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

Hilton Vacation Club Ocean Beach Club Virginia Beach
Price was $539, price is now $495 per person
$495
per person
Dec 10 - Dec 15
found 7 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Book a stay at this beach hotel in Virginia Beach. Enjoy free WiFi, 2 indoor pools, 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.
Very clean room. Loved the kitchenette. Had everything I needed and was very clean and organized. People were amazing. Front desk folks were super helpful and helped me find restaurants nearby. Thank you!!
Reviewed on Nov 6, 2026

The Sitio
Price was $997, price is now $888 per person
$888
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Stay at this hotel in Virginia Beach. Enjoy free WiFi, parking (surcharge), and in-room massages. Popular attractions Virginia Beach Boardwalk and First Landing State Park are located nearby.

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
Price was $816, price is now $733 per person
$733
per person
Dec 27 - Dec 31
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.

Blufin Bungalows & Marina
Price was $638, price is now $574 per person
$574
per person
Dec 12 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Stay at this vacation home in Chincoteague. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Chincoteague Channel and Assateague Point are located nearby.
We had a wonderful stay! The bungalow was nice, clean, and peaceful. It was the perfect place to relax and unwind. Would definitely stay again!
Reviewed on Nov 1, 2026

Holiday Inn & Suites Virginia Beach North Beach by IHG
Price was $614, price is now $555 per person
$555
per person
Dec 10 - Dec 15
found 7 hours 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.
Clean room but they were upgrading the 3rd floor & it was noisy early in the morning.
Reviewed on Nov 1, 2026

Hilton Vacation Club Oceanaire Virginia Beach
Price was $625, price is now $564 per person
$564
per person
Dec 10 - Dec 15
found 7 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Book a stay at this beach hotel in Virginia Beach. Enjoy free WiFi, a beach locale, and a fitness center. 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.
Staff very knowledgeable, friendly and helpful.
Reviewed on Nov 5, 2026

Hyatt House Virginia Beach / Oceanfront
Price was $923, price is now $837 per person
$837
per person
Dec 10 - Dec 15
found 3 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
Book a stay at this beach hotel in Virginia Beach. Enjoy free breakfast, free WiFi, and a beach locale. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Virginia Beach Boardwalk and First Landing State Park are located nearby.
The property is Ocean Front. And the views are stunning. The staff was friendly, extremely helpful with suggestions for area activities and restaurants. Breakfast was until 10:30 so sleeping in was an option and they continued to bring hot food out until that time.
Reviewed on Nov 4, 2026

The Inn at Four Eleven York
Price was $984, price is now $902 per person
$902
per person
Jan 7 - Jan 11
found 8 hours 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.
We stayed for our honeymoon before embarking on our cruise to Bermuda out of Norfolk. The port was very close to the Inn.
The Inn is beautiful and so romantic. The area around the Inn had several options for dining. The walkable area was so romantic with its old architecture and cobblestone streets.
I would love to come and stay longer and experience their restaurants and the city of Norfolk. I would highly recommend the Inn to anyone wanting a place that is not a big box type hotel. If you want charm and romance this place is for you!!!!
Reviewed on Oct 20, 2026
Windsor Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Windsor 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, Dec 5 - Wed, Dec 9
ATL
Hartsfield-Jackson Atlanta Intl.
ORF
Norfolk Intl.
$118 Roundtrip, just found
$118
Roundtrip
just found

Thu, Jan 7 - Tue, Jan 12
MCO
Orlando Intl.
ORF
Norfolk Intl.
$135 Roundtrip, found 18 hours ago
$135
Roundtrip
found 18 hours ago

Wed, Dec 9 - Mon, Dec 14
TPA
Tampa Intl.
ORF
Norfolk Intl.
$136 Roundtrip, found 9 hours ago
$136
Roundtrip
found 9 hours ago

Sat, Dec 5 - Sat, Dec 12
DFW
Dallas-Fort Worth Intl.
ORF
Norfolk Intl.
$206 Roundtrip, found 10 hours ago
$206
Roundtrip
found 10 hours ago
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