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Chesapeake Vacation Packages

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Chesapeake Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Sea Ranch Resort

Sea Ranch Resort

3 out of 5
Price was $500, price is now $357 per person
$357
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Stay at this 3-star beach hotel in Kill Devil Hills. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Professor Hacker's Lost Treasure Golf and Avalon Fishing Pier are located nearby.
Boardwalk Resort and Villas

Boardwalk Resort and Villas

3 out of 5
Save 100% on your flight
Price was $663, price is now $424 per person
$424
per person
Nov 8 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Stay at this 3-star beach hotel 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 Ocean Breeze Waterpark are located nearby.
John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Save 100% on your flight
Price was $629, price is now $420 per person
$420
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Book a stay at this beach hotel in Kill Devil Hills. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Destination Fun and OBX Laser Tag are located nearby.
The Lodge at Kiln Creek Resort

The Lodge at Kiln Creek Resort

3.5 out of 5
Price was $525, price is now $391 per person
$391
per person
Nov 28 - Dec 2
found 9 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Stay at this 3.5-star golf hotel in Newport News. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Patrick Henry Mall and Hampton Roads Iceplex 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 $829, price is now $630 per person
$630
per person
Nov 8 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Stay at this 3-star 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 Ocean Breeze Waterpark are located nearby.
The Colony at Virginia Beach

The Colony at Virginia Beach

2.5 out of 5
Save 100% on your flight
Price was $670, price is now $515 per person
$515
per person
Oct 18 - Oct 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Book a stay at this beach condo in Virginia Beach. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Virginia Beach Boardwalk and Sandbridge Beach are located nearby.
Hampton Inn & Suites Newport News (Oyster Point)

Hampton Inn & Suites Newport News (Oyster Point)

2.5 out of 5
Price was $512, price is now $395 per person
$395
per person
Nov 28 - Dec 2
found 9 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Book a stay at this business-friendly hotel in Newport News. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Patrick Henry Mall and Regal Kiln Creek are located nearby.
Four Sails Resort

Four Sails Resort

3.5 out of 5
Price was $523, price is now $407 per person
$407
per person
Oct 18 - Oct 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Stay at this 3.5-star beach condo in Virginia Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Virginia Beach Boardwalk and Ocean Breeze Waterpark are located nearby.

Chesapeake Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Boardwalk Resort and Villas

Boardwalk Resort and Villas

3 out of 5
Northeast Virginia Beach
Price was $457, price is now $317 per person
$317
per person
Oct 18 - Oct 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Beach Quarters Resort

Beach Quarters Resort

2.5 out of 5
Northeast Virginia Beach
Price was $469, price is now $324 per person
$324
per person
Oct 18 - Oct 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
The Lodge at Kiln Creek Resort

The Lodge at Kiln Creek Resort

3.5 out of 5
Central Newport News
Price was $525, price is now $391 per person
$391
per person
Nov 28 - Dec 2
found 9 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
The Colony at Virginia Beach

The Colony at Virginia Beach

2.5 out of 5
Northeast Virginia Beach
Save 100% on your flight
Price was $670, price is now $515 per person
$515
per person
Oct 18 - Oct 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)

Chesapeake Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Sea Ranch Resort

Sea Ranch Resort

3 out of 5
Price was $500, price is now $357 per person
$357
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Beach Quarters Resort

Beach Quarters Resort

2.5 out of 5
Northeast Virginia Beach
Save 100% on your flight
Price was $685, price is now $435 per person
$435
per person
Nov 8 - Nov 15
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
Northeast Virginia Beach
Save 100% on your flight
Price was $663, price is now $424 per person
$424
per person
Nov 8 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Save 100% on your flight
Price was $629, price is now $420 per person
$420
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)

Top Flight Deals

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

Breeze Airways
Fri, Oct 17 - Sun, Oct 19
MCO
Orlando Intl.
ORF
Norfolk Intl.
$101 Roundtrip, found 3 days ago
$101
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, Oct 17 from Orlando Intl. to Norfolk Intl., returning Sun, Oct 19, priced at $101 found 3 days ago
Spirit Airlines
Thu, Oct 16 - Sat, Oct 18
TPA
Tampa Intl.
ORF
Norfolk Intl.
$116 Roundtrip, found 1 day ago
$116
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Thu, Oct 16 from Tampa Intl. to Norfolk Intl., returning Sat, Oct 18, priced at $116 found 1 day ago
Breeze Airways
Wed, Oct 1 - Mon, Oct 6
JAX
Jacksonville Intl.
ORF
Norfolk Intl.
$122 Roundtrip, found 4 days ago
$122
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Wed, Oct 1 from Jacksonville Intl. to Norfolk Intl., returning Mon, Oct 6, priced at $122 found 4 days ago
Frontier Airlines
Fri, Sep 26 - Mon, Sep 29
ATL
Hartsfield-Jackson Atlanta Intl.
ORF
Norfolk Intl.
$136 Roundtrip, found 2 hours ago
$136
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Fri, Sep 26 from Hartsfield-Jackson Atlanta Intl. to Norfolk Intl., returning Mon, Sep 29, priced at $136 found 2 hours ago