Search Deals onChesapeake Vacation Packages
Chesapeake Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Boardwalk Resort and Villas
Price was $430, price is now $298 per person
$298
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip 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.
Sanderling Resort Residences
Save 100% on your flight
Price was $3,205, price is now $1,952 per person
$1,952
per person
Nov 8 - Nov 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Stay at this 4-star 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.
John Yancey Oceanfront Inn
Save 100% on your flight
Price was $612, price is now $399 per person
$399
per person
Oct 16 - Oct 19
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.
Beach Quarters Resort
Price was $475, price is now $325 per person
$325
per person
Oct 31 - Nov 3
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, an outdoor pool, and a beach locale. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Virginia Beach Boardwalk and Sandbridge Beach are located nearby.
Sea Ranch Resort
Price was $431, price is now $313 per person
$313
per person
Oct 16 - Oct 19
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.
Four Sails Resort
Price was $571, price is now $414 per person
$414
per person
Oct 13 - Oct 17
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.
The Sanderling
Save 100% on your flight
Price was $2,024, price is now $1,483 per person
$1,483
per person
Oct 11 - Oct 18
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Stay at this 4-star 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.
The Inn at Four Eleven York
Save 100% on your flight
Price was $950, price is now $710 per person
$710
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Stay at this 4-star B&B in Norfolk. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Waterside District and Pagoda and Oriental Garden are located nearby.
Chesapeake Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Chesapeake Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Thu, Oct 23 - Sun, Oct 26
MCO
Orlando Intl.
ORF
Norfolk Intl.
$88 Roundtrip, found 6 days ago
$88
Roundtrip
found 6 days ago
Fri, Sep 26 - Mon, Sep 29
JAX
Jacksonville Intl.
ORF
Norfolk Intl.
$103 Roundtrip, found 1 day ago
$103
Roundtrip
found 1 day ago
Mon, Aug 25 - Fri, Sep 5
TPA
Tampa Intl.
ORF
Norfolk Intl.
$114 Roundtrip, found 1 day ago
$114
Roundtrip
found 1 day ago
Fri, Nov 7 - Sun, Nov 9
ATL
Hartsfield-Jackson Atlanta Intl.
ORF
Norfolk Intl.
$125 Roundtrip, found 2 days ago
$125
Roundtrip
found 2 days ago
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