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 $790, price is now $549 per person
$549
per person
Sep 27 - Oct 4
found 1 hour ago
Roundtrip flight included
Hartford (BDL) to Norfolk (ORF)
Book a stay at this 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 Kitty Hawk Beach and Jockey's Ridge State Park are located nearby.
I wish the pool was outdoors. There was no daily cleaning, you had to ask for clean towels.
Natalie at Beach Bistro was great.
Reviewed on Jul 18, 2026
John Yancey Oceanfront Inn
Save 100% on your flight
Price was $1,092, price is now $687 per person
$687
per person
Sep 27 - Oct 4
found 1 hour 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 Jockey's Ridge State Park and Kitty Hawk Beach are located nearby.
The room was not at all what I thought I was getting. I wanted an ocean view for the price I paid.. The overall room maintenance was terrible.. We left after 1 night because someone kept knocking on our door over and over and running.. Went by the office no one was there.. Definitely very disappointed
Reviewed on Jul 18, 2026
The Barclay Towers Resort Hotel
Save 100% on your flight
Price was $1,069, price is now $769 per person
$769
per person
Sep 9 - Sep 16
found 1 day ago
Roundtrip non-stop flight included
Hartford (BDL) to Norfolk (ORF)
Book a stay at this 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.
Facility was a bit worn but it was clean and the staff were friendly. Views of the ocean from the balcony were fabulous.
Reviewed on Jul 16, 2026
Delta Hotels by Marriott Virginia Beach Waterfront Suites
Save 100% on your flight
Price was $809, price is now $596 per person
$596
per person
Sep 27 - Oct 4
found 1 hour ago
Roundtrip flight included
Hartford (BDL) to Norfolk (ORF)
Book a stay at this business-friendly hotel in Virginia Beach. Enjoy free WiFi, an outdoor pool, and a beach locale. Our guests praise the restaurant and the bar in our reviews. Popular attractions Chesapeake Beach and First Landing State Park are located nearby.
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
Save 100% on your flight
Price was $837, price is now $630 per person
$630
per person
Sep 27 - Oct 4
found 1 hour ago
Roundtrip flight included
Hartford (BDL) 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 Pacific Avenue are located nearby.
Great Place just needs some touch ups it would be 10.
Reviewed on Jul 18, 2026
Holiday Inn & Suites Virginia Beach North Beach by IHG
Price was $799, price is now $610 per person
$610
per person
Sep 20 - Sep 25
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, 3 outdoor pools, and 3 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Virginia Beach Boardwalk and Neptune Statue are located nearby.
The Ocean Key Virginia Beach Resort
Save 100% on your flight
Price was $826, price is now $633 per person
$633
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Norfolk (ORF)
Stay at this 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.
First they didnt gave me the room that i pay for then there was roaches in my room then the A/c wasnt working good
Reviewed on Jul 18, 2026
The Inn at Four Eleven York
Save 100% on your flight
Price was $963, price is now $739 per person
$739
per person
Aug 26 - Aug 30
found 2 hours ago
Roundtrip flight included
Hartford (BDL) 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 Norfolk Scope and Waterside District are located nearby.
The staff was extremely helpful and the room was incredibly lovely. Would definitely recommend and stay back in this hotel anytime.
Reviewed on Jun 6, 2026
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, Sep 14 - Tue, Sep 15
ATL
Hartsfield-Jackson Atlanta Intl.
ORF
Norfolk Intl.
$82 Roundtrip, found 19 hours ago
$82
Roundtrip
found 19 hours ago
Thu, Sep 24 - Sat, Sep 26
TPA
Tampa Intl.
ORF
Norfolk Intl.
$127 Roundtrip, found 11 hours ago
$127
Roundtrip
found 11 hours ago
Tue, Aug 18 - Sun, Sep 6
MCO
Orlando Intl.
ORF
Norfolk Intl.
$138 Roundtrip, found 5 days ago
$138
Roundtrip
found 5 days ago
Wed, Sep 23 - Wed, Sep 30
BOS
Logan Intl.
ORF
Norfolk Intl.
$193 Roundtrip, found 15 hours ago
$193
Roundtrip
found 15 hours ago
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