Isle of Wight Vacations 2026 from CA $995

Search vacation packages deals in Isle of Wight's top destinations

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Isle of Wight flight + hotel packages

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Alton House Hotel

CA $995

per person

Feb 16 - Feb 21

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Southampton (SOU)

Book a stay at this business-friendly hotel in Alton. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions Curtis Museum and Allen Gallery are located nearby.

Winchester Wessex Hotel by Sunday

CA $1,245

per person

Jan 18 - Jan 24

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Southampton (SOU)

Book a stay at this business-friendly hotel in Winchester. Enjoy free WiFi, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Winchester Christmas Market and Winchester Guildhall are located nearby.

Hampshire Court Hotel & Spa

CA $1,218

per person

Feb 2 - Feb 6

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Southampton (SOU)

Book a stay at this spa hotel in Basingstoke. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Mill Field Nature Reserves and Basing House are located nearby.

Warbrook House Heritage Hotel

CA $1,092

per person

Jan 19 - Jan 25

found 12 hours ago

Roundtrip non-stop flight included

Vancouver (YVR) to Southampton (SOU)

Book a stay at this business-friendly hotel in Hook. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions California Country Park and Sean Devereux Park are located nearby.

Top Isle of Wight hotels deals

Royal Esplanade Hotel

16 The Esplanade Ryde England

Free cancellation

Reserve now, pay when you stay

Get rates

Book a stay at this beach hotel in Ryde. Enjoy free breakfast, 2 bars/lounges, and parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Gunwharf Quays and Portsmouth Historic Dockyard are located nearby.

Breakfast included

Free WiFi

Ryde Castle Hotel by Greene King Inns

The Esplanade Ryde England

Free cancellation

Reserve now, pay when you stay

CA $97

CA $116 total

Dec 26 - Dec 27

includes taxes & fees

Book a stay at this luxury inn in Ryde. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Gunwharf Quays and Portsmouth Historic Dockyard are located nearby.

Parking included

Free WiFi

Whitecliff Bay Holiday Park

Hillway Road Bembridge England

Get rates

Book a stay at this family-friendly holiday park in Bembridge. Enjoy free parking, an outdoor pool, and a beach locale. Popular attractions Whitecliff Bay Beach and Bembridge Beach are located nearby.

Pool

Pet-friendly

The Brunswick

Queen's Road Shanklin England

CA $107

CA $129 total

Dec 19 - Dec 20

includes taxes & fees

Stay at this hotel in Shanklin. Enjoy free breakfast, an outdoor pool, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Shanklin Beach and Shanklin Theatre are located nearby.

Pool

Breakfast included

Luccombe Manor Country House Hotel

11 Popham Road Shanklin England

CA $154

CA $185 total

Jan 12 - Jan 13, 2026

includes taxes & fees

Book a stay at this family-friendly hotel in Shanklin. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Rylstone Gardens and Shanklin Chine are located nearby.

Pool

Hot tub

One Holyrood Hotel

1-4 Holyrood Street Newport England

Free cancellation

Reserve now, pay when you stay

CA $207

CA $249 total

Dec 17 - Dec 18

includes taxes & fees

Stay at this hotel in Newport. Enjoy breakfast (surcharge), parking (surcharge), and daily housekeeping. Popular attractions Seaclose Park and Carisbrooke Castle are located nearby.

Pet-friendly

Free WiFi

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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.

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Frequently asked questions

How much are vacation packages to Isle of Wight?

With vacation packages being sold from just CA $995, there's no need to max out the credit card for your trip to Isle of Wight. Travelocity can help. Combine experiences, flights and hotels into a convenient package and walk away with fantastic discounts. The more you book, the greater the savings.

Where can I get the best vacation package deals for Isle of Wight?

There are incredible Isle of Wight package deals to be gained with Travelocity. Did you know we partner with 400 airlines and 1,000,000 properties across the globe? Remember this the next time you're ready to cross another place off the old bucket list.

Why should I book my Isle of Wight vacation bundle with Travelocity?

Because life is an amazing journey, and we've got everything you need to help you on your way. With our top-quality service and Price Match Guarantee, you can organize your trip with confidence. And you can rest easy while you're away knowing we've got you covered with our 24/7 customer support.

Can I save on my Isle of Wight car rental if I bundle it with a hotel or flight?

You sure can with our Isle of Wight vacation packages. With one of these, there are lots of ways to make your vacation budget go further. Bundle any two or more car, flight, hotel and tour bookings and see the savings pile up. With your own set of wheels, all the popular sights in and around Isle of Wight are a memorable road trip away.

Which airport is best for Isle of Wight?

Gatwick Airport (LGW) is a popular choice for Isle of Wight visitors. But depending on what you plan to do, Southampton Airport (SOU) or Bournemouth Intl. Airport (BOH) could be more convenient.