Search Deals onChesapeake Vacation Packages
Chesapeake Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Sea Ranch Resort
Save 100% on your flight
Price was $667, price is now $439 per person
$439
per person
Oct 14 - Oct 21
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.

John Yancey Oceanfront Inn
Save 100% on your flight
Price was $1,009, price is now $578 per person
$578
per person
Oct 14 - Oct 21
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.

Boardwalk Resort and Villas
Save 100% on your flight
Price was $1,023, price is now $595 per person
$595
per person
Oct 14 - Oct 21
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.

Beach Quarters Resort
Save 100% on your flight
Price was $722, price is now $441 per person
$441
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip 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.

Sanderling Resort Residences
Save 100% on your flight
Price was $5,955, price is now $4,000 per person
$4,000
per person
Oct 14 - Oct 21
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.

Sea Scape Beach and Golf Villas
Save 100% on your flight
Price was $851, price is now $612 per person
$612
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Stay at this 3.5-star golf condo in Kitty Hawk. Enjoy free parking, 2 outdoor pools, and a fitness center. Popular attractions Sea Scape Golf Links and Monument to a Century of Flight are located nearby.

Hilton Norfolk The Main
Save 100% on your flight
Price was $1,920, price is now $1,401 per person
$1,401
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Stay at this 4-star business-friendly hotel in Norfolk. Enjoy 3 restaurants, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Waterside District and Greenbrier Mall are located nearby.

Outer Banks Beach Club
Save 100% on your flight
Price was $720, price is now $527 per person
$527
per person
Oct 14 - Oct 21
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 WiFi, free parking, and 2 outdoor pools. Popular attractions Destination Fun and Stop-N-Shop Beach Shop 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.

Sat, Sep 27 - Mon, Sep 29
TPA
Tampa Intl.
ORF
Norfolk Intl.
$107 Roundtrip, found 1 day ago
$107
Roundtrip
found 1 day ago

Fri, Sep 26 - Mon, Sep 29
JAX
Jacksonville Intl.
ORF
Norfolk Intl.
$107 Roundtrip, found 1 day ago
$107
Roundtrip
found 1 day ago

Thu, Sep 18 - Thu, Sep 25
MCO
Orlando Intl.
ORF
Norfolk Intl.
$110 Roundtrip, found 2 days ago
$110
Roundtrip
found 2 days ago

Tue, Oct 21 - Sat, Oct 25
ATL
Hartsfield-Jackson Atlanta Intl.
ORF
Norfolk Intl.
$144 Roundtrip, found 2 days ago
$144
Roundtrip
found 2 days ago
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