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Chesapeake Vacation Packages

Build your package with 2 more options

Chesapeake Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Pamlico Station Edgecamp

Pamlico Station Edgecamp

2 out of 5
Price was $674, price is now $453 per person
$453
per person
Feb 14 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Stay at this hotel in Rodanthe. Enjoy free WiFi, free parking, and a sauna. Popular attractions Rodanthe Pier and Chicamacomico Life-Saving Station Historic Site and Museum are located nearby.
Sanderling Resort Residences

Sanderling Resort Residences

4 out of 5
Save 100% on your flight
Price was $1,696, price is now $1,044 per person
$1,044
per person
Mar 29 - Apr 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Norfolk (ORF)
Book a stay at this beach resort in Kitty Hawk. Enjoy 2 outdoor pools, a full-service spa, and 2 restaurants. Popular attractions The Sanderling Spa and Nor'Banks Sailing are located nearby.
The Sanderling

The Sanderling

4 out of 5
Save 100% on your flight
Price was $1,579, price is now $1,050 per person
$1,050
per person
Mar 17 - Mar 24
found 5 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Book a stay at this beach hotel in Kitty Hawk. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions The Sanderling Spa and Nor'Banks Sailing are located nearby.
Ocean 27

Ocean 27

2.5 out of 5
Save 100% on your flight
Price was $2,457, price is now $1,689 per person
$1,689
per person
Mar 6 - Mar 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Book a stay at this beach hotel in Virginia Beach. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Virginia Beach Boardwalk and Naval Aviation Monument Park are located nearby.
The Atrium Resort, Virginia Beach by Vacatia

The Atrium Resort, Virginia Beach by Vacatia

3.5 out of 5
Save 100% on your flight
Price was $1,021, price is now $730 per person
$730
per person
Mar 31 - Apr 7
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Norfolk (ORF)
Stay at this aparthotel in Virginia Beach. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Virginia Beach Boardwalk and Pirates Paradise Mini Golf are located nearby.
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

3 out of 5
Save 100% on your flight
Price was $799, price is now $588 per person
$588
per person
Mar 17 - Mar 24
found 5 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Book a stay at this beach aparthotel in Virginia Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Virginia Beach Boardwalk and Old Coast Guard Station are located nearby.
The Ocean Key Virginia Beach Resort

The Ocean Key Virginia Beach Resort

3 out of 5
Save 100% on your flight
Price was $772, price is now $572 per person
$572
per person
Mar 17 - Mar 24
found 5 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Stay at this aparthotel in Virginia Beach. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Virginia Beach Boardwalk and Sandbridge Beach are located nearby.
The Burrus House Inn Waterfront Suites

The Burrus House Inn Waterfront Suites

3 out of 5
Save 100% on your flight
Price was $1,792, price is now $1,339 per person
$1,339
per person
Mar 17 - Mar 24
found 5 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Stay at this B&B in Manteo. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Roanoke Marshes Lighthouse and Dare County Arts Council are located nearby.

Chesapeake Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Pamlico Station Edgecamp

Pamlico Station Edgecamp

2 out of 5
South Rodanthe
Price was $704, price is now $532 per person
$532
per person
Mar 29 - Apr 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Norfolk (ORF)
Sanderling Resort Residences

Sanderling Resort Residences

4 out of 5
Save 100% on your flight
Price was $1,696, price is now $1,044 per person
$1,044
per person
Mar 29 - Apr 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Norfolk (ORF)
Ocean 27

Ocean 27

2.5 out of 5
Northeast Virginia Beach
Save 100% on your flight
Price was $2,457, price is now $1,689 per person
$1,689
per person
Mar 6 - Mar 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
The Sanderling

The Sanderling

4 out of 5
Price was $858, price is now $636 per person
$636
per person
Mar 29 - Apr 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Norfolk (ORF)

Chesapeake Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Pamlico Station Edgecamp

Pamlico Station Edgecamp

2 out of 5
South Rodanthe
Save 100% on your flight
Price was $986, price is now $591 per person
$591
per person
Feb 14 - Feb 19
found 11 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
The Sanderling

The Sanderling

4 out of 5
Save 100% on your flight
Price was $1,579, price is now $1,050 per person
$1,050
per person
Mar 17 - Mar 24
found 5 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
The Atrium Resort, Virginia Beach by Vacatia

The Atrium Resort, Virginia Beach by Vacatia

3.5 out of 5
Northeast Virginia Beach
Save 100% on your flight
Price was $1,021, price is now $730 per person
$730
per person
Mar 31 - Apr 7
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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
Northeast Virginia Beach
Save 100% on your flight
Price was $923, price is now $677 per person
$677
per person
Mar 31 - Apr 7
found 3 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Norfolk (ORF)

Top Flight Deals

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

Frontier Airlines
Sun, Jan 25 - Mon, Feb 2
ATL
Hartsfield-Jackson Atlanta Intl.
ORF
Norfolk Intl.
$90 Roundtrip, found 5 hours ago
$90
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Sun, Jan 25 from Hartsfield-Jackson Atlanta Intl. to Norfolk Intl., returning Mon, Feb 2, priced at $90 found 5 hours ago
Breeze Airways
Fri, Jan 30 - Sun, Feb 1
TPA
Tampa Intl.
ORF
Norfolk Intl.
$92 Roundtrip, found 2 days ago
$92
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Jan 30 from Tampa Intl. to Norfolk Intl., returning Sun, Feb 1, priced at $92 found 2 days ago
Spirit Airlines
Mon, Feb 23 - Sat, Feb 28
DFW
Dallas-Fort Worth Intl.
ORF
Norfolk Intl.
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Mon, Feb 23 from Dallas-Fort Worth Intl. to Norfolk Intl., returning Sat, Feb 28, priced at $137 found 1 day ago
American Airlines
Thu, Jan 22 - Thu, Jan 29
BOS
Logan Intl.
ORF
Norfolk Intl.
$159 Roundtrip, found 5 days ago
$159
Roundtrip
found 5 days ago
Select American Airlines flight, departing Thu, Jan 22 from Logan Intl. to Norfolk Intl., returning Thu, Jan 29, priced at $159 found 5 days ago