Chesapeake City County Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Our top choices for Chesapeake City County holiday rentals

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)
"Good location and spacious rooms. Good stay!"
United States
Ariel G.
The price is HK$1,420
HK$1,858 total
includes taxes & fees
3 May - 4 May
Free Breakfast. Indoor Pool & Hot Tub. Close to the Virginia Beach business district!

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, (46 reviews)
"Great place to stay, everything was as described! Would definitely stay here again. "
United States
James W.
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.
The price is HK$1,178
HK$1,553 total
includes taxes & fees
17 May - 18 May
Great Studio | Pool & Hot Tub. Your Next Vacation

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$1,375
HK$1,798 total
includes taxes & fees
4 May - 5 May
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub
Chesapeake
The price is HK$1,310
HK$1,687 total
includes taxes & fees
28 Apr - 29 Apr
1 Bedroom | Free Breakfast. Indoor Pool & Hot Tub

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$1,639
HK$2,156 total
includes taxes & fees
27 May - 28 May
Free Breakfast. Indoor Pool & Hot Tub. Near the Virginia Beach business district!

Studio | Free Breakfast. Indoor Pool & Hot Tub

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

Studio | Free Breakfast. Indoor Pool & Hot Tub.

Studio | Free Breakfast. Indoor Pool & Hot Tub.
Chesapeake
The price is HK$1,317
HK$1,695 total
includes taxes & fees
28 May - 29 May
Studio | Free Breakfast. Indoor Pool & Hot Tub.

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!

King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!
Chesapeake
The price is HK$1,310
HK$1,714 total
includes taxes & fees
3 May - 4 May
King Suite. Free Breakfast. Indoor Pool & Hot Tub. Great for Business Travelers!

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$1,567
HK$3,129 total
includes taxes & fees
28 Apr - 29 Apr
Luxurious RV

The Speakeasy Downtown Newport News

The Speakeasy Downtown Newport News
2.0 star property
Downtown Newport News
The price is HK$849
HK$2,060 total
includes taxes & fees
28 Apr - 29 Apr
The Speakeasy Downtown Newport News

stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
2.5 star property
Suffolk
9.4 out of 10, Exceptional, (74 reviews)
"perfect stay. would definitely stay again "
United States
berry
The price is HK$932
HK$1,071 total
includes taxes & fees
4 May - 5 May
stayAPT Suites Suffolk-Chesapeake

Norfolk Beach Cottage Rental

Norfolk Beach Cottage Rental
East Ocean View
9.0 out of 10, Wonderful, (283 reviews)
"Great place loved it cozy beach house "
United States
JaLiylah M.
The price is HK$1,303
HK$3,143 total
includes taxes & fees
28 Apr - 29 Apr
Norfolk Beach Cottage Rental

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
8.8 out of 10, Excellent, (73 reviews)
"We love this little quiet beach house "
United States
Annie N.
The price is HK$1,559
HK$2,763 total
includes taxes & fees
3 May - 4 May
Rustic Ocean View Beach House - BEST Location in Ocean View! 2 bed/1 bath House

Steps to the Ocean! Family and Dog Friendly North End Cottage w/ Rsrv Parking

Steps to the Ocean! Family and Dog Friendly North End Cottage w/ Rsrv Parking
Northeast Virginia Beach
9.8 out of 10, Exceptional, (263 reviews)
"Clean well taken care of property. Process to rent is easy and the owner was extremely accommodating. Thanks for a great stay"
United States
Kevin P.
Steps to the Ocean! Family and Dog Friendly North End Cottage w/ Rsrv Parking

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$2,061
HK$4,846 total
includes taxes & fees
30 Apr - 1 May
Centrally Located Hampton Roads Home w/ Game Room!

Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!

Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!
Willoughby Spit
8.8 out of 10, Excellent, (75 reviews)
"Clean well equipped for a nice getaway "
United States
Sheila H.
The price is HK$1,192
HK$2,286 total
includes taxes & fees
28 Apr - 29 Apr
Cozy Historic Beach House only Steps Away from Beach and Fishing Pier!

Wooded Wonderland

Wooded Wonderland
Portsmouth
9.8 out of 10, Exceptional, (12 reviews)
"Easy check in. House very clean and well equipped. Comfortable stay"
United States
Nona C.
The price is HK$1,939
HK$4,570 total
includes taxes & fees
28 Apr - 29 Apr
Wooded Wonderland

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$2,094
HK$4,262 total
includes taxes & fees
28 Apr - 29 Apr
Fabulous 5 Bedroom 3 Bathroom Holiday House Near Beaches. WE SANITIZE!

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, (53 reviews)
"Was an absolute great stay! "
United States
Melanie E.
The price is HK$5,132
HK$7,575 total
includes taxes & fees
29 Apr - 30 Apr
Family friendly 5 bedroom home within Walking distance To CNU
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chesapeake City County Hotel Reviews