Isle of Wight County Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top destinations in Isle of Wight County

Aerial View of the Pagan River With Boats and Docks in Smithfield Virginia
FlightsFlightsHotelsHotels

Smithfield

Smithfield

Top hotels in Isle of Wight County

Vacation Village At Williamsburg

Vacation Village At Williamsburg

3 out of 5
4870 Longhill Road Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is S$190 per night from 7 Jun to 8 Jun
S$190
7 Jun - 8 Jun
includes taxes & fees
8.8/10 Excellent! (2,447 reviews)
"Friendly staff, roomy accommodations."

Reviewed on 4 Jun, 2026

Vacation Village At Williamsburg
Hilton Vacation Club The Historic Powhatan Williamsburg

Hilton Vacation Club The Historic Powhatan Williamsburg

3.5 out of 5
3601 Ironbound Rd Williamsburg VA
Fully refundableReserve now, pay when you stay
The price is S$172 per night from 22 Jun to 23 Jun
S$172
22 Jun - 23 Jun
includes taxes & fees
9/10 Wonderful! (3,475 reviews)
"We usually stay at Williansburg twice a year, but this was the first time we stayed at this place. I had to wait 45 minutes with my 4 very active grandchildren so they could get the apartment ready. Once we got in I had to get rid of the spiderwebs in the porch so kids could have a snack at the table. ..."

Reviewed on 5 Jun, 2026

Hilton Vacation Club The Historic Powhatan Williamsburg
Wingate by Wyndham Chesapeake

Wingate by Wyndham Chesapeake

3 out of 5
817 Greenbrier Circle Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is S$167 per night from 5 Jul to 6 Jul
S$167
5 Jul - 6 Jul
includes taxes & fees
7.8/10 Good! (1,063 reviews)
"It was a good stay. Would stay again."

Reviewed on 5 Jun, 2026

Wingate by Wyndham Chesapeake
See all 2,758 properties in Isle of Wight County
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 holiday package cost?
From as little as . Yes, you read that right. Our Isle of Wight County holiday 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 holiday 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 fulfil those holiday 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 travellers.
How far in advance should I book my Isle of Wight County holiday?
It can be tricky to know when is the perfect time to book your Isle of Wight County holiday. 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 holiday package is the most convenient way to organise 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 holiday 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 holiday package?
Your situation can change without warning, so yes, you can. You may be able to cancel or change your Isle of Wight County holiday 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.