Isle of Wight County Vacation Packages

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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.
Sea Ranch Resort

Sea Ranch Resort

3 out of 5
Price was CA $2,038, price is now CA $1,471 per person
CA $1,471
per person
Jul 18 - Jul 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Norfolk (ORF)
8.6/10 Excellent! (1,007 reviews)
Nice place, right on the beach

Reviewed on May 9, 2026

Pamlico Station Edgecamp

Pamlico Station Edgecamp

2 out of 5
South Rodanthe
Price was CA $2,788, price is now CA $1,898 per person
CA $1,898
per person
Jul 18 - Jul 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Norfolk (ORF)
9.4/10 Exceptional! (33 reviews)
Very unique spot. Javi the concierge was super helpful. Staff was also on site periodically or could be called to come if needed. Unit was beautiful and clean with lots of amenities. We especially liked the hot tub and sauna on the deck

Reviewed on May 18, 2026

Sea Scape Beach and Golf Villas

Sea Scape Beach and Golf Villas

3.5 out of 5
Sea Scape
Price was CA $2,240, price is now CA $1,638 per person
CA $1,638
per person
Jul 18 - Jul 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Norfolk (ORF)
9.2/10 Wonderful! (153 reviews)
The property was as we expected. A few very minor problems (a light in the livingroom did not work-there werelots of

Reviewed on May 14, 2026

Sanderling Resort Residences

Sanderling Resort Residences

4 out of 5
Price was CA $5,983, price is now CA $4,602 per person
CA $4,602
per person
Jul 18 - Jul 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Norfolk (ORF)
No reviews
John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Price was CA $2,247, price is now CA $1,777 per person
CA $1,777
per person
Jul 18 - Jul 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Norfolk (ORF)
9.2/10 Wonderful! (1,899 reviews)
New, clean, very friendly staff. Great breakfast and right on the ocean. Beautiful!

Reviewed on May 12, 2026

Isle of Wight County Hotel Deals

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 CA $109 per night from May 31 to Jun 1
CA $109
CA $140 total
May 31 - Jun 1
includes taxes & fees
8.8/10 Excellent! (2,407 reviews)
Beautiful and well maintained property close to restaurants and shopping.

Reviewed on May 18, 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 CA $127 per night from Jun 1 to Jun 2
CA $127
CA $184 total
Jun 1 - Jun 2
includes taxes & fees
9/10 Wonderful! (3,478 reviews)
Had a few minor inconveniences, such as the body wash and conditioners being empty and it taking two days and two requests to get more. Additionally, the activity room and building with the pool was under construction, and the chlorine level in the pool was such that our skin (myself and one of my ...

Reviewed on May 18, 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 CA $136 per night from May 25 to May 26
CA $136
CA $160 total
May 25 - May 26
includes taxes & fees
8/10 Very Good! (1,042 reviews)
Breakfast was nice and pool was closed with only 1 elevator working. The room smelled of cigarette badly and was informed by the front desk that the reason was the entire hotel is on one ventilation system which causes the smoke smell to spread through the rooms but not the halls. The bathroom desperately ...

Reviewed on May 17, 2026

Wingate by Wyndham Chesapeake
See all 2,866 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.
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Frequently asked questions

How much does an Isle of Wight County vacation package cost?
From as little as CA $1,471. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.