Isle of Wight Vacations & Trips from $1,661

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Top destinations in Isle of Wight

A pier extending into the water with a sunset in the background.

Bembridge

Bembridge
A wide sandy beach with gentle waves, a distant ship, and a line of trees along the shore.

Ryde

Ryde
A long pier extending into calm waters with a cloudy sky.

Sandown

Sandown
A coastal town with a sandy beach, green-roofed beach huts, and a calm sea.

Cowes

Cowes
A coastal path with cliffs, a beach, and a distant town.

Ventnor

Ventnor
A historic stone building complex with a prominent tower, surrounded by lush greenery and a clear sky.

Newport

Newport
A coastal town with a sandy beach, houses, and a cliff overlooking the sea.

Freshwater

Freshwater

The Latest Isle of Wight Vacation Packages

Price found within the past 48 hours. Click for updated prices.
South Winchester Lodges

South Winchester Lodges

$1,661
per person
Nov 6 - Nov 11
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Southampton (SOU)
9.6/10 Exceptional! (42 reviews)
Lovely lodge, clean and appreciated the birthday balloons. Good communication and excellent location in winchester with new forest short driving distance. We went to go for breakfast on last day at the golf club but found them unfriendly with a cold atmosphere. The lodge however was fab!

Reviewed on Aug 29, 2026

Smart Apartments - Seymour

Smart Apartments - Seymour

Bassett
$1,889
per person
Oct 24 - Oct 31
found 7 hours ago
Roundtrip flight included
Singapore (SIN) to Southampton (SOU)
No reviews
Serene Riverside 6BR Luxury Retreat in Curdridge

Serene Riverside 6BR Luxury Retreat in Curdridge

$3,372
per person
Nov 6 - Nov 11
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Southampton (SOU)
No reviews
Newly Refurbished 3 Bed Apartment Free Parking

Newly Refurbished 3 Bed Apartment Free Parking

Bassett Green
$1,720
per person
Nov 6 - Nov 11
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Southampton (SOU)
No reviews
Best Western Chilworth Manor Hotel

Best Western Chilworth Manor Hotel

$1,677
per person
Oct 26 - Oct 31
found 23 hours ago
Roundtrip flight included
Zhengzhou (CGO) to Southampton (SOU)
8/10 Very Good! (1,000 reviews)

Best Places to Vacation in Isle of Wight

1. Find your perfect Ryde vacation

Ryde, England is a perfect destination for outdoor enthusiasts seeking a relaxing yet adventurous vacation. With its friendly locals, beautiful marina, and convenient ferry access to nearby islands, Ryde offers a unique experience. The stunning sea views and opportunities for water activities make it an ideal place for adventure seekers. For those on a budget, there are plenty of affordable options including bars and restaurants. History buffs will enjoy exploring Ryde Castle, adding a touch of culture to their vacation. Whether you're looking for a peaceful getaway or an action-packed adventure, Ryde has something for everyone.

  • The peak season is from June to August
  • The off-peak season is from October to December
  • Travelers tend to stay 3 days in Ryde

2. Create memories in Sandown with a vacation package

Sandown, located in England's United Kingdom, offers a charming atmosphere perfect for outdoor vacations. With its friendly locals, beautiful beaches, and nearby islands, it's an ideal destination for relaxation and exploration. Golf enthusiasts can enjoy the scenic golf courses, while those seeking a bit of pampering can indulge in spa treatments. Swimming in the crystal-clear sea is a must, and art lovers will appreciate the local galleries. Coffee lovers can savor a cup of their favorite brew while enjoying the stunning coastal views. Excursions to nearby attractions and activities like aquariums and zoos are popular among travelers.

  • The peak season is from June to August
  • The off-peak season is from October to December
  • Travelers tend to stay 5 days in Sandown

3. Book your ideal Ventnor with a vacation package

Ventnor, located in England's United Kingdom, offers a delightful outdoor vacation experience. With its stunning gardens, natural parks, and nearby islands, the region is a paradise for nature lovers. The town also boasts a rich cultural scene, allowing visitors to immerse themselves in local traditions and heritage. The beautiful beach and golf courses provide opportunities for relaxation and recreation, while the sea offers thrilling adventures. Ventnor is a charming small town filled with historical monuments, making it a perfect destination for those seeking a blend of natural beauty and cultural exploration.

  • Travelers tend to stay 3 days in Ventnor

4. Discover Newport with our vacation deals

Newport, England offers a unique outdoor vacation experience with its stunning geography. Situated on an island, visitors can explore magnificent castles, monuments, and historical landmarks. The city's proximity to the sea allows for enjoyable activities such as windsurfing, while the friendly locals and vibrant culture add to the overall atmosphere. Newport is also known for its beautiful gardens, perfect for relaxation and rejuvenation. After a day of outdoor adventures, visitors can unwind at a local bar and immerse themselves in the lively atmosphere. Whether you're seeking history, nature, or a taste of local culture, Newport has it all.

  • The peak season is from June to August
  • The off-peak season is from October to December
  • Travelers tend to stay 3 days in Newport

6. Plan your dream getaway to Seaview

Seaview in England's United Kingdom offers a delightful outdoor vacation experience. With its stunning geography, including islands, a beautiful sea, and lush forests, it's the perfect destination for boating enthusiasts and beach lovers. The luxurious and romantic atmosphere is ideal for those seeking a tranquil getaway. Explore the local bars and gardens, and immerse yourself in the breathtaking scenery. Seaview is a haven for travelers looking for destination activities and a wide range of things to do. Whether you're seeking adventure or relaxation, Seaview has something for everyone.

  • The peak season is from June to August
  • The off-peak season is from October to December

5. Escape to Bembridge with a vacation package

Bembridge is a charming coastal town in England's Isle of Wight, offering a perfect outdoor vacation experience. With its beautiful beaches and sunny weather, visitors can enjoy various outdoor activities like boating and exploring the surrounding islands. The town also boasts a rich historical heritage, with historical landmarks and museums showcasing its cultural significance. Bembridge is known for its peaceful and relaxing atmosphere, making it an ideal destination for those seeking a break from city life. The town's gardens and scenic coastal landscapes add to its appeal, providing a serene environment for nature lovers.

  • Travelers tend to stay 4 days in Bembridge

Things to do in Isle of Wight

The Isle of Wight offers a perfect blend of outdoor adventure and stunning scenery for your vacation. Enjoy hiking trails, coastal walks, and recreational areas, along with camping opportunities. Don't miss nearby attractions and affordable adventures that add excitement to your trip, including a thrilling wild west showdown. Embrace the natural beauty and activities that make this island a fantastic getaway.

Shopping

House of Chilli offers a unique shopping experience with a variety of gourmet gifts and spicy products, perfect for souvenirs. Located in the heart of the Isle of Wight, it's a must-visit for food enthusiasts looking to take a taste of the island home.

Recreation

At Seaclose Park, enjoy serene walks amidst nature and participate in yoga sessions that promote relaxation. Shanklin Theatre offers a cultural escape with captivating performances, perfect for family entertainment. For a touch of luxury, the Royal London Yacht Club provides exclusive experiences in a stunning waterfront setting.

Adventure

The Isle Of Wight Coastal Footpath offers breathtaking views as you hike along its scenic trails, perfect for outdoor enthusiasts. Experience the thrill of Butterfly Paragliding, soaring through the skies with stunning landscapes beneath you. The Newport-Cowes Trail is ideal for outdoor adventures, inviting exploration through picturesque surroundings.

Nightlife

The Isle of Wight boasts a vibrant nightlife with options for everyone. Enjoy cocktails at The Piano Bar in Ryde, or dance the night away at Club 7 in Newport. For live music, check out The Cow in Cowes for local bands and a fun atmosphere.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in Isle of Wight

The Isle of Wight offers an ideal getaway for outdoor enthusiasts, featuring beautiful beaches, charming churches, and serene nature reserves. Visitors can immerse themselves in the local culture while enjoying various outdoor activities, making it perfect for those seeking adventure and scenic views. Whether you're planning a holiday filled with beach time or exploring unique points of interest, the Isle of Wight promises a memorable vacation experience for all travelers.

  • Osborne House: Step into the opulent summer retreat of Queen Victoria and Prince Albert. This stunning historic estate showcases exquisite architecture, lush gardens, and a fascinating glimpse into royal life. Explore the grand rooms and the beautiful grounds that overlook the Solent.
  • Cowes Harbour: Experience the charm of this picturesque harbor known for its vibrant sailing scene. Enjoy scenic views as yachts glide through the water, relax on the beach, or indulge in fresh seafood at waterfront restaurants.
  • Shanklin Old Village: Wander through this enchanting historic village, characterized by thatched cottages and quaint shops. Immerse yourself in local culture, enjoy traditional tea rooms, and take in the beautiful gardens that make this area truly special.

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 February and November) 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.

Find the Best Isle of Wight Vacation Packages

Isle of Wight Essential Information

Language
English
Currency
British pounds sterling
Closest Airport
Southampton Airport (SOU)

Isle of Wight Hotel Deals

Royal Esplanade Hotel

Royal Esplanade Hotel

16 The Esplanade Ryde England
Fully refundableReserve now, pay when you stay
$114 nightly
$137 total
Sep 30 - Oct 1
Total with taxes and fees
8/10 Very Good! (1,000 reviews)
"The property was well situated for the town and other amenities,but we had a Seaview and was very noisy,but staff accommodated us and we changed the room."

Reviewed on Sep 10, 2026

Royal Esplanade Hotel
The Birdham Hotel & Restaurant

The Birdham Hotel & Restaurant

1 Steyne Rd Bembridge England
Fully refundableReserve now, pay when you stay
$91 nightly
$109 total
Oct 18 - Oct 19
Total with taxes and fees
9.4/10 Exceptional! (111 reviews)
"This hotel is very clean throughout. The housekeeping team amazing, the room looked immaculate upon return each day. The staff are all very friendly. The food is very good and presented well. The only criticism is the evening menu choice is very limited and static"

Reviewed on Sep 20, 2026

The Birdham Hotel & Restaurant
Channel View Hotel

Channel View Hotel

4-8 Royal Street Sandown England
$46 nightly
$55 total
Oct 7 - Oct 8
Total with taxes and fees
5.6/10 (57 reviews)
"I was worried by the negative reviews of this hotel before arriving but circumstances dictated that we would stay here. In fact, the place was actually better than expected - not great but acceptable provided you only need the basics. Yes, the property is tired and in need of a face-lift; the carpets ..."

Reviewed on Sep 23, 2026

Channel View Hotel
See all 1,995 properties in Isle of Wight
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 vacation package cost?
From as low as $1,661. Yes, you read that right. Our Isle of Wight packages are a simple way to make your budget last longer. Combine your favorite hotels, flights and rental car and get out and explore this fabulous destination.
How do I get a cheap travel package to Isle of Wight?
Simply by bundling. Hotels, rental cars and flights — combine whatever you need into an Isle of Wight vacation package and save. Score even more discounts when you include extras such as sightseeing tours to your booking. But that's not the only good part. You have the flexibility to put together your vacation your way. We offer more than 550 airlines and 1,000,000 hotel options all over the world, so that everyone has a chance to travel and fulfill those vacation dreams.
How far in advance should I book my Isle of Wight vacation?
It can be tricky to know when is the perfect time to book your vacation to Isle of Wight. But typically the earlier you book, the better the prices. Sometimes, you can secure your flights and hotels nearly a year prior to departure. If you're thinking of a last-minute getaway, no need to worry! There are fabulous deals popping up on Expedia all the time.
What does an Expedia Isle of Wight travel package include?
With Expedia, you can select a combination of car rentals, flights and hotels to create your perfect Isle of Wight package. Once you've made your booking, you can add on the fun things like activities and tours. Don't forget — the more you bundle, the more you stand to save!
What should I know before booking an Isle of Wight travel package?
Locking in all the parts of your escape together is a great way to save. Combine your airfares, rental cars and hotels into a neat little package. But hotels aren't your only option. Expedia features all types of properties, including vacation rentals like oceanfront condos and serviced residences. The list goes on!
Can I choose my airline with an Isle of Wight Expedia vacation package?
Yes — that's one of the best things about an Expedia vacation package. You get to decide. We have more than 550 airline partners globally, so you have lots of choice when putting together your Isle of Wight adventure.
Does Expedia offer Book Now, Pay Later Isle of Wight vacation packages?
Thanks to our proud partnership with online lender Affirm, you can Book Now, Pay Later. You can tailor your trip with Expedia packages, so why not customize your payment arrangement too?
If I'm not able to travel, can I cancel my Isle of Wight vacation package?
Whether it's your flight or hotel, you can cancel or alter it. Booked your Isle of Wight vacation package in the last 24 hours? You may be able to make changes or cancellations for free. For older bookings, you may incur a fee from your hotel, airline or car rental company. For more details, take a look at our Customer Service Portal. We're here to help you every step of the way.

Stay near popular Isle of Wight attractions

A green building with a white porch and a sign that reads "Beach Cafe."
Photo by Tom Leeson

Osborne House

9.6/10 (76 reviews)
Find out about the history of East Cowes when you take a trip to Osborne House. Stroll along the area's seaside, or simply savor its lively bars.
See properties
A beach with a wooden walkway, pebbles, and a distant cliff.
Photo by Andrew Fry

Shanklin Beach

9.0/10 (206 reviews)
Why not spend a carefree afternoon at Shanklin Beach during your travels in Shanklin? Wander the seaside and picturesque gardens in this quaint area.
See properties
A beach with colorful beach huts, a lighthouse, and rocky breakwaters.
Photo by Steven Barker

Ventnor Beach

9.0/10 (37 reviews)
If a restful vacation is part of your travel plans, Ventnor Beach might be the perfect place to seek out during your trip to Ventnor. Wander the gardens and seaside in this quaint area.
See properties
A grassy field with a large sign reading "FESTIVAL" and several flags.
Photo by Tom Leeson

Seaclose Park

8.0/10 (2 reviews)
Explore the great outdoors at Seaclose Park, a lovely green space in Newport. Wander the beautiful beaches and seaside in the area.
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A traditional building with a thatched roof, named 'Pencil Cottage,' featuring a shop and a tea garden.
Photo by Angela Newlands

Shanklin Old Village

9.0/10 (148 reviews)
Find out about the history of Shanklin when you spend time at Shanklin Old Village. Wander the beautiful beaches and seaside in this relaxing area.
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An interior view of a large, industrial structure with a series of concrete pillars and beams, creating a geometric pattern.
Photo by Mike Campbell

Sandown Beach

8.8/10 (100 reviews)
Why not spend a carefree afternoon at Sandown Beach during your travels in Sandown? Visit the area's spas, or simply enjoy its coffeehouses.
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Isle of Wight Zoo

8.4/10 (29 reviews)
See the exotic and native animals who live at Isle of Wight Zoo during your travels in Sandown. Wander the beautiful beaches and seaside in the area.
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Isle of Wight Steam Railway

9.0/10 (16 reviews)
You can study the exhibits at Isle of Wight Steam Railway, a museum with a story of its own, during your travels to Havenstreet and Ashey. Wander the area's beautiful beaches or simply enjoy one of its lively bars.
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What to do in Isle of Wight

Portsmouth: Spinnaker Tower Ticket

Portsmouth: Spinnaker Tower Ticket

$26
per adult
80% of travellers recommend
Portsmouth: Spinnaker Tower Ticket
Portsmouth Historic Dockyard Ticket

Portsmouth Historic Dockyard Ticket

$62
per adult
100% of travellers recommend
Portsmouth Historic Dockyard Ticket
Iconic Spinnaker Tower, Portsmouth

Spinnaker Tower Portsmouth All Day Admission Ticket

$26
per adult
Spinnaker Tower Portsmouth All Day Admission Ticket
See all activities in Isle of Wight
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.