Isle of Wight Vacation Packages

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Top Isle of Wight Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5
Price was CA $1,544, price is now CA $1,319 per person
CA $1,319
per person
Dec 23 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Salisbury (SBY)
9.4/10 Exceptional! (874 reviews)
Fantastic experience. Top rate hotel. One of the best we have ever visited.

Reviewed on Nov 3, 2026

Beach Walk

Beach Walk

2 out of 5
Downtown Ocean City
Price was CA $6,216, price is now CA $4,521 per person
CA $4,521
per person
Dec 23 - Dec 30
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Salisbury (SBY)
7.6/10 Good! (128 reviews)
We never slept here. The room was incredibly dirty. Stained sheets, stained carpet, god only knows what on the walls in the bathroom. The table and chairs were a table that folded out from the wall with a stick underneath. The chairs were two rusty folding chairs. The blinds in the window were busted up and only covered half the window. I honestly don’t know how they’ve not been shut down. We quickly found another hotel.

Reviewed on Oct 13, 2026

Oceanic Motel

Oceanic Motel

2 out of 5
Downtown Ocean City
Price was CA $6,316, price is now CA $4,964 per person
CA $4,964
per person
Dec 23 - Dec 30
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Salisbury (SBY)
7/10 Good! (848 reviews)

Boardwalk One

Boardwalk One

3 out of 5
Downtown Ocean City
Price was CA $1,613, price is now CA $1,334 per person
CA $1,334
per person
Dec 23 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Salisbury (SBY)
7.4/10 Good! (179 reviews)

The Shore House

The Shore House

2 out of 5
West Ocean City
Price was CA $5,826, price is now CA $5,020 per person
CA $5,020
per person
Dec 23 - Dec 30
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Salisbury (SBY)
6.6/10 (840 reviews)

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Isle of Wight Hotel Deals

Holiday Inn & Suites Ocean City by IHG

Holiday Inn & Suites Ocean City by IHG

3 out of 5
1701 Atlantic Avenue Ocean City MD
Fully refundable
The price is CA $126 per night from Dec 2 to Dec 3
CA $126
CA $141 total
Dec 2 - Dec 3
includes taxes & fees
9.4/10 Exceptional! (1,461 reviews)
"The oceanfront views were absolutely spectacular and easily one of the highlights of our stay! The bed and linens were incredibly comfortable, and the food was delicious. There were a few areas that could use improvement. The shower/tub combination was difficult to get in and out of, and the shower ..."

Reviewed on Nov 3, 2026

Holiday Inn & Suites Ocean City by IHG
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
Oceanfront on 91st Street Ocean City MD
The price is CA $122 per night from Nov 8 to Nov 9
CA $122
CA $159 total
Nov 8 - Nov 9
includes taxes & fees
8.8/10 Excellent! (2,891 reviews)
"My great niece and I had an overnight girls trip, we had a great time. Loved our room and frint desk person was so friendly"

Reviewed on Nov 4, 2026

Princess Royale Oceanfront Resort
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
2100 N Baltimore Ave Ocean City MD
Fully refundableReserve now, pay when you stay
The price is CA $90 per night from Nov 5 to Nov 6
CA $90
CA $101 total
Nov 5 - Nov 6
includes taxes & fees
9/10 Wonderful! (3,988 reviews)
"Excellent experience this past weekend at the Grand! We enjoyed our stay immensely! Thank you"

Reviewed on Nov 4, 2026

Grand Hotel Ocean City Oceanfront
See all 9,634 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.
All Inclusive Vacations
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Beach Vacations
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Stay near popular Isle of Wight attractions

beach near Smokehouse Cove

Why not spend a lazy afternoon at beach near Smokehouse Cove during your trip to Bishopville? Wander the marina and beaches while you're in the area.
See properties

Frequently asked questions

How much does an Isle of Wight vacation package cost?
Cross off another part of the world with our Isle of Wight vacation packages, which start from a low CA $1,319. Pick the hotels and flights that suit your plans. Then, add on one or two activities or tours to round off your unique adventure.
How do I get a cheap travel package to Isle of Wight?
Browse and lock in everything in the one place with our Isle of Wight vacation packages. We have incredible bargains on hotels, flights and more that'll keep your pocketbook happy and your adventurous spirit alive. And, with more than 550 partner airlines and 1,000,000 hotels around the globe to choose from, you have countless opportunities to mix and match all you want.
How far in advance should I book my Isle of Wight vacation?
Savvy travelers will likely want to reserve their seats as early as possible. You can usually browse through international airfares on Expedia up to 12 months before your flight. If you're purchasing your ticket at the last minute, fear not. Low prices occasionally appear just weeks before departure.
What does an Expedia Isle of Wight travel package include?
Flights, hotels and a cool car for all your fun road trip adventures. Simply pick and choose your preferred bundle and get access to incredible deals. Once you've made your booking, add on a couple of sightseeing tours and watch your savings stack up. When it comes to crafting your Isle of Wight vacation, you're the boss!
What should I know before booking an Isle of Wight travel package?
A travel package can be tailored to your budget and is a fantastic way to make your money go further. How little or much you include is completely up to you. Hotels, rental cars and flights — come up with a combination that suits your plans.
Can I choose my airline with an Isle of Wight Expedia vacation package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines worldwide. Our packages give you the freedom to take your pick of available flights, hotels and activities that fit your needs.
If I'm not able to travel, can I cancel my Isle of Wight vacation package?
Yes you can, and we're here to help. You may be able to cancel and rebook your Isle of Wight vacation package at no cost if you booked in the last 24 hours. But you may incur a fee from your hotel, airline or car rental company if your booking is older than that. If life throws you a curveball, have a look at our Customer Service Portal for further information.

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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.