Search Deals onChesapeake Vacation Packages
Chesapeake Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Boardwalk Resort and Villas
Save 100% on your flight
per person
Oct 2 - Oct 7
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 Pacific Avenue are located nearby.
Beach Quarters Resort
Save 100% on your flight
per person
Oct 2 - Oct 7
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.
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
Save 100% on your flight
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip 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 Pacific Avenue are located nearby.
Pamlico Station Edgecamp
Save 100% on your flight
per person
Aug 29 - Aug 31
found 12 hours ago
Roundtrip flight included
Hartford (BDL) 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.
The Ocean Key Virginia Beach Resort
Save 100% on your flight
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
Stay at this 3-star 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 Sanderling
Save 100% on your flight
per person
Oct 19 - Oct 24
found 15 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.
Hilton Norfolk The Main
Save 100% on your flight
per person
Oct 8 - Oct 12
found 7 hours ago
Roundtrip non-stop flight included
Hartford (BDL) 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.
John Yancey Oceanfront Inn
Save 100% on your flight
per person
Aug 29 - Aug 31
found 12 hours ago
Roundtrip flight included
Hartford (BDL) 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.
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.
Mon, Oct 20 - Sat, Oct 25
ATL
Hartsfield-Jackson Atlanta Intl.
ORF
Norfolk Intl.
$70 Roundtrip, found 2 days ago
$70
Roundtrip
found 2 days ago
Thu, Aug 14 - Thu, Aug 21
MCO
Orlando Intl.
ORF
Norfolk Intl.
$80 Roundtrip, found 1 day ago
$80
Roundtrip
found 1 day ago
Thu, Oct 16 - Sun, Oct 19
DFW
Dallas-Fort Worth Intl.
ORF
Norfolk Intl.
$98 Roundtrip, found 2 days ago
$98
Roundtrip
found 2 days ago
Wed, Sep 17 - Sat, Sep 20
JAX
Jacksonville Intl.
ORF
Norfolk Intl.
$102 Roundtrip, found 2 days ago
$102
Roundtrip
found 2 days ago
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