Cheap Vacations in Chesapeake City County

Choose two or more items and save on your trip:

Chesapeake City County vacations

Price found within the past 48 hours. Click for updated prices.
Travelodge by Wyndham Norfolk Airport

Travelodge by Wyndham Norfolk Airport

2 out of 5
Price was $489, price is now $470 per person
$470
per person
Nov 19 - Nov 22
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
The Colony at Virginia Beach

The Colony at Virginia Beach

3 out of 5
Northeast Virginia Beach
Price was $1,049, price is now $846 per person
$846
per person
Nov 21 - Nov 27
found 9 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Fairfield Inn & Suites by Marriott Virginia Beach Oceanfront

Fairfield Inn & Suites by Marriott Virginia Beach Oceanfront

3 out of 5
Northeast Virginia Beach
Price was $802, price is now $688 per person
$688
per person
Nov 21 - Nov 27
found 9 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Comfort Suites Beachfront

Comfort Suites Beachfront

2.5 out of 5
Northeast Virginia Beach
Price was $703, price is now $633 per person
$633
per person
Nov 21 - Nov 27
found 9 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Embassy Suites by Hilton Virginia Beach Oceanfront Resort

Embassy Suites by Hilton Virginia Beach Oceanfront Resort

3.5 out of 5
Northeast Virginia Beach
Price was $1,052, price is now $974 per person
$974
per person
Nov 21 - Nov 27
found 9 hours 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 $977, price is now $907 per person
$907
per person
Nov 21 - Nov 28
found 10 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Norfolk (ORF)
Comfort Inn & Suites Hampton near Coliseum

Comfort Inn & Suites Hampton near Coliseum

3 out of 5
Coliseum Central
Price was $766, price is now $722 per person
$722
per person
Nov 21 - Nov 28
found 10 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Norfolk (ORF)
The Sitio

The Sitio

4 out of 5
Northeast Virginia Beach
Price was $1,016, price is now $966 per person
$966
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Norfolk (ORF)
Holiday Inn Express & Suites VA Beach Oceanfront by IHG

Holiday Inn Express & Suites VA Beach Oceanfront by IHG

3.5 out of 5
Northeast Virginia Beach
Price was $808, price is now $770 per person
$770
per person
Nov 21 - Nov 28
found 10 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Norfolk (ORF)
Hilton Garden Inn Virginia Beach Town Center

Hilton Garden Inn Virginia Beach Town Center

3 out of 5
Northwest
Price was $633, price is now $605 per person
$605
per person
Nov 25 - Nov 28
found 13 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Norfolk (ORF)

3-night Chesapeake City County vacations

Price found within the past 48 hours. Click for updated prices.
Econo Lodge Norfolk Airport

Econo Lodge Norfolk Airport

2 out of 5
Price was $554, price is now $544 per person
$544
per person
Nov 25 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Norfolk (ORF)
Boardwalk Resort and Villas

Boardwalk Resort and Villas

3 out of 5
Price was $673, price is now $587 per person
$587
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Norfolk (ORF)
The Barclay Towers Resort Hotel

The Barclay Towers Resort Hotel

2.5 out of 5
Price was $748, price is now $661 per person
$661
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Norfolk (ORF)
The Colony at Virginia Beach

The Colony at Virginia Beach

3 out of 5
Price was $922, price is now $818 per person
$818
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) 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 $769, price is now $689 per person
$689
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Norfolk (ORF)
The Capes Hotel

The Capes Hotel

3 out of 5
Price was $675, price is now $619 per person
$619
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) 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 $670, price is now $633 per person
$633
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) 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 $650, price is now $617 per person
$617
per person
Nov 25 - Nov 28
found 13 hours ago
Roundtrip non-stop flight included
Phoenix (PHX) to Norfolk (ORF)
The Sitio

The Sitio

4 out of 5
Price was $1,016, price is now $966 per person
$966
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Norfolk (ORF)
Wyndham Virginia Beach Oceanfront

Wyndham Virginia Beach Oceanfront

3 out of 5
Price was $634, price is now $603 per person
$603
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Norfolk (ORF)
SpringHill Suites by Marriott Virginia Beach Oceanfront

SpringHill Suites by Marriott Virginia Beach Oceanfront

3 out of 5
Price was $768, price is now $731 per person
$731
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) 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 $662, price is now $632 per person
$632
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Norfolk (ORF)

4-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 $466, price is now $441 per person
$441
per person
Nov 26 - Nov 30
found 15 hours ago
Roundtrip 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 $652, price is now $594 per person
$594
per person
Nov 26 - Nov 30
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Wyndham Garden Norfolk Downtown

Wyndham Garden Norfolk Downtown

3.5 out of 5
Price was $646, price is now $589 per person
$589
per person
Nov 26 - Nov 30
found 15 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 $585, price is now $542 per person
$542
per person
Nov 26 - Nov 30
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Travelodge by Wyndham Norfolk Airport

Travelodge by Wyndham Norfolk Airport

2 out of 5
Price was $517, price is now $490 per person
$490
per person
Nov 26 - Nov 30
found 15 hours ago
Roundtrip 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 $564, price is now $536 per person
$536
per person
Nov 26 - Nov 30
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Quality Suites Lake Wright - Norfolk Airport

Quality Suites Lake Wright - Norfolk Airport

3 out of 5
Price was $564, price is now $537 per person
$537
per person
Nov 26 - Nov 30
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Sleep Inn Lake Wright - Norfolk Airport

Sleep Inn Lake Wright - Norfolk Airport

2.5 out of 5
Price was $560, price is now $533 per person
$533
per person
Nov 26 - Nov 30
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
The Inn at Four Eleven York

The Inn at Four Eleven York

4 out of 5
Price was $962, price is now $922 per person
$922
per person
Dec 10 - Dec 14
found 21 hours ago
Roundtrip flight included
Phoenix (PHX) to Norfolk (ORF)
Spark by Hilton Norfolk

Spark by Hilton Norfolk

3 out of 5
Price was $581, price is now $557 per person
$557
per person
Nov 26 - Nov 30
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Ocean View Inn

Ocean View Inn

2 out of 5
Price was $512, price is now $495 per person
$495
per person
Nov 26 - Nov 30
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Econo Lodge Little Creek

Econo Lodge Little Creek

2 out of 5
Price was $537, price is now $520 per person
$520
per person
Nov 26 - Nov 30
found 15 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.
Howard Johnson by Wyndham Virginia Beach

Howard Johnson by Wyndham Virginia Beach

2.5 out of 5
Price was $544, price is now $484 per person
$484
per person
Nov 21 - Nov 27
found 9 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 $927, price is now $682 per person
$682
per person
Nov 21 - Nov 28
found 10 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Norfolk (ORF)
Boardwalk Resort and Villas

Boardwalk Resort and Villas

3 out of 5
Price was $780, price is now $591 per person
$591
per person
Nov 21 - Nov 28
found 10 hours ago
Roundtrip non-stop flight included
Hartford (BDL) 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 $855, price is now $662 per person
$662
per person
Nov 21 - Nov 27
found 9 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
The Barclay Towers Resort Hotel

The Barclay Towers Resort Hotel

2.5 out of 5
Price was $764, price is now $597 per person
$597
per person
Nov 21 - Nov 27
found 9 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 $1,049, price is now $846 per person
$846
per person
Nov 21 - Nov 27
found 9 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Sandcastle Resort On The Beach

Sandcastle Resort On The Beach

3 out of 5
Price was $648, price is now $526 per person
$526
per person
Nov 21 - Nov 27
found 9 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
The Capes Hotel

The Capes Hotel

3 out of 5
Price was $655, price is now $553 per person
$553
per person
Nov 21 - Nov 27
found 9 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Fairfield Inn & Suites by Marriott Virginia Beach Oceanfront

Fairfield Inn & Suites by Marriott Virginia Beach Oceanfront

3 out of 5
Price was $802, price is now $688 per person
$688
per person
Nov 21 - Nov 27
found 9 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
La Quinta Inn & Suites by Wyndham Virginia Beach

La Quinta Inn & Suites by Wyndham Virginia Beach

3 out of 5
Price was $636, price is now $556 per person
$556
per person
Nov 21 - Nov 27
found 9 hours ago
Roundtrip 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 $902, price is now $799 per person
$799
per person
Nov 21 - Nov 28
found 10 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Norfolk (ORF)
Days Inn by Wyndham Virginia Beach At The Beach

Days Inn by Wyndham Virginia Beach At The Beach

2 out of 5
Price was $600, price is now $534 per person
$534
per person
Nov 21 - Nov 27
found 9 hours ago
Roundtrip 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.
FlightsFlightsHotelsHotels

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, Nov 5 - Mon, Nov 9
MCO
Orlando
ORF
Norfolk
$123 Roundtrip, found 1 day ago
$123
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Nov 5 from Orlando to Norfolk, returning Mon, Nov 9, priced at $123 found 1 day ago
Sat, Nov 7 - Mon, Nov 9
TPA
Tampa
ORF
Norfolk
$147 Roundtrip, found 2 days ago
$147
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, Nov 7 from Tampa to Norfolk, returning Mon, Nov 9, priced at $147 found 2 days ago
Fri, Dec 4 - Sun, Dec 6
ATL
Atlanta
ORF
Norfolk
$149 Roundtrip, found 1 day ago
$149
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Dec 4 from Atlanta to Norfolk, returning Sun, Dec 6, priced at $149 found 1 day 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 18 - Nov 19
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
Free Cancellation
Reserve now, pay when you stay
12.46 mi from city center
$98 nightly
The price is $115 total per night
$115 total
Nov 8 - Nov 9
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 Chesapeake Square Mall and Cinemark Chesapeake Square.
Pet friendly
Parking included
Hilton Vacation Club Ocean Beach Club Virginia Beach

Hilton Vacation Club Ocean Beach Club Virginia Beach

3.5 out of 5
3401 Atlantic Ave Virginia Beach VA
Free Cancellation
Reserve now, pay when you stay
21.98 mi from city center
$96 nightly
The price is $113 total per night
$113 total
Oct 26 - Oct 27
Total with taxes and fees
Located in Virginia Beach (Northeast Virginia Beach), Hilton Vacation Club Ocean Beach Club Virginia Beach is steps from Virginia Beach Boardwalk and a 4-minute drive from First Landing State Park.
Pool
Free WiFi
Don't see what you're looking for?
See all available properties in Chesapeake City County
View all properties
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.