
Isle of Wight County Vacations & Trips from $645
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Isle of Wight County Vacation
Set off on your next thrilling adventure with an Isle of Wight County vacation package, and leave relaxed knowing all the details are taken care of. And with the ability to tailor your getaway, it'll be one you won't forget. A trip to Isle of Wight County wouldn't be complete without spending a day or two in Smithfield. This city is one of the leading places to visit here. Expedia has hotels, flights and all your other travel needs to help you organize your dream Isle of Wight County vacation today.
Top destinations in Isle of Wight County

Smithfield

Carrollton
The Latest Isle of Wight County Vacation Packages
Price found within the past 48 hours. Click for updated prices.



The Sitio
Northeast Virginia Beach
Price was $1,026, price is now $938 per person
$938
per person
Dec 25 - Dec 30
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Norfolk (ORF)
9.4/10 Exceptional! (81 reviews)
Amazing hotel! Gorgeous decor and super comfortable! My husband and I enjoyed so much. He surfed all day and we relaxed in the room! Perfect!
Reviewed on Nov 6, 2026

The Inn at Four Eleven York
West Freemason
Price was $1,799, price is now $1,653 per person
$1,653
per person
Dec 27 - Jan 2
found 11 hours ago
Roundtrip flight included
Nashville (BNA) to Norfolk (ORF)
10/10 Exceptional! (116 reviews)
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
Find the Best Isle of Wight County Vacation Packages
Isle of Wight County Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Norfolk Intl. Airport (ORF) |
Top Sights | Windsor Castle Park, Carrollton Nike Park and Smithfield and Isle of Wight Visitor Center |
Isle of Wight County Hotel Deals

Hilton Vacation Club The Historic Powhatan Williamsburg
3601 Ironbound Rd Williamsburg VA
Fully refundableReserve now, pay when you stay
$92 nightly
The price is $105 total per night from Nov 15 to Nov 16
$105 total
Nov 15 - Nov 16
Total with taxes and fees
9.2/10 Wonderful! (4,006 reviews)
"Nice place to stay and convenient to everything"
Reviewed on Nov 6, 2026

Vacation Village At Williamsburg
4870 Longhill Road Williamsburg VA
Fully refundableReserve now, pay when you stay
$115 nightly
The price is $131 total per night from Nov 30 to Dec 1
$131 total
Nov 30 - Dec 1
Total with taxes and fees

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
105 Visitors Center Dr Williamsburg VA
Fully refundableReserve now, pay when you stay
$117 nightly
The price is $133 total per night from Nov 8 to Nov 9
$133 total
Nov 8 - Nov 9
Total with taxes and fees
8.8/10 Excellent! (2,066 reviews)
"The staff was really nice and welcoming, We enjoyed our weekend stay and the beautifu!"
Reviewed on Nov 6, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Stay near popular Isle of Wight County attractions
What to do in Isle of Wight County

Williamsburg: Colonial Williamsburg Admission
$39
per adult

Speak Easy Murder Mystery Dinner Show at Kings Creek Williamsburg
$55
per adult
100% of travellers recommend

Virginia: speakeasy-themed murder mystery dinner at King ́s C
$60
per adult
Explore a world of travel with Expedia
Other vacations you might like
- Top cities in Isle of Wight County
- Vacations and getaways similar to Isle of Wight County
- Best vacation destinations by month
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.






















