Pilot Point Vacation Packages 2026 from $296

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The Latest Pilot Point 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 23 hours 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 19 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 23 hours 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 2 hours ago

Roundtrip non-stop flight included

New York (NYC) to Salisbury (SBY)

9.4/10 Exceptional! (9 reviews)

Where to stay in Pilot Point

Find the best Pilot Point areas and neighborhoods for the activities you enjoy most. Learn more about Pilot Point

A marina at sunset with boats docked and an American flag visible.

Historic District

1 out of top 10 points of interest in this area

If you're spending some time in Historic District, Lewes Historic Complex and Preservation Forge are top sights worth seeing.

A lighthouse silhouette at sunset with rays of sunlight piercing through clouds, and a person paddling a kayak in the foreground.

Villages of Five Points

If you're looking for some top things to see and do in Villages of Five Points and surrounding area, you can visit Midway Speedway and Savannah Beach.

Wolfe Runne

While there might not be top attractions in Wolfe Runne, you can explore the larger area and discover places like Cape May - Lewes Ferry and Lewes Beach.

A red and white lighthouse on a rocky outcrop with calm water in the foreground and a clear sky.

Plantations East

Plantations East might not have many top sights, but Midway Speedway and Junction and Breakwater Trail are two attractions nearby that you can check out.

Love Creek

If you're looking for some top things to see and do in Love Creek and surrounding area, you can visit Tanger Outlets and Jungle Jim's River Safari Water Park.

Pilot Point Hotel Deals

Henlopen Oceanfront Hotel

511 North Boardwalk Rehoboth Beach DE

$119 nightly

$132 total

Oct 1 - Oct 2

Total with taxes and fees

8.6/10 Excellent! (1,939 reviews)

"5 stars all around. Great and helpful staff, clean facilities, rooms. Homerun!"

Reviewed on Sep 4, 2026

Beach Boutique Hotel

19953 Shuttle Road Rehoboth Beach DE

Fully refundableReserve now, pay when you stay

$89 nightly

$99 total

Oct 1 - Oct 2

Total with taxes and fees

La Mer Beachfront Resort

1317 Beach Avenue Cape May NJ

$175 nightly

$201 total

Oct 4 - Oct 5

Total with taxes and fees

9/10 Wonderful! (1,080 reviews)

"All around great place, location and service!!"

Reviewed on Aug 31, 2026

See all 6,765 properties in Pilot Point

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.