5 bedroom home within Walking distance To CNU
Central Newport News
10.0 out of 10, Exceptional, (51 reviews)
"Was an absolute great stay! "
United States
Melanie E.
The price is HK$4,142
HK$6,190 total
includes taxes & fees
18 Feb - 19 Feb
Family friendly 5 bedroom home within Walking distance To CNU
On the beach

Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House

Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House
Willoughby Spit
9.0 out of 10, Wonderful, (69 reviews)
"Amazing little cottage right on the water. Would love to stay again. "
United States
ROBYN B.
The price is HK$1,008
HK$1,992 total
includes taxes & fees
8 Mar - 9 Mar
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House
Fridge, microwave, oven, stovetop

Old Beach House Made New for Large Accommodations

Old Beach House Made New for Large Accommodations
Norfolk
9.2 out of 10, Wonderful, (15 reviews)
"Spacious and very clean! Perfect for a big family gathering."
United States
Jennifer S.
The price is HK$1,946
HK$5,614 total
includes taxes & fees
23 Feb - 24 Feb
Old Beach House Made New for Large Accommodations
TV

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, (106 reviews)
"The rooms were very clean and be was comfortable!"
United States
CYMANDYE V.
The price is HK$781
HK$1,767 total
includes taxes & fees
18 Feb - 19 Feb
The Art Door Duplex only minutes from beach
Exterior

Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!

Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!
Coliseum Central
9.6 out of 10, Exceptional, (42 reviews)
"Another amazing stay at Jackie's place!"
United States
Sherri J.
The price is HK$2,814
HK$5,184 total
includes taxes & fees
19 Feb - 20 Feb
Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!
2 bedrooms

Ice Ice Baby Downtown Newport News

Ice Ice Baby Downtown Newport News
2.0 star property
Downtown Newport News
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 HK$725
HK$1,963 total
includes taxes & fees
18 Feb - 19 Feb
Ice Ice Baby Downtown Newport News
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

Hyatt Place Hampton Convention Center

Hyatt Place Hampton Convention Center

10/10 Excellent
"The staff was wonderful. Updated clean room. Great breakfast. Very accommodating. "
Lucia 3-night trip
Posted 1 day ago
Hyatt Place Hampton Convention Center

Find out more about Chesapeake

Search for holiday rentals in Chesapeake on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesapeake using one of the methods below:

  • View our selection of featured holiday rentals in Chesapeake
  • Use the map to find apartments and other holiday homes in the Chesapeake neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chesapeake while they last

Look no further and take a look at our great range of rental properties in Chesapeake!

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 Lake Drummond and Oak Grove Lake 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.