Isle of Wight Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Isle of Wight Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Grand Hotel Ocean City Oceanfront
Downtown Ocean City
CA $992
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Salisbury (SBY)
9/10 Wonderful! (3,946 reviews)
No breakfast and paid parking. And horrible water pressure the 10.00 a day for parking crazy to many options on the boardwalk
View was awesome. Bad everything is extra
Reviewed on Oct 16, 2026
Saint Tropez
North Ocean City
CA $1,000
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Salisbury (SBY)
9.2/10 Wonderful! (158 reviews)
Minus the Nor’Eastern it was a perfect weekend. We were locked out once but they after hours desk helped within minutes. Perfect location. Absolutely will be back.
Reviewed on Oct 9, 2026
Ready to book your vacation to Isle of Wight?
Isle of Wight Hotel Deals
Castle in the Sand
3701 Atlantic Avenue Ocean City MD
CA $107
CA $120 total
Oct 18 - Oct 19
includes taxes & fees
Grand Hotel Ocean City Oceanfront
2100 N Baltimore Ave Ocean City MD
Fully refundableReserve now, pay when you stay
CA $91
CA $102 total
Nov 1 - Nov 2
includes taxes & fees
9/10 Wonderful! (3,959 reviews)
"No breakfast and paid parking. And horrible water pressure the 10.00 a day for parking crazy to many options on the boardwalk View was awesome. Bad everything is extra"
Reviewed on Oct 16, 2026
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.
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.
beach near Poplar Point
Why not spend a lazy afternoon at beach near Poplar Point during your trip to Bishopville? Wander the marina or discover the area's sunsets.
beach near Isle Of Wight Wildlife Management Area
Why not spend a lazy afternoon at beach near Isle Of Wight Wildlife Management Area during your trip to Bishopville? Wander the marina and beaches while you're in the area.
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 $992. 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.
Explore a world of travel with Expedia
- All Inclusive Resorts and in Ocean City
- Comfort Inn Ocean City Boardwalk
- Renovated Sherwood West Condo | Balcony & 4 Flat-Screen TVs | 400’ to Beach
- Ochg 6 10th Street Bottom
- 1/2 Mi to Ocean City Beach! Poolside Retreat
- Alexander Mini Mansion 203C by Seaside Vacations & Sales
- Amazing Suite in Oceanside Building w/Shared Pool, Private Washer/Dryer, WiFi
- Towers 1003
- Hotels with Free Breakfast in Ocean City
- ⭐️Luxury Belmont Towers 402 Direct Ocean Front Pool Gym⭐️
- Fountainhead 209 1 Bedroom Condo by RedAwning
- Large & Beautiful Vacation Suite w/Balcony Bay Views, Shared Pool, Central AC
- Cheap Hotels in Ocean City
- Golf Hotels in Ocean City
- Barge Road 136o9 3 Bedroom Home by RedAwning
- ** Select 2023 weeks have been discounted by $200.00! Prices shown include discount. **<br>2 br/2 bath Antigua / outdoor pool/Ofront bldg
- The Light of Seabright Your luxury retreat in OC. Walking distance to Boardwalk!
- Roomy Townhouse
- Family Hotels in Ocean City
- The Shore House
- Hotels near Ocean City Boardwalk
- Midtown Ocean City Hotels
- End
- 3 Bedroom Ocean Block Condo at Seaside Retreat just Steps from the Beach!
- Beautiful Sunset Get Away
- Oceanfront townhome w/ Outdoor Pool by Seaside Vacations & Sales
- Motels in Ocean City
- Hampton Inn & Suites Ocean City/Bayfront
- Spacious Home w Parking Steps to Beach Boardwalk Concerts Festivals.
- Hotels with Free Breakfast in Montego Bay
- Bridge Point I 26 | Condo in Ocean City
- Hilton Garden Inn Ocean City Oceanfront
- Sea Watch 1319
- Rainbow 1109
- Adults Only Resorts & in Sunset Island
- 2 Bedroom Condo with Outdoor Rooftop Pool
- Sunburstparadise
- Salty Sands I 402
- Luxury Hotels in Ocean City
- Beach Hotel Hotels in Ocean City
- Romantic Hotels in Ocean City
- Condo Rentals in Ocean City
- Ocean City Hotels
- Direct Oceanfront condo in midtown Ocean City
- Beach Hotel Hotels in Heron Harbour Isle
- Romantic Beach Getaway For 2 In Ocean City MD
- Barefoot Country 304 1 Bedroom Condo by RedAwning
- Beautiful condo steps from the beach by Seaside Vacations & Sales
- Oceanfront Hotels in Midtown Ocean City
- B&B in Ocean City
- Calypso unit 602
- Hotels near Ocean Plaza Mall Shopping Center
- Cozy 1br cabin @ Beach Bum West
- Gorgeous Side Ocean View From Your Private Balcony
- Oceanfront Hotels in Glen Riddle
- El Capitan
- North Ocean City Hotels
- Edgewater Retreat
- Air-Conditioned Condo 1 Block from the Beach w/ Balcony, W/D & Shared Pool
- Oceanfront Hotels in Ocean City
- Diamond Beach 414 3 Bedroom Condo by RedAwning
- Sandpiper Dunes 406 by Seaside Vacations & Sales
- Two-Story penthouse condo with spacious balcony, pool, & incredible views
- Pet-Friendly Hotels in Ocean City
- Ocean FRONT Gem w/Pools
- Beautiful & CLEAN! Waterfront condo with epic sunsets and a POOL!
- Royal Hawaiian 401
- Oceanfront Penthouse w/ Tons of Space and a Pool
- Luxury Townhome with Pool
- Spa Hotels in Ocean City
- Beautiful 4th-Floor Condo in Oceanfront Complex w/Beach Views & Shared Pool
- Hotels with Kitchenettes in Ocean City
- Ochg Seafoam 1005 Sum
- Ashore Oceanfront Hotel by Marriott
- Ocean City Beach
- Museum of Eastern Shore Culture at Salisbury University
- Berlin Vacations
- Casino at Ocean Downs
- River Run Golf Club
- Ocean City Boardwalk
- Trimper's Rides
- Vienna Vacations
- Ocean City Vacations
- Long Wharf Park
- Jolly Roger at the Pier
- Main Street Berlin
- Midway Shopping Center
- Visit North Ocean City
- Visit Ocean City
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
