Isle of Wight Vacations from $428

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Your Isle of Wight Vacation

Excellent adventures await when you lock in a Isle of Wight vacation package. Whether you're a foodie, history enthusiast or just a traveler who loves to discover new places, there's something for everyone in this vibrant city. If sightseeing is on your to-do list during your trip to Isle of Wight, stop by well-known attractions such as Boykins Tavern. A few clicks is all it takes to put together a tailored Isle of Wight vacation on Expedia.

The Latest Isle of Wight Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Jan 13 - Jan 16

    John Yancey Oceanfront Inn + Flight

    Kill Devil Hills
    3 nights
    2.0 star property
    9.2/10 - Wonderful (1,961 reviews)
    "Very clean rooms and friendly staff."
    Reviewed November 3, 2026
    Roundtrip • San Antonio (SAT) - Norfolk (ORF)
    SAT - ORF • 1 stop ORF - SAT • 1 stop
    $543
    $428
    per traveler
    found 1 day ago
    John Yancey Oceanfront Inn
  • Dec 5 - Dec 11

    Holiday Inn & Suites Virginia Beach North Beach by IHG + Flight

    Northeast Virginia Beach
    6 nights
    3.0 star property
    8.0/10 - Very good (1,587 reviews)
    "Clean room but they were upgrading the 3rd floor & it was noisy early in the morning."
    Reviewed November 1, 2026
    Roundtrip • Detroit (DTW) - Norfolk (ORF)
    DTW - ORF • Nonstop ORF - DTW • Nonstop
    $900
    $704
    per traveler
    found 4 hours ago
    Holiday Inn & Suites Virginia Beach North Beach by IHG
  • Jan 14 - Jan 18

    Boardwalk Resort and Villas + Flight

    Northeast Virginia Beach
    4 nights
    3.0 star property
    8.8/10 - Excellent (1,006 reviews)
    Roundtrip • New York (NYC) - Norfolk (ORF)
    JFK - ORF • Nonstop ORF - JFK • Nonstop
    $549
    $441
    per traveler
    found 1 day ago
    Boardwalk Resort and Villas
  • Jan 14 - Jan 18

    Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia + Flight

    Northeast Virginia Beach
    4 nights
    4.0 star property
    8.2/10 - Very good (1,451 reviews)
    Roundtrip • New York (NYC) - Norfolk (ORF)
    JFK - ORF • Nonstop ORF - LGA • Nonstop
    $662
    $542
    per traveler
    found 1 day ago
    Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
  • Dec 10 - Dec 13

    The Sitio + Flight

    Northeast Virginia Beach
    3 nights
    4.0 star property
    9.6/10 - Exceptional (87 reviews)
    Roundtrip • New York (JFK) - Norfolk (ORF)
    JFK - ORF • Nonstop ORF - JFK • Nonstop
    $909
    $749
    per traveler
    found 18 hours ago
    The Sitio

Discover the most popular places to visit in Isle of Wight

Isle of Wight Hotel Deals

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.

Find out more about Isle of Wight

Things to do near Isle of Wight

Isle of Wight, Virginia, offers a delightful blend of outdoor adventures and scenic beach vacations. Visitors can enjoy activities like golf, sightseeing tours, and exploring free attractions. With its picturesque landscapes, the area is perfect for outdoor enthusiasts looking for free adventures, making it an ideal destination for a relaxing getaway filled with nature and leisure.

Shopping

The Smithfield Farmers Market, only 6 miles away, offers a vibrant atmosphere with local produce and artisan goods. If you're up for a drive, Chesapeake Square Mall, 17 miles away, features a variety of stores and entertainment options, while the Planters Peanut Center, 14 miles away, is perfect for unique gifts.

Recreation

Carrollton Nike Park offers a peaceful environment for leisurely walks and picnics, located 9 miles from Isle of Wight. Huntington Park, situated 16 miles away, features walking trails and serene lake views perfect for relaxation. Boo Williams Sportplex, 21 miles away, provides facilities for sports and fitness activities.

Adventure

Experience thrills at Bounce House, an exciting arcadeAdventureZone located 18 miles from Isle of Wight, perfect for family fun. For tennis enthusiasts, the Huntington Park Tennis Center, located 16 miles away, offers a vibrant atmosphere. Don't miss the Buckroe Beach Carousel, an amusement ride 22 miles away, for nostalgic enjoyment.

Nightlife

In Isle of Wight, Virginia, enjoy a relaxed nightlife with local bars and eateries. Check out waterfront spots offering live music and craft cocktails. The atmosphere is friendly, perfect for unwinding after a day of exploration, with options to socialize or enjoy a quiet evening by the water.

Find the best attractions near Isle of Wight

Isle of Wight, Virginia, is perfect for outdoor enthusiasts and beach lovers, offering scenic views and a rich cultural experience. Visitors can explore historic sites, entertainment arenas, and visitor centers that cater to families and adventure seekers alike. Whether you're looking for a relaxing holiday or exciting activities, there's plenty to discover in and around Isle of Wight, making it a fantastic destination for your next vacation.

  • Windsor Castle Park: Situated 6 miles from Isle of Wight, Windsor Castle Park is an urban oasis perfect for families. Enjoy scenic walking trails, picnic areas, and beautifully landscaped gardens, all while soaking in the vibrant city atmosphere.
  • Christopher Newport University: Located 16 miles away, this modern college campus boasts stunning architecture and a lively ambiance. Explore its art galleries, attend events, and appreciate the unique blend of academic life and city vibes.
  • Smithfield and Isle of Wight Visitor Center: Just 6 miles from Isle of Wight, this visitor center offers adventurous outdoor activities and family-friendly attractions. Discover local history, enjoy guided tours, and immerse yourself in the region's natural beauty.

Best time to go to Isle of Wight

The best time to visit Isle of Wight is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain.

Tips to save on your trip to Isle of Wight

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Isle of Wight.
  • Consider traveling to Isle of Wight during the low season (January to March) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Frequently Asked Questions

What's included in an Isle of Wight vacation package?

An Isle of Wight vacation package lets you combine round-trip flights, hotel stays, and rental cars for a convenient trip. Isle of Wight vacation packages often feature stays with easy access to the coastline, reflecting the destination's reputation for beautiful beaches. Many hotels also offer convenient airport shuttle services from nearby hubs like Norfolk International Airport (ORF) or Richmond International Airport (RIC), and some include daily breakfast to start your day.


Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.

How can I save money on a Isle of Wight vacation package?

When you bundle, you can save up to 30%*. To save money on a Isle of Wight package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

Is Isle of Wight better suited for a beach vacation or a cultural trip?

Isle of Wight is primarily a beach destination, making it ideal for travelers seeking coastal relaxation and outdoor activities. Its natural setting outside a city provides a tranquil backdrop for a relaxing Isle of Wight vacation.


While beaches are a main draw, the area also offers historical insights. You can explore sites like Boykin's Tavern, located about a 5-minute walk from central Isle of Wight, which provides a glimpse into local heritage. Therefore, an Isle of Wight vacation package can combine beach time with historical exploration.

What are the top things to do in Isle of Wight?

Isle of Wight offers a variety of attractions for your Isle of Wight vacation, from historical sites to family entertainment:


Browse and book things to do in Isle of Wight on Expedia.

Do you need to rent a car in Isle of Wight, or is public transport enough?

For an Isle of Wight vacation, renting a car is generally recommended to fully explore the area. As an outdoor and nature destination outside a city, the island's attractions and natural sights can be spread out, making a car ideal for flexibility.


Having a car allows you to easily reach various points of interest and beaches, enhancing your Isle of Wight vacation packages with flights. This is especially true if you plan to explore beyond your immediate accommodation or enjoy day trips.

Can I change or cancel my Isle of Wight vacation package if my plans change?

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Do One Key members get extra savings when booking Isle of Wight vacation packages?

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

Does Expedia offer Book Now, Pay Later Isle of Wight vacation packages?

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Isle of Wight vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

How do I find last-minute vacation packages to Isle of Wight?

To find last-minute vacation packages to Isle of Wight, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

How does free cancellation work on Isle of Wight vacation packages?

Free cancellation on a Isle of Wight vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

Is it cheaper to book a Isle of Wight vacation as a package or separately?

Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Isle of Wight getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Why should I book my Isle of Wight vacation package with Expedia?

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.