Deals on vacations and trips to Isle of Wight County

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Beautiful B&B in a cute little historic town :)

Smithfield

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Smithfield

Isle of Wight County flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Save 100% on your flight
per person
Oct 16 - Oct 19
found 22 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Families will appreciate the playground and barbecue grills. There's an outdoor pool on site, and a terrace and a picnic area are also provided.
The Capes Hotel

The Capes Hotel

3 out of 5
Northeast Virginia Beach
Save 100% on your flight
per person
Sep 26 - Sep 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
A restaurant and an indoor pool are featured at this hotel. WiFi in public areas is free. Self parking and a safe deposit box are also offered on site.
Sonesta Simply Suites Hampton

Sonesta Simply Suites Hampton

3 out of 5
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
A 24-hour gym, self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. Business travelers can take advantage of the laundry service.
The Ocean Key Virginia Beach Resort

The Ocean Key Virginia Beach Resort

3 out of 5
Northeast Virginia Beach
per person
Sep 26 - Sep 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
This aparthotel features an indoor pool, a gym, and a restaurant. Guests will appreciate free perks like free self parking and WiFi in public areas. A business center, laundry facilities, and free newspapers are also on offer.
Beach Quarters Resort

Beach Quarters Resort

2.5 out of 5
Northeast Virginia Beach
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
This hotel features an indoor pool and a gym. Enjoy the outdoor tennis court and perks like free WiFi. There's a seasonal outdoor pool on site, and a 24-hour front desk and a rooftop terrace are also provided.

Top Isle of Wight County hotels deals

Hilton Vacation Club The Historic Powhatan Williamsburg

Hilton Vacation Club The Historic Powhatan Williamsburg

3.5 out of 5
3601 Ironbound Rd, Williamsburg, VA
Free Cancellation
Reserve now, pay when you stay
$114 nightly
The price is $130 total per night
$130 total
Aug 19 - Aug 20
Total includes taxes and fees
This smoke-free resort features 2 outdoor tennis courts, an outdoor pool, and a restaurant. There's fun for all ages with a free kid's club and mini golf, and supervised childcare is an added bonus. Enjoy the indoor pool and perks like free self parking and free WiFi.
Pool
Parking included
La Quinta Inn by Wyndham Norfolk Virginia Beach

La Quinta Inn by Wyndham Norfolk Virginia Beach

3 out of 5
192 Newtown Rd, Virginia Beach, VA
Free Cancellation
Reserve now, pay when you stay
$85 nightly
The price is $99 total per night
$99 total
Sep 7 - Sep 8
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. There's a seasonal outdoor pool on site, and a 24-hour front desk and express check-in are also provided.
Pool
Breakfast included
Casa Del Mar

Casa Del Mar

2 out of 5
1010 W Ocean View Ave, Norfolk, VA
Free Cancellation
Reserve now, pay when you stay
$105 nightly
The price is $123 total per night
$123 total
Aug 18 - Aug 19
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the express check-out and free internet in public areas. There's a seasonal outdoor pool on site, and a 24-hour front desk and a garden are also provided.
Pool
Breakfast included
Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

Williamsburg Woodlands Hotel & Suites, an official Colonial Williamsburg Hotel

3 out of 5
105 Visitors Center Dr, Williamsburg, VA
$138 nightly
The price is $157 total per night
$157 total
Aug 17 - Aug 18
Total includes taxes and fees
Free water park access and an outdoor pool are featured at this smoke-free hotel. There's fun for all ages with mini golf and a children's pool, and families will appreciate the onsite laundry facilities. Enjoy the gym and free perks like continental breakfast and free self parking.
Pool
Breakfast included
Red Roof Inn Chesapeake Conference Center

Red Roof Inn Chesapeake Conference Center

2 out of 5
724 Woodlake Dr, Chesapeake, VA
Free Cancellation
Reserve now, pay when you stay
$85 nightly
The price is $99 total per night
$99 total
Aug 20 - Aug 21
Total includes taxes and fees
Free self parking is available and the hotel's front desk is staffed around-the-clock. WiFi in public areas is free. A snack bar/deli is also provided.
Pet friendly
Parking included
Wyndham Garden Williamsburg Busch Gardens Area

Wyndham Garden Williamsburg Busch Gardens Area

3 out of 5
201 Water Country Pkwy, Williamsburg, VA
Free Cancellation
Reserve now, pay when you stay
$71 nightly
The price is $82 total per night
$82 total
Aug 31 - Sep 1
Total includes taxes and fees
This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
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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.

Photos of local treasures

Browse Isle of Wight County vacation photos for more inspiration

Carrollton featuring forest scenes and a garden
Carrollton featuring farmland and a small town or village
Carrollton which includes farmland
Carrollton which includes a house and farmland
Carrollton which includes forest scenes and a garden

Frequently asked questions

How much are vacation packages to Isle of Wight County?
Travelocity has great package deals to Isle of Wight County, as well as flights and hotels, starting at just $372. With all that extra money, you could book some cool tours or possibly tack on a couple of extra days to your getaway.
Where can I get the best vacation package deals for Isle of Wight County?
With as many as 400 partner airlines and 1,000,000 properties all over the world, it's tough to beat Travelocity. Look through our impressive range and create your dream Isle of Wight County package deal. Don't you just love it when travel is that easy?
Why should I purchase my Isle of Wight County vacation package via Travelocity?
Nothing beats the feeling of knowing you've scored the best deal available — that's our Price Match Guarantee. Add to that our enormous range of destinations and 24/7 team of customer service professionals and you've got the formula for a stress-free vacation.
Will I save money on my Isle of Wight County car rental if I combine it with my hotel or flight?
You sure can. And our Isle of Wight County vacation packages are the best way to do it. In only a few clicks you can save money as well as time by combining your bookings. Pick up the keys to your rental car and feel the freedom of the open road. Need to fill your itinerary? Add some tours or experiences to your package and save on those too.
Which airport is best for Isle of Wight County?
For travelers contemplating visiting Isle of Wight County, the most used airports are Richmond Intl. Airport (RIC), Norfolk Intl. Airport (ORF) and Newport News - Williamsburg Intl. Airport (PHF).
What is there to do in Isle of Wight County?
A vibrant and thrilling destination, Isle of Wight County boasts some incredible things to see and do. Windsor Castle Park and Smithfield Farmers Market are among the favorites.