Pilottown Village Vacations from $663

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Your Pilottown Village Vacation

Get ready to experience Pilottown Village your way with a custom Pilottown Village vacation package! Uncovering the treasures of this city is made simpler with a base in a neighborhood such as Bay Vista, which is good for walking, among lots of other things. If taking in sights is on the to-do list during your trip to Pilottown Village, stop by top attractions like Lewes Beach, Cape Henlopen State Park and Cape Henlopen Beach. Whoever you're going away with and whatever you plan to spend, your ultimate Pilottown Village vacation is just a few clicks away with Expedia.

The Latest Pilottown Village vacation packages

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

Boardwalk One

3 out of 5
Downtown Ocean City
Price was $794, price is now $663 per person
$663
per person
Nov 1 - Nov 6
found 3 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
7.4/10 Good! (164 reviews)
Close to boardwalk, beach, shopping and dining. Also it was very affordable.

Reviewed on Sep 16, 2025

Beach Walk

Beach Walk

2 out of 5
Downtown Ocean City
Save 100% on your flight
Price was $2,045, price is now $1,572 per person
$1,572
per person
Dec 6 - Dec 9
found 8 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
7.6/10 Good! (87 reviews)
There was a funny smell in the hallway many times throughout the days. Bed was not in good shape

Reviewed on Aug 25, 2025

Bay Club Resort by Coolvacay

Bay Club Resort by Coolvacay

3 out of 5
Midtown Ocean City
Price was $1,190, price is now $938 per person
$938
per person
Nov 1 - Nov 6
found 3 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
8.2/10 Very Good! (38 reviews)
I loved the dock and the gorgeous sunsets .

Reviewed on Sep 7, 2025

Miramar Condominiums

Miramar Condominiums

2 out of 5
Downtown Ocean City
Price was $1,238, price is now $1,006 per person
$1,006
per person
Nov 1 - Nov 6
found 3 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
9.4/10 Exceptional! (15 reviews)
Stayed in unit 505 and it was beautiful! We loved it!

Reviewed on Aug 23, 2025

OCHG Ocean Block 7-11

OCHG Ocean Block 7-11

3 out of 5
Downtown Ocean City
Price was $1,195, price is now $975 per person
$975
per person
Nov 1 - Nov 6
found 3 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
8/10 Very Good! (3 reviews)
Don't see what you're looking for?
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Discover the most popular places to visit in Pilottown Village

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

Lewes Beach

4.5/5(363 reviews)

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

Lewes Beach
Leaving Lewes .

Cape May - Lewes Ferry

4.5/5(347 reviews)

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
Cape Henlopen Beach

Cape Henlopen Beach

4.5/5(5 reviews)

Why not spend a lazy afternoon at Cape Henlopen Beach during your trip to Lewes? Stroll along the beaches or visit the shops in the area.

Cape Henlopen Beach

What to do in Pilottown Village

Bethany Beach Bash Scavenger Hunt

Bethany Beach Blitz Scavenger Hunt

$23
per adult
Bethany Beach Blitz Scavenger Hunt
Radical Rehoboth Scavenger Hunt

Radical Rehoboth Scavenger Hunt

$29
per adult
80% of travellers recommend
Radical Rehoboth Scavenger Hunt
See all activities in Pilottown Village

Pilottown Village Hotel Deals

Henlopen Oceanfront Hotel

Henlopen Oceanfront Hotel

2 out of 5
511 North Boardwalk, Rehoboth Beach, DE
Fully refundableReserve now, pay when you stay
$96 nightly
The price is $107 total per night from Sep 28 to Sep 29
$107 total
Sep 28 - Sep 29
Total with taxes and fees
8.4/10 Very Good! (1,663 reviews)
"Great view great room friendly staff"

Reviewed on Sep 27, 2025

Henlopen Oceanfront Hotel
La Mer Beachfront Resort

La Mer Beachfront Resort

3.5 out of 5
1317 Beach Avenue, Cape May, NJ
$149 nightly
The price is $171 total per night from Oct 15 to Oct 16
$171 total
Oct 15 - Oct 16
Total with taxes and fees
9/10 Wonderful! (1,162 reviews)
"We had an ocean view renovated room and a partial view non renovated room for our college aged kids. Both were great, but the renovated room was much better ! The other one was spacious and clean too, just a bit dated. Staff was great, restaurant was great and we would stay here again!"

Reviewed on Sep 25, 2025

La Mer Beachfront Resort
The Breakers Hotel & Suites

The Breakers Hotel & Suites

2.5 out of 5
105 Second Street, Rehoboth Beach, DE
$95 nightly
The price is $105 total per night from Oct 26 to Oct 27
$105 total
Oct 26 - Oct 27
Total with taxes and fees
8.8/10 Excellent! (1,869 reviews)
"I have been staying at this hotel for over 20 years on and off. I have seen the changes Great accommodations at affordable prices and in the center of everything. VDP"

Reviewed on Sep 25, 2025

The Breakers Hotel & Suites
See all 7,228 properties in Pilottown Village
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.

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Frequently asked questions

How much does a Pilottown Village vacation package cost?
You'll find cheap prices from $663 on Expedia for your Pilottown Village escape. However, factors like the length of stay, hotel choice and season will determine how much your vacation to Pilottown Village costs.
What are the cheapest months to go to Pilottown Village?
If you're hoping to snag a cheap Pilottown Village vacation package, consider visiting in January, October and December. You'll usually find lower prices on airfares and hotels during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Pilottown Village?
With a well-planned itinerary, you can easily visit the main Pilottown Village attractions in a handful of days. But if you want to discover hidden spots or go on day trips, think about booking your Pilottown Village vacation for longer.
How to find the best Pilottown Village package deals?
Start your search for a Pilottown Village package deal by entering your travel dates and destination under our "Packages" tab. Then select some filters, like "Guest rating" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the perfect Pilottown Village package deal straight away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Pilottown Village getaway off to a flying start.
Is it cheaper to book a Pilottown Village vacation as a package?
You can enjoy significant savings on your Pilottown Village escape by booking a customized vacation package. Check the "Package" heading, then select your travel dates and destination to browse some great airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Pilottown Village?
If you're planning a spur-of-the-moment Pilottown Village trip, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land sensational deals on your flights and hotels by booking well in advance.
Does Expedia offer Book Now, Pay Later Pilottown Village vacation packages?
Your Pilottown Village getaway should be an escape from your busy life, not a source of money worries. So to allow you a bit more flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.