Isle of Wight County Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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 Isle of Wight County Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
Northeast Virginia Beach
CA $1,189
per person
Oct 9 - Oct 13
found 12 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Norfolk (ORF)
8.2/10 Very good! (1,380 reviews)
I go every year for my mini vacation! I love it here!
Reviewed on Sep 2, 2026
Isle of Wight County Hotel Deals
Vacation Village At Williamsburg
4870 Longhill Road Williamsburg VA
Fully refundableReserve now, pay when you stay
CA $118
CA $150 total
Sep 21 - Sep 22
includes taxes & fees
Hilton Vacation Club The Historic Powhatan Williamsburg
3601 Ironbound Rd Williamsburg VA
Fully refundableReserve now, pay when you stay
CA $93
CA $146 total
Sep 9 - Sep 10
includes taxes & fees
9.2/10 Wonderful! (3,791 reviews)
"It was a wonderful trip!!!!!"
Reviewed on Sep 2, 2026
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel
105 Visitors Center Dr Williamsburg VA
Fully refundableReserve now, pay when you stay
CA $104
CA $151 total
Sep 8 - Sep 9
includes taxes & fees
8.8/10 Excellent! (1,944 reviews)
"It is worth staying here if you are going to Colonial Williamsburg. The hotel parking lot is essentially the visitors' center parking lot, and the hotel gives you a pass to park for free. They also give you a coupon for a discount on tickets to Colonial Williamsburg. I loved the huge (Olympic-sized?) ..."
Reviewed on Sep 3, 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.
Frequently asked questions
How much does an Isle of Wight County vacation package cost?
From as little as CA $1,148. Yes, you read that right. Our Isle of Wight County vacation packages are a great way to make your budget last longer. Bundle your preferred hotels, flights and rental car and explore this destination your way.
How do I get a cheap travel package to Isle of Wight County?
Simply by bundling. Hotels, flights and rental cars — combine whatever you need into an Isle of Wight County vacation package to save loads of cash. Score even more deals when you add extras such as experiences or tours to your booking. But that's not the only good part. You have the freedom to customize your trip your own way. We offer over 550 airlines and 1,000,000 hotels worldwide, so that everyone has an opportunity to travel and fulfill those vacation dreams.
What are the top hotels in Isle of Wight County?
Hampton Inn Suites Smithfield and Econo Lodge Carrollton Smithfield know how to make their guests feel at home in Smithfield. If your travel plans also include Carrollton, have a look at Smithfield Station and Smithfield Inn. Both are very popular with travelers.
How far in advance should I book my Isle of Wight County vacation?
It can be tricky to know when is the perfect time to book your Isle of Wight County vacation. But typically the earlier you book, the better the prices. Sometimes, you can reserve your flights and hotels up to a year prior to departure. If you're hoping for a last-minute getaway, no need to fret! There are fantastic deals featured on Expedia every day.
What should I know before booking an Isle of Wight County travel package?
Bundling your bookings into an Isle of Wight County vacation package is the most convenient way to organize your trip. Not only that, you'll save big when you combine your flights, hotels and car rentals. Once you've booked, why not add on a day tour or an activity?
Can I choose my airline with an Isle of Wight County Expedia vacation package?
Yes, definitely. Expedia has over 550 airline partners to choose from across the world. With all that choice at your fingertips, finding the ideal carrier to fly you to Isle of Wight County will be easy.
If I'm not able to travel, can I cancel my Isle of Wight County vacation package?
Your situation can change without warning, so yes, you can. You may be able to cancel or change your Isle of Wight County vacation package at no cost if you've booked in the last 24 hours. For bookings made more than 24 hours ago, you can still cancel and rebook, but your airline, hotel or car rental company may charge additional fees. Want more information? Have a look at our Customer Service Portal. We're here to help make sure your getaway goes off without a hitch.
Stay near popular Isle of Wight County attractions
Windsor Castle Park
9.0/10 (12 reviews)
Explore the great outdoors at Windsor Castle Park, a lovely green space in Smithfield. Experience the area's live music or attend a sporting event.
Photo by Kaylee Spinhirn
Smithfield Historic District
You can find out about the history of Smithfield with a trip to Smithfield Historic District. Discover the live music and churches in this family-friendly area.
Smithfield and Isle of Wight Visitor Center
8.0/10 (12 reviews)
After visiting Smithfield and Isle of Wight Visitor Center, make a plan to see the other sights and activities in Smithfield. Experience the area's live music or attend a sporting event.
Fort Boykin
7.4/10 (3 reviews)
You can learn about the history of Smithfield with a visit to Fort Boykin. You can attend a sporting event while in the area.
Carrollton Nike Park
10.0/10 (1 review)
You can learn about the history of Carrollton with a trip to Carrollton Nike Park. You can attend a sporting event while in the area.
Isle of Wight County Museum
8.0/10 (6 reviews)
You can study the exhibits at Isle of Wight County Museum, a museum with a storied past, during your travels to Smithfield. Experience the area's live music or attend a sporting event.
Smithfield Farmers Market
9.0/10 (12 reviews)
You can do some window-shopping at Smithfield Farmers Market during your trip to Smithfield. Experience the area's live music or attend a sporting event.
Boykin's Tavern
8.0/10 (1 review)
You can study the exhibits at Boykin's Tavern, a museum with a storied past, during your trip to Isle of Wight. Discover the area's live music and churches.
What to do in Isle of Wight County
Colonial Williamsburg: Colonial History Guided Walking Tour
CA $35
per adult
100% of travellers recommend
Williamsburg Ghosts, Witches and Pirates Tour
CA $35
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
