Search Deals onChesapeake Vacation Packages
Chesapeake Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Stonewood Inn & Suites Carrollton - Smithfield
Price was $607, price is now $533 per person
$533
per person
Dec 10 - Dec 15
found 2 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Stay at this hotel in Smithfield. Enjoy free WiFi, free parking, and a garden. Popular attractions Serendipity Meadworks and Carrollton Nike Park are located nearby.
The room was clean and comfortable- the pillows were hard, so if you like a soft pillow, be sure to bring your own! Great location, nice staff. I slept well. My room door stuck, but a little hip bump opened it.
Reviewed on Nov 10, 2026
The Inn at Four Eleven York
Price was $1,299, price is now $1,020 per person
$1,020
per person
Jan 10 - Jan 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Stay at this 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 Norfolk Premium Outlets are located nearby.
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
Price was $887, price is now $713 per person
$713
per person
Jan 10 - Jan 16
found 1 day 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 First Landing State Park are located nearby.
Holiday Inn & Suites Virginia Beach North Beach by IHG
Price was $734, price is now $598 per person
$598
per person
Jan 10 - Jan 16
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, 3 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Virginia Beach Boardwalk and First Landing State Park are located nearby.
Crowne Plaza Virginia Beach Town Center by IHG
Price was $708, price is now $599 per person
$599
per person
Jan 10 - Jan 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Book a stay at this business-friendly hotel in Virginia Beach. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions Veterans United Home Loans Amphitheater at Virginia Beach and Norfolk Premium Outlets are located nearby.
Residence Inn by Marriott Norfolk Airport
Price was $793, price is now $688 per person
$688
per person
Jan 10 - Jan 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Book a stay at this business-friendly hotel in Norfolk. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Norfolk Premium Outlets and Waterside District are located nearby.
Staybridge Suites Norfolk Airport by IHG
Price was $859, price is now $757 per person
$757
per person
Jan 10 - Jan 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Stay at this hotel in Norfolk. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Norfolk Premium Outlets and Waterside District are located nearby.
Nice!
Reviewed on Nov 8, 2026
Ocean View Inn
Price was $3,817, price is now $3,371 per person
$3,371
per person
Jan 10 - Jan 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Book a stay at this beach motel in Norfolk. Enjoy free WiFi, a private beach, and a 24-hour front desk. Popular attractions Norfolk Premium Outlets and Norfolk Beaches 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.
Fri, Dec 11 - Mon, Dec 14
ATL
Hartsfield-Jackson Atlanta Intl.
ORF
Norfolk Intl.
$118 Roundtrip, found 2 hours ago
$118
Roundtrip
found 2 hours ago
Thu, Dec 10 - Sat, Dec 12
MCO
Orlando Intl.
ORF
Norfolk Intl.
$138 Roundtrip, found 4 hours ago
$138
Roundtrip
found 4 hours ago
Wed, Dec 9 - Mon, Dec 14
TPA
Tampa Intl.
ORF
Norfolk Intl.
$143 Roundtrip, found 7 hours ago
$143
Roundtrip
found 7 hours ago
Wed, Dec 2 - Fri, Dec 11
DFW
Dallas-Fort Worth Intl.
ORF
Norfolk Intl.
$204 Roundtrip, found 1 hour ago
$204
Roundtrip
found 1 hour ago
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