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.
The Capes Hotel

The Capes Hotel

3 out of 5
Northeast Virginia Beach
Price was $570, price is now $497 per person
$497
per person
Nov 28 - Dec 2
found 3 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Boardwalk Resort and Villas

Boardwalk Resort and Villas

3 out of 5
Northeast Virginia Beach
Price was $901, price is now $777 per person
$777
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Sea Ranch Resort

Sea Ranch Resort

3 out of 5
Price was $590, price is now $521 per person
$521
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Holiday Inn Express Hotel & Suites Norfolk Airport by IHG

Holiday Inn Express Hotel & Suites Norfolk Airport by IHG

2.5 out of 5
Price was $924, price is now $816 per person
$816
per person
Dec 6 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
The Founders Inn and Spa, Tapestry Collection by Hilton

The Founders Inn and Spa, Tapestry Collection by Hilton

4 out of 5
Price was $797, price is now $705 per person
$705
per person
Dec 6 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Sandcastle Resort On The Beach

Sandcastle Resort On The Beach

3 out of 5
Northeast Virginia Beach
Price was $902, price is now $801 per person
$801
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

4 out of 5
Northeast Virginia Beach
Price was $692, price is now $617 per person
$617
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
The Barclay Towers Resort Hotel

The Barclay Towers Resort Hotel

2.5 out of 5
Northeast Virginia Beach
Price was $658, price is now $587 per person
$587
per person
Nov 28 - Dec 2
found 2 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
The Colony at Virginia Beach

The Colony at Virginia Beach

3 out of 5
Northeast Virginia Beach
Price was $796, price is now $712 per person
$712
per person
Nov 28 - Dec 2
found 2 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Hilton Garden Inn Virginia Beach Town Center

Hilton Garden Inn Virginia Beach Town Center

3 out of 5
Northwest
Price was $788, price is now $709 per person
$709
per person
Dec 6 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)

3-night Chesapeake City County vacations

Price found within the past 48 hours. Click for updated prices.
Sandcastle Resort On The Beach

Sandcastle Resort On The Beach

3 out of 5
Price was $500, price is now $476 per person
$476
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Midland (MAF) to Norfolk (ORF)
The Barclay Towers Resort Hotel

The Barclay Towers Resort Hotel

2.5 out of 5
Price was $605, price is now $521 per person
$521
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Midland (MAF) 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
Price was $535, price is now $497 per person
$497
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Midland (MAF) to Norfolk (ORF)
The Founders Inn and Spa, Tapestry Collection by Hilton

The Founders Inn and Spa, Tapestry Collection by Hilton

4 out of 5
Price was $562, price is now $528 per person
$528
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Midland (MAF) to Norfolk (ORF)
SpringHill Suites by Marriott Virginia Beach Oceanfront

SpringHill Suites by Marriott Virginia Beach Oceanfront

3 out of 5
Price was $648, price is now $611 per person
$611
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Midland (MAF) to Norfolk (ORF)
Hilton Garden Inn Virginia Beach Town Center

Hilton Garden Inn Virginia Beach Town Center

3 out of 5
Price was $546, price is now $518 per person
$518
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Midland (MAF) to Norfolk (ORF)
Crowne Plaza Virginia Beach Town Center by IHG

Crowne Plaza Virginia Beach Town Center by IHG

3.5 out of 5
Price was $530, price is now $504 per person
$504
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Midland (MAF) to Norfolk (ORF)
Coastal Hotel and Suites Virginia Beach Oceanfront

Coastal Hotel and Suites Virginia Beach Oceanfront

2.5 out of 5
Price was $628, price is now $600 per person
$600
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Midland (MAF) to Norfolk (ORF)
Courtyard by Marriott Norfolk Downtown

Courtyard by Marriott Norfolk Downtown

3 out of 5
Price was $543, price is now $520 per person
$520
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Midland (MAF) to Norfolk (ORF)
The Oceanfront Inn

The Oceanfront Inn

2.5 out of 5
Price was $544, price is now $525 per person
$525
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Midland (MAF) to Norfolk (ORF)
TRU by Hilton Chesapeake, VA

TRU by Hilton Chesapeake, VA

2.5 out of 5
Price was $511, price is now $495 per person
$495
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Midland (MAF) to Norfolk (ORF)
Comfort Suites Chesapeake - Norfolk

Comfort Suites Chesapeake - Norfolk

2.5 out of 5
Price was $510, price is now $495 per person
$495
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Midland (MAF) to Norfolk (ORF)

4-night Chesapeake City County vacations

Price found within the past 48 hours. Click for updated prices.
The Capes Hotel

The Capes Hotel

3 out of 5
Price was $570, price is now $497 per person
$497
per person
Nov 28 - Dec 2
found 3 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

4 out of 5
Price was $1,024, price is now $881 per person
$881
per person
Nov 25 - Nov 29
found 1 day 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 $901, price is now $777 per person
$777
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Sandcastle Resort On The Beach

Sandcastle Resort On The Beach

3 out of 5
Price was $902, price is now $801 per person
$801
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
The Barclay Towers Resort Hotel

The Barclay Towers Resort Hotel

2.5 out of 5
Price was $658, price is now $587 per person
$587
per person
Nov 28 - Dec 2
found 2 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
The Colony at Virginia Beach

The Colony at Virginia Beach

3 out of 5
Price was $796, price is now $712 per person
$712
per person
Nov 28 - Dec 2
found 2 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
Price was $883, price is now $814 per person
$814
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Residence Inn by Marriott Norfolk Airport

Residence Inn by Marriott Norfolk Airport

3 out of 5
Price was $979, price is now $905 per person
$905
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Holiday Inn Express Hotel & Suites Norfolk Airport by IHG

Holiday Inn Express Hotel & Suites Norfolk Airport by IHG

2.5 out of 5
Price was $1,002, price is now $927 per person
$927
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Wyndham Virginia Beach Oceanfront

Wyndham Virginia Beach Oceanfront

3 out of 5
Price was $555, price is now $514 per person
$514
per person
Nov 28 - Dec 2
found 3 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Comfort Inn & Suites Hampton near Coliseum

Comfort Inn & Suites Hampton near Coliseum

3 out of 5
Price was $900, price is now $839 per person
$839
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
SpringHill Suites by Marriott Virginia Beach Oceanfront

SpringHill Suites by Marriott Virginia Beach Oceanfront

3 out of 5
Price was $1,021, price is now $958 per person
$958
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)

5-night Chesapeake City County vacations

Price found within the past 48 hours. Click for updated prices.
Budget Inn Norfolk Va

Budget Inn Norfolk Va

2 out of 5
Price was $542, price is now $507 per person
$507
per person
Nov 25 - Nov 30
found 22 hours ago
Roundtrip flight included
New York (NYC) to Norfolk (ORF)
La Quinta Inn & Suites by Wyndham Norfolk

La Quinta Inn & Suites by Wyndham Norfolk

3 out of 5
Price was $758, price is now $685 per person
$685
per person
Nov 25 - Nov 30
found 22 hours ago
Roundtrip flight included
New York (NYC) to Norfolk (ORF)
Residence Inn by Marriott Norfolk Airport

Residence Inn by Marriott Norfolk Airport

3 out of 5
Price was $790, price is now $715 per person
$715
per person
Nov 25 - Nov 30
found 22 hours ago
Roundtrip flight included
New York (NYC) to Norfolk (ORF)
Wyndham Garden Norfolk Downtown

Wyndham Garden Norfolk Downtown

3.5 out of 5
Price was $745, price is now $675 per person
$675
per person
Nov 25 - Nov 30
found 22 hours ago
Roundtrip flight included
New York (NYC) to Norfolk (ORF)
The Inn at Four Eleven York

The Inn at Four Eleven York

4 out of 5
Price was $1,325, price is now $1,233 per person
$1,233
per person
Nov 25 - Nov 30
found 22 hours ago
Roundtrip flight included
New York (NYC) to Norfolk (ORF)
Sleep Inn Lake Wright - Norfolk Airport

Sleep Inn Lake Wright - Norfolk Airport

2.5 out of 5
Price was $653, price is now $612 per person
$612
per person
Nov 25 - Nov 30
found 22 hours ago
Roundtrip flight included
New York (NYC) to Norfolk (ORF)
Quality Suites Lake Wright - Norfolk Airport

Quality Suites Lake Wright - Norfolk Airport

3 out of 5
Price was $648, price is now $608 per person
$608
per person
Nov 25 - Nov 30
found 22 hours ago
Roundtrip flight included
New York (NYC) to Norfolk (ORF)
Spark by Hilton Norfolk

Spark by Hilton Norfolk

3 out of 5
Price was $645, price is now $617 per person
$617
per person
Nov 25 - Nov 30
found 22 hours ago
Roundtrip flight included
New York (NYC) to Norfolk (ORF)
Econo Lodge Little Creek

Econo Lodge Little Creek

2 out of 5
Price was $628, price is now $603 per person
$603
per person
Nov 25 - Nov 30
found 22 hours ago
Roundtrip flight included
New York (NYC) to Norfolk (ORF)
Ocean View Inn

Ocean View Inn

2 out of 5
Price was $596, price is now $573 per person
$573
per person
Nov 25 - Nov 30
found 22 hours ago
Roundtrip flight included
New York (NYC) to Norfolk (ORF)
Holiday Inn Express Hotel & Suites Norfolk Airport by IHG

Holiday Inn Express Hotel & Suites Norfolk Airport by IHG

2.5 out of 5
Price was $846, price is now $816 per person
$816
per person
Nov 25 - Nov 30
found 22 hours ago
Roundtrip flight included
New York (NYC) to Norfolk (ORF)
Econo Lodge Norfolk Airport

Econo Lodge Norfolk Airport

2 out of 5
Price was $633, price is now $614 per person
$614
per person
Nov 25 - Nov 30
found 22 hours ago
Roundtrip flight included
New York (NYC) to Norfolk (ORF)

6-7 night Chesapeake City County vacations

Price found within the past 48 hours. Click for updated prices.
Budget Inn Norfolk Va

Budget Inn Norfolk Va

2 out of 5
Price was $427, price is now $390 per person
$390
per person
Dec 13 - Dec 19
found 2 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Norfolk (ORF)
Wyndham Garden Norfolk Downtown

Wyndham Garden Norfolk Downtown

3.5 out of 5
Price was $641, price is now $570 per person
$570
per person
Dec 13 - Dec 19
found 2 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Norfolk (ORF)
Sleep Inn Lake Wright - Norfolk Airport

Sleep Inn Lake Wright - Norfolk Airport

2.5 out of 5
Price was $507, price is now $477 per person
$477
per person
Dec 13 - Dec 19
found 2 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Norfolk (ORF)
Quality Suites Lake Wright - Norfolk Airport

Quality Suites Lake Wright - Norfolk Airport

3 out of 5
Price was $504, price is now $475 per person
$475
per person
Dec 13 - Dec 19
found 2 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to Norfolk (ORF)
The Inn at Four Eleven York

The Inn at Four Eleven York

4 out of 5
Price was $1,504, price is now $1,252 per person
$1,252
per person
Dec 6 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Crowne Plaza Virginia Beach Town Center by IHG

Crowne Plaza Virginia Beach Town Center by IHG

3.5 out of 5
Price was $717, price is now $626 per person
$626
per person
Dec 6 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
La Quinta Inn & Suites by Wyndham Norfolk

La Quinta Inn & Suites by Wyndham Norfolk

3 out of 5
Price was $758, price is now $662 per person
$662
per person
Dec 6 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Holiday Inn Express Hotel & Suites Norfolk Airport by IHG

Holiday Inn Express Hotel & Suites Norfolk Airport by IHG

2.5 out of 5
Price was $924, price is now $816 per person
$816
per person
Dec 6 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
The Founders Inn and Spa, Tapestry Collection by Hilton

The Founders Inn and Spa, Tapestry Collection by Hilton

4 out of 5
Price was $797, price is now $705 per person
$705
per person
Dec 6 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Hilton Garden Inn Virginia Beach Town Center

Hilton Garden Inn Virginia Beach Town Center

3 out of 5
Price was $788, price is now $709 per person
$709
per person
Dec 6 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Econo Lodge Little Creek

Econo Lodge Little Creek

2 out of 5
Price was $651, price is now $586 per person
$586
per person
Dec 6 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Residence Inn by Marriott Norfolk Airport

Residence Inn by Marriott Norfolk Airport

3 out of 5
Price was $812, price is now $732 per person
$732
per person
Dec 6 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)

Top places to visit in Chesapeake City County

A golf course, a large building complex, and a marina by a river.
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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.

Sat, Dec 5 - Sun, Dec 6
MCO
Orlando
ORF
Norfolk
$118 Roundtrip, found 5 hours ago
$118
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Sat, Dec 5 from Orlando to Norfolk, returning Sun, Dec 6, priced at $118 found 5 hours ago
Fri, Dec 4 - Sun, Dec 6
ATL
Atlanta
ORF
Norfolk
$149 Roundtrip, found 6 days ago
$149
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Fri, Dec 4 from Atlanta to Norfolk, returning Sun, Dec 6, priced at $149 found 6 days ago
Sat, Nov 7 - Mon, Nov 9
TPA
Tampa
ORF
Norfolk
$167 Roundtrip, found 2 days ago
$167
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, Nov 7 from Tampa to Norfolk, returning Mon, Nov 9, priced at $167 found 2 days ago

Top rated hotels for your Chesapeake City County vacation

Comfort Suites Chesapeake - Norfolk

Comfort Suites Chesapeake - Norfolk

2.5 out of 5
1550 Crossways Blvd Chesapeake VA
Free Cancellation
7.97 mi from city center
$84 nightly
The price is $99 total per night
$99 total
Nov 22 - Nov 23
Total with taxes and fees
A stay at Comfort Suites Chesapeake - Norfolk places you in the heart of Chesapeake, a 2-minute drive from Greenbrier Mall and 11 minutes from Norfolk Premium Outlets.
Pool
Breakfast included
YourSpace Hotels Chesapeake

YourSpace Hotels Chesapeake

3 out of 5
2137 Starmount Parkway Chesapeake VA
12.46 mi from city center
$98 nightly
The price is $115 total per night
$115 total
Nov 15 - Nov 16
Total with taxes and fees
With a stay at YourSpace Hotels Chesapeake in Chesapeake (Western Branch North), you'll be within a 5-minute drive of Western Branch Park Dog Park and Chesapeake Square Mall.
Pet friendly
Parking included
Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

3 out of 5
1101 Atlantic Ave Virginia Beach VA
21.42 mi from city center
Get rates
Located in Virginia Beach (Northeast Virginia Beach), Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel is steps from Virginia Beach Boardwalk and a 4-minute drive from Virginia Beach Convention Center.
Pool
Parking 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.