Port Penn Vacations from $290

Book a Hotel + Flight or Car together to unlock savings

Your Port Penn Vacation

From its highlights to its hidden delights, this city is best experienced with a Port Penn vacation package. Find a place to stay in Historical Old New Castle, which is good for walking, markets and history. Not sure what to see or do first during your trip to Port Penn? Check out famous attractions such as Frightland. Browse Expedia's wide range of travel options and book your dream vacation to Port Penn now.

The Latest Port Penn vacation packages

Price found within the past 48 hours. Click for updated prices.
Rio Hotel & Casino, a Destination by Hyatt Hotel

Rio Hotel & Casino, a Destination by Hyatt Hotel

4 out of 5
Price was $743, price is now $290 per person
$290
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Las Vegas (LAS)
7.6/10 Good! (6,408 reviews)
Welcoming staff, clean facilities (minus the smoke), and clean room. The smoking indoors took us off guard. We both smelled the smoke as soon as we walked in the doors.

Reviewed on Nov 1, 2025

Bentley Hotel South Beach

Bentley Hotel South Beach

4 out of 5
South Beach
Price was $2,381, price is now $1,040 per person
$1,040
per person
Dec 6 - Dec 13
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
9.4/10 Exceptional! (390 reviews)
Everything was perfect. I will recommend this hotel excellent.

Reviewed on Oct 28, 2025

The Shelborne By Proper, a Member of Design Hotels

The Shelborne By Proper, a Member of Design Hotels

4 out of 5
South Beach
Price was $2,444, price is now $1,073 per person
$1,073
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
9.8/10 Exceptional! (39 reviews)
Truly a five star experience from the vibe to the amenities to the service*****

Reviewed on Oct 28, 2025

Los Angeles Deluxe Suites - 2 Bedrooms & 2 Bathrooms

Los Angeles Deluxe Suites - 2 Bedrooms & 2 Bathrooms

4.5 out of 5
Hollywood
Price was $1,292, price is now $583 per person
$583
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip flight included
New York (JFK) to Los Angeles (LAX)
9.2/10 Wonderful! (78 reviews)
Beds were good altough the bed covers were stained everything else was good.

Reviewed on Jul 31, 2025

Westgate Flamingo Bay Resort

Westgate Flamingo Bay Resort

4 out of 5
Spring Valley
Price was $1,428, price is now $654 per person
$654
per person
Jan 12 - Jan 19
found 10 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Las Vegas (LAS)
8.8/10 Excellent! (1,003 reviews)
Very clean love the place I recommend!!!

Reviewed on Oct 20, 2025

Don't see what you're looking for?
See all available trips from Columbus to Port Penn
View all trips

Discover the most popular places to visit in Port Penn

Frightland

Enjoy an outing to Frightland during your stay in Middletown. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Frightland

Back Creek Golf Club

Enjoy a round of golf in Middletown at Back Creek Golf Club. While you're here, you can savor the top-notch restaurants.

Back Creek Golf Club

Frog Hollow Golf Club

Enjoy a round of golf in Middletown at Frog Hollow Golf Club. While in this family-friendly area, you can enjoy the restaurants.

Frog Hollow Golf Club

Port Penn Hotel Deals

DoubleTree by Hilton Downtown Wilmington - Legal District

DoubleTree by Hilton Downtown Wilmington - Legal District

4 out of 5
700 N King St, Wilmington, DE
Fully refundableReserve now, pay when you stay
$90 nightly
The price is $99 total per night from Nov 30 to Dec 1
$99 total
Nov 30 - Dec 1
Total with taxes and fees
7.2/10 Good! (1,003 reviews)
Breakfast buffet was excellent.

Reviewed on Oct 15, 2025

DoubleTree by Hilton Downtown Wilmington - Legal District
Quality Inn Newark - Wilmington

Quality Inn Newark - Wilmington

2.5 out of 5
65 Geoffrey Dr, Newark, DE
Fully refundableReserve now, pay when you stay
$53 nightly
The price is $59 total per night from Nov 21 to Nov 22
$59 total
Nov 21 - Nov 22
Total with taxes and fees
5/10 (1,011 reviews)
I was good for the value.

Reviewed on Oct 22, 2025

Quality Inn Newark - Wilmington
Sonesta Select Newark Christiana Mall

Sonesta Select Newark Christiana Mall

3 out of 5
48 Geoffrey Dr, Newark, DE
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $119 total per night from Nov 30 to Dec 1
$119 total
Nov 30 - Dec 1
Total with taxes and fees
7.6/10 Good! (1,141 reviews)
The staff were friendly and helpful. Rooms were clean and comfortable but there were crickets in the bathroom. Not sure how they were coming in but every time I killed one another one showed up (all weekend).

Reviewed on Oct 27, 2025

Sonesta Select Newark Christiana Mall
See all 437 properties in Port Penn
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.

Find the Best Port Penn Vacation Packages

Port Penn Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Philadelphia Intl. Airport (PHL)
Top Sights
Frightland, Back Creek Golf Club and Frog Hollow Golf Club

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Port Penn vacation package cost?
You can snap up a vacation package to this top destination from $290 on Expedia. However, how much your vacation to Port Penn costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Port Penn?
You can typically find lower rates and greater availability in November, December and January. Browse our cheap Port Penn vacation packages and you could land some great off-season deals.
How many days is enough for Port Penn?
Generally, a handful of days is enough to see the top sights during your Port Penn vacation. But if you want to have some time to unwind or go on day tours, think about extending your itinerary.
How to find the best Port Penn package deals?
Use Expedia's filter tool to help you find some great Port Penn package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or search for Port Penn package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
Is it cheaper to book a Port Penn vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging accommodations and flights separately. Better still, you can personalize your Port Penn getaway to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Port Penn?
If you have your Port Penn travel dates locked in, book as early as you can to grab some outstanding deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are ideal for traveling on a whim.
Does Expedia offer Book Now, Pay Later Port Penn vacation packages?
Jet off on your perfect trip to Port Penn with help from our Book Now, Pay Later vacations. There's no need to save like crazy or wait for payday — we've partnered with online lender Affirm to give you flexibility and choice. Our vacation packages with payment plans mean you can split the cost over 3, 6 or 12 months. With no hidden or late payment fees, it's easy to budget for your trip and snap up travel deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.