Cheap Vacations in Chesapeake City County

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Chesapeake City County vacations

Price found within the past 48 hours. Click for updated prices.
Alamar Resort Inn

Alamar Resort Inn

2 out of 5
Northeast Virginia Beach
Price was $618, price is now $488 per person
$488
per person
Jul 4 - Jul 6
found 18 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Sea Ranch Resort

Sea Ranch Resort

3 out of 5
Price was $957, price is now $702 per person
$702
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Sea Scape Beach and Golf Villas

Sea Scape Beach and Golf Villas

3.5 out of 5
Sea Scape
Price was $1,069, price is now $813 per person
$813
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Sanderling Resort Residences

Sanderling Resort Residences

4 out of 5
Save 100% on your flight
Price was $2,900, price is now $2,230 per person
$2,230
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
TRU by Hilton Chesapeake, VA

TRU by Hilton Chesapeake, VA

2.5 out of 5
Greenbrier
Price was $663, price is now $517 per person
$517
per person
Jun 27 - Jun 30
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
The Burrus House Inn Waterfront Suites

The Burrus House Inn Waterfront Suites

3 out of 5
Price was $1,137, price is now $895 per person
$895
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Price was $1,094, price is now $865 per person
$865
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Hilton Norfolk The Main

Hilton Norfolk The Main

4 out of 5
Downtown Norfolk
Price was $1,192, price is now $951 per person
$951
per person
Jun 27 - Jun 30
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Boardwalk Resort and Villas

Boardwalk Resort and Villas

3 out of 5
Northeast Virginia Beach
Price was $813, price is now $662 per person
$662
per person
Jun 27 - Jun 30
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Outer Banks Beach Club

Outer Banks Beach Club

2.5 out of 5
Price was $937, price is now $768 per person
$768
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)

3-night Chesapeake City County vacations

Price found within the past 48 hours. Click for updated prices.
TRU by Hilton Chesapeake, VA

TRU by Hilton Chesapeake, VA

2.5 out of 5
Price was $663, price is now $517 per person
$517
per person
Jun 27 - Jun 30
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Sea Ranch Resort

Sea Ranch Resort

3 out of 5
Price was $957, price is now $702 per person
$702
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Sea Scape Beach and Golf Villas

Sea Scape Beach and Golf Villas

3.5 out of 5
Price was $1,069, price is now $813 per person
$813
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Sanderling Resort Residences

Sanderling Resort Residences

4 out of 5
Save 100% on your flight
Price was $2,900, price is now $2,230 per person
$2,230
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
The Burrus House Inn Waterfront Suites

The Burrus House Inn Waterfront Suites

3 out of 5
Price was $1,137, price is now $895 per person
$895
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Price was $1,094, price is now $865 per person
$865
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Hilton Norfolk The Main

Hilton Norfolk The Main

4 out of 5
Price was $1,192, price is now $951 per person
$951
per person
Jun 27 - Jun 30
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Boardwalk Resort and Villas

Boardwalk Resort and Villas

3 out of 5
Price was $813, price is now $662 per person
$662
per person
Jun 27 - Jun 30
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Outer Banks Beach Club

Outer Banks Beach Club

2.5 out of 5
Price was $937, price is now $768 per person
$768
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Roanoke Island Inn

Roanoke Island Inn

3.5 out of 5
Price was $1,067, price is now $881 per person
$881
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
The Sanderling

The Sanderling

4 out of 5
Price was $1,472, price is now $1,217 per person
$1,217
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Pamlico Station Edgecamp

Pamlico Station Edgecamp

2 out of 5
Price was $952, price is now $791 per person
$791
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)

5-night Chesapeake City County vacations

Price found within the past 48 hours. Click for updated prices.
La Quinta Inn by Wyndham Norfolk Virginia Beach

La Quinta Inn by Wyndham Norfolk Virginia Beach

3 out of 5
Price was $756, price is now $597 per person
$597
per person
Jul 1 - Jul 6
found 17 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Alamar Resort Inn

Alamar Resort Inn

2 out of 5
Save 100% on your flight
Price was $907, price is now $631 per person
$631
per person
Jul 1 - Jul 6
found 17 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Ocean 27

Ocean 27

2.5 out of 5
Save 100% on your flight
Price was $1,249, price is now $885 per person
$885
per person
Jul 1 - Jul 6
found 17 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Holiday Inn & Suites Virginia Beach North Beach by IHG

Holiday Inn & Suites Virginia Beach North Beach by IHG

3 out of 5
Save 100% on your flight
Price was $1,652, price is now $1,201 per person
$1,201
per person
Jul 1 - Jul 6
found 17 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Belmont Inn And Suites

Belmont Inn And Suites

2 out of 5
Price was $986, price is now $749 per person
$749
per person
Jul 1 - Jul 6
found 17 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Ramada by Wyndham Virginia Beach

Ramada by Wyndham Virginia Beach

3 out of 5
Price was $973, price is now $779 per person
$779
per person
Jul 1 - Jul 6
found 17 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Boardwalk Resort and Villas

Boardwalk Resort and Villas

3 out of 5
Save 100% on your flight
Price was $1,516, price is now $1,213 per person
$1,213
per person
Jul 1 - Jul 6
found 17 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Travelodge by Wyndham Virginia Beach Bay Beach

Travelodge by Wyndham Virginia Beach Bay Beach

2 out of 5
Price was $868, price is now $701 per person
$701
per person
Jul 1 - Jul 6
found 17 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Breakers Resort Inn

Breakers Resort Inn

2 out of 5
Price was $1,295, price is now $1,054 per person
$1,054
per person
Jul 1 - Jul 6
found 17 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
The Sitio

The Sitio

2 out of 5
Save 100% on your flight
Price was $2,131, price is now $1,752 per person
$1,752
per person
Jul 1 - Jul 6
found 17 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Ramada Plaza by Wyndham Virginia Beach Oceanfront

Ramada Plaza by Wyndham Virginia Beach Oceanfront

3 out of 5
Price was $1,180, price is now $971 per person
$971
per person
Jul 1 - Jul 6
found 17 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Oceans 24

Oceans 24

2 out of 5
Save 100% on your flight
Price was $1,890, price is now $1,557 per person
$1,557
per person
Jul 1 - Jul 6
found 17 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)

6-7 night Chesapeake City County vacations

Price found within the past 48 hours. Click for updated prices.
Motel 6 Norfolk, VA – East Little Creek

Motel 6 Norfolk, VA – East Little Creek

2 out of 5
Price was $626, price is now $561 per person
$561
per person
Jul 5 - Jul 12
found 18 hours ago
Roundtrip flight included
Jacksonville (JAX) to Norfolk (ORF)
Norfolk Waterside Marriott

Norfolk Waterside Marriott

3.5 out of 5
Price was $891, price is now $785 per person
$785
per person
Jul 5 - Jul 12
found 18 hours ago
Roundtrip flight included
Jacksonville (JAX) to Norfolk (ORF)
Residence Inn Norfolk Downtown

Residence Inn Norfolk Downtown

3 out of 5
Price was $766, price is now $708 per person
$708
per person
Jul 5 - Jul 12
found 18 hours ago
Roundtrip flight included
Jacksonville (JAX) to Norfolk (ORF)

Top places to visit in Chesapeake City County

Colorful sunset over riverside resort in Cambridge Maryland USA
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Chesapeake

Chesapeake

Flight deals to Chesapeake City County

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Thu, Jul 23 - Sun, Jul 26
ATL
Atlanta
ORF
Norfolk
$56 Roundtrip, found 6 days ago
$56
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Jul 23 from Atlanta to Norfolk, returning Sun, Jul 26, priced at $56 found 6 days ago
Mon, Aug 24 - Fri, Aug 28
JAX
Jacksonville
ORF
Norfolk
$102 Roundtrip, found 1 day ago
$102
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Mon, Aug 24 from Jacksonville to Norfolk, returning Fri, Aug 28, priced at $102 found 1 day ago
Tue, Jul 21 - Wed, Jul 22
MCO
Orlando
ORF
Norfolk
$112 Roundtrip, found 4 days ago
$112
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Tue, Jul 21 from Orlando to Norfolk, returning Wed, Jul 22, priced at $112 found 4 days ago

Top rated hotels for your Chesapeake City County vacation

Wingate by Wyndham Chesapeake

Wingate by Wyndham Chesapeake

3 out of 5
817 Greenbrier Circle Chesapeake VA
Free Cancellation
Reserve now, pay when you stay
8.79 mi from city center
$93 nightly
The price is $109 total per night
$109 total
May 31 - Jun 1
Total with taxes and fees
When you stay at Wingate by Wyndham Chesapeake in Chesapeake, you'll be in the business district, within a 15-minute drive of Greenbrier Mall and Waterside District.
Pool
Hot Tub
Wyndham Virginia Beach Oceanfront

Wyndham Virginia Beach Oceanfront

3 out of 5
5700 Atlantic Ave Virginia Beach VA
Free Cancellation
Reserve now, pay when you stay
22.5 mi from city center
$104 nightly
The price is $121 total per night
$121 total
May 31 - Jun 1
Total with taxes and fees
With a stay at Wyndham Virginia Beach Oceanfront in Virginia Beach (Northeast Virginia Beach), you'll be within a 5-minute drive of Virginia Beach Boardwalk and First Landing State Park.
Pool
Pet friendly
Hyatt Place Virginia Beach / Oceanfront

Hyatt Place Virginia Beach / Oceanfront

3 out of 5
3601 ATLANTIC AVENUE Virginia Beach VA
Free Cancellation
Reserve now, pay when you stay
22.04 mi from city center
$169 nightly
The price is $196 total per night
$196 total
May 31 - Jun 1
Total with taxes and fees
With a stay at Hyatt Place Virginia Beach / Oceanfront in Virginia Beach (Northeast Virginia Beach), you'll be steps from Virginia Beach Boardwalk and Pacific Avenue.
Pool
Breakfast included
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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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.