Isle of Wight Vacations from $296

Book a Hotel + Flight or Car together to unlock savings

Plan, book, travel with confidence
Better together
Save up to $2,000 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

The Latest Isle of Wight vacation packages

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

The Lodge at Great Oak Landing

$296

per person

Oct 30 - Nov 1

found 1 day ago

Roundtrip flight included

Orlando (MCO) to Salisbury (SBY)

8/10 Very Good! (103 reviews)

Gem of a local place on the water. The rooms are big and the beds are soooo comfy. The pool is cute and the beach has bands on weekends. There are gas grills and a decent restaurant. It's not fancy (for fancy stay at the manor next door). But it's not corporate either. It's authentic, peaceful and fun.

Reviewed on Aug 30, 2026

The Shore House

West Ocean City

$1,192

per person

Oct 30 - Nov 1

found 21 hours ago

Roundtrip flight included

Orlando (MCO) to Salisbury (SBY)

6.6/10 (766 reviews)

Sea Bay Hotel

Midtown Ocean City

$1,568

per person

Nov 20 - Nov 22

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)

8.2/10 Very Good! (663 reviews)

Miramar Condominiums

Downtown Ocean City

$1,637

per person

Oct 22 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) to Salisbury (SBY)

9.4/10 Exceptional! (31 reviews)

Beautiful house and clean rooms! Perfectly equipped with everything!

Reviewed on Aug 28, 2026

OCHG Beachviews

Downtown Ocean City

$1,030

per person

Oct 22 - Oct 26

found 4 hours ago

Roundtrip non-stop flight included

New York (NYC) to Salisbury (SBY)

9.4/10 Exceptional! (9 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Isle of Wight

View all trips

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

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.

See properties

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.

See properties

Isle of Wight Hotel Deals

Princess Royale Oceanfront Resort

Oceanfront on 91st Street Ocean City MD

$115 nightly

$127 total

Oct 4 - Oct 5

Total with taxes and fees

Grand Hotel Ocean City Oceanfront

2100 N Baltimore Ave Ocean City MD

Fully refundableReserve now, pay when you stay

$97 nightly

$109 total

Oct 5 - Oct 6

Total with taxes and fees

Fenwick Inn

13801 Coastal Highway Ocean City MD

Fully refundableReserve now, pay when you stay

$84 nightly

$95 total

Sep 21 - Sep 22

Total with taxes and fees

8.8/10 Excellent! (2,107 reviews)

"Great"

Reviewed on Sep 5, 2026

See all 10,009 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.