Isle of Wight Vacations from $1,423

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The Latest Isle of Wight vacation packages

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

Miramar Condominiums

Downtown Ocean City

$1,423

per person

Nov 25 - Nov 29

found 1 day ago

Roundtrip non-stop flight included

Akron (CAK) to Salisbury (SBY)

9.4/10 Exceptional! (33 reviews)

Sea Bay Hotel

Midtown Ocean City

Save 100% on your flight

$2,216

per person

Nov 21 - Nov 26

found 1 day ago

Roundtrip flight included

San Juan (SJU) to Salisbury (SBY)

8.2/10 Very Good! (673 reviews)

Beach Walk

Downtown Ocean City

$2,225

per person

Nov 25 - Nov 29

found 1 day ago

Roundtrip non-stop flight included

Akron (CAK) to Salisbury (SBY)

7.8/10 Good! (115 reviews)

The Shore House

West Ocean City

$2,132

per person

Nov 26 - Nov 30

found 1 day ago

Roundtrip non-stop flight included

San Juan (SJU) to Salisbury (SBY)

6.6/10 (782 reviews)

Inn at Perry Cabin

Downtown St. Michaels

$1,784

per person

Nov 26 - Nov 29

found 2 hours ago

Roundtrip flight included

Philadelphia (PHL) to Salisbury (SBY)

9.6/10 Exceptional! (399 reviews)

It’s so lovely and elegant I almost don’t want to tell people it’s there. Stunning, perfect in every way.

Reviewed on Sep 8, 2026

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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.

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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.

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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.

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Isle of Wight Hotel Deals

Grand Hotel Ocean City Oceanfront

2100 N Baltimore Ave Ocean City MD

Fully refundableReserve now, pay when you stay

$94 nightly

$106 total

Oct 14 - Oct 15

Total with taxes and fees

9/10 Wonderful! (3,887 reviews)

"Outdoor pool was very cold."

Reviewed on Sep 19, 2026

Fenwick Inn

13801 Coastal Highway Ocean City MD

Fully refundableReserve now, pay when you stay

$82 nightly

$92 total

Sep 20 - Sep 21

Total with taxes and fees

Princess Royale Oceanfront Resort

Oceanfront on 91st Street Ocean City MD

$108 nightly

$119 total

Oct 18 - Oct 19

Total with taxes and fees

8.8/10 Excellent! (2,767 reviews)

"Wonderful location! Loved the beachfront bar!"

Reviewed on Sep 19, 2026

See all 9,996 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.