Pilot Point Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Pilot Point

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

Beach Walk

2 out of 5
Downtown Ocean City
per person
Sep 12 - Sep 14
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
7.6/10 Good! (65 reviews)
We stayed one night at Beach Walk and it was a nice experience overall. It was great to be right by the OC boardwalk, where we could access dining, shopping, and the beach. Our room was clean and the beds were comfortable. We were lucky to get a parking spot in the small lot right next to the building. The only complaints I have- the blinds on the window by my bed were kind of messed up and the curtains were incredibly sheer. I could have used more darkness. Also, at the top of the stairs outside the floor where we stayed, the carpet was ripped. I tripped and skinned my knee. Hopefully that is fixed soon.

Reviewed on Jul. 26, 2025

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
per person
Sep 12 - Sep 14
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
9/10 Wonderful! (2,980 reviews)
The staff was very friendly. The food was good and the location was excellent. It’s always nice to have access to parking with your hotel room. I would definitely recommend it

Reviewed on Jul. 27, 2025

Ocean 1 Hotel and Suites

Ocean 1 Hotel and Suites

2 out of 5
Downtown Ocean City
per person
Sep 12 - Sep 14
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
8/10 Very Good! (608 reviews)
Front daek was very kind and polite

Reviewed on Jul. 24, 2025

Americana Motor Inn

Americana Motor Inn

2.5 out of 5
Downtown Ocean City
per person
Sep 12 - Sep 14
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
8.4/10 Very Good! (772 reviews)
Great clean rooms right off the boardwalk. Staff is always very helpful.

Reviewed on Jul. 28, 2025

Princess Bayside Beach Hotel

Princess Bayside Beach Hotel

2.5 out of 5
Midtown Ocean City
per person
Sep 12 - Sep 14
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
7.8/10 Good! (1,001 reviews)
Quick walk to the ocean front. Plenty of parking.

Reviewed on Jul. 27, 2025

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
Lewes which includes signage and a park

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.

Find hotels in Historic District

Pilot Point Hotel Deals

Henlopen Oceanfront Hotel

Henlopen Oceanfront Hotel

2 out of 5
511 North Boardwalk, Rehoboth Beach, DE
The price is CA $411 per night from Jul 31 to Aug 1
CA $411
CA $456 total
Jul 31 - Aug 1
includes taxes & fees
8.4/10 Very Good! (1,577 reviews)
"Great property. Recently renovated rooms from what I heard & the rooms were very nice. Our bathroom had a tub and a shower, so that was nice to be able to both be able to shower at the same time. Parking is TIGHT! If you have a huge truck or SUV, don’t bring it. We JUST fit with a suburban. I saw ..."

Reviewed on Jul. 26, 2025

Henlopen Oceanfront Hotel
Staybridge Suites Rehoboth Beach by IHG

Staybridge Suites Rehoboth Beach by IHG

2 out of 5
34521 Old Postal Lane, Rehoboth Beach, DE
Fully refundable
The price is CA $271 per night from Aug 24 to Aug 25
CA $271
CA $301 total
Aug 24 - Aug 25
includes taxes & fees
9.4/10 Exceptional! (159 reviews)
"I am beyond grateful for a wonderful birthday weekend at Staybridge! I am sure it was fully booked, or close to it. The room was exceptional. The bedding was CRISP WHITE, not one spot! Super clean, amazing kitchen and space for our family. Big shout out to the breakfast staff. The kind and patient ..."

Reviewed on Jul. 27, 2025

Staybridge Suites Rehoboth Beach by IHG
The Breakers Hotel & Suites

The Breakers Hotel & Suites

2.5 out of 5
105 Second Street, Rehoboth Beach, DE
The price is CA $309 per night from Jul 31 to Aug 1
CA $309
CA $350 total
Jul 31 - Aug 1
includes taxes & fees
8.8/10 Excellent! (1,890 reviews)
"The Breakers was a great hotel to stay for a weekend trip. The property was generally clean and well maintained. The rooms were also very clean and the bed was comfortable. We really enjoyed having a balcony and sitting outside at the end of the night before bed. The air conditioner kept the room ..."

Reviewed on Jul. 26, 2025

The Breakers Hotel & Suites
See all 7,372 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Pilot Point vacation package cost?
From just CA $1,091. Yes, you read that correctly. Our Pilot Point vacation packages are an easy way to make your dollar go further. Combine your hotels, flights and rental car and get out and see this lively destination.
How do I get a cheap travel package to Pilot Point?
By bundling. Hotels, flights and rental cars — combine whatever you need into a Pilot Point vacation package to save tons of cash. Score even more deals when you include extras such as day tours to your booking. But that's not the only good part. You have the flexibility to customize your vacation your way. We offer more than 550 partner airlines and 1,000,000 hotel options in all corners of the globe, so that everyone has a chance to travel and live out those vacation fantasies.
What are the top hotels in Pilot Point?
If it's comfort and convenience you're searching for, you can't go past 10 Texas - Perfect Beach Cottage For Your Lewes Vacation. Spend your nights unwinding here and your days wandering around Pilot Point's best attractions.
How far in advance should I book my Pilot Point vacation?
Reserving your tickets early with Expedia means one less thing to worry about. Many air carriers advertise tickets up to 12 months prior to take off. This is generally the cheapest time to book. If circumstances have left you booking late, last-minute deals to Pilot Point will sometimes occur just weeks before departure.
What does an Expedia Pilot Point travel package include?
It comes down to what you want. If you're traveling by yourself, you might decide to combine hotels and flights. Taking the whole crew to Pilot Point? A travel package including hotels, flights and rental cars might be a better fit. Expedia gives you the freedom to customize your travel package.
What should I know before booking a Pilot Point travel package?
A travel package can be customized for your circumstances and is a fantastic way to make your budget go further. What you include is totally up to you. Rental cars, hotels and flights — choose any combination that suits your plans.
Can I choose my airline with a Pilot Point Expedia vacation package?
Expedia offers access to more than 550 partner airlines worldwide, so you sure can! Just select the carrier you want and craft your ideal Pilot Point getaway.
If I'm not able to travel, can I cancel my Pilot Point vacation package?
We totally get that life doesn't always go according to plan. If you've locked in a Pilot Point vacation package and have to cancel or amend it, we can help. We recommend checking out our Customer Service Portal first for information. But generally speaking, if you've booked your package in the last 24 hours, you may be able to cancel or change your itinerary at no cost. If it's been more than 24 hours, your airline, hotel or car rental company may impose a charge.

Discover the most popular places to visit in Pilot Point

Lewes Beach featuring a lighthouse, a beach and general coastal views

Lewes Beach

Sandwiched between Delaware Bay and the town of Lewes is mile after mile of white sand that attracts beachcombers and sunbathers.

Lewes Beach
Cape May - Lewes Ferry

Cape May - Lewes Ferry

Explore the waterfront in Lewes with a trip to Cape May - Lewes Ferry. Wander the beautiful beaches and seaside in this family-friendly area.

Cape May - Lewes Ferry

Nassau Valley Winery

You can enjoy a tasting or tour at Nassau Valley Winery during your travels to Lewes. Wander the beautiful beaches and seaside in this family-friendly area.

Nassau Valley Winery

Things to do

Bethany Beach Bash Scavenger Hunt

Bethany Beach Blitz Scavenger Hunt

CA $40
per adult
Bethany Beach Blitz Scavenger Hunt
See all activities in Lewes
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.