Port Penn Vacations from $307

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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.
The Cole

The Cole

3.5 out of 5
Little Tuscany
Price was $658, price is now $307 per person
$307
per person
Nov 9 - Nov 13
just found
Roundtrip flight included
Dallas (DFW) to Los Angeles (LAX)
8.4/10 Very Good! (293 reviews)
My third time always enjoy

Reviewed on Sep 5, 2025

Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was $1,632, price is now $741 per person
$741
per person
Dec 4 - Dec 8
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
Great staff. Nice rooms close to beach

Reviewed on Sep 2, 2025

Henrosa Hotel

Henrosa Hotel

3.5 out of 5
South Beach
Price was $1,480, price is now $676 per person
$676
per person
Dec 4 - Dec 8
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Miami (MIA)
8.4/10 Very Good! (818 reviews)
Beach staff was rude.

Reviewed on Sep 8, 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 $1,103, price is now $513 per person
$513
per person
Nov 13 - Nov 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Los Angeles (LAX)
9.2/10 Wonderful! (74 reviews)
Beds were good altough the bed covers were stained everything else was good.

Reviewed on Jul 31, 2025

El Noa Noa

El Noa Noa

2 out of 5
Warm Sands
Price was $732, price is now $345 per person
$345
per person
Nov 9 - Nov 13
just found
Roundtrip flight included
Dallas (DFW) to Los Angeles (LAX)
9.4/10 Exceptional! (50 reviews)
Loved staying here! I wish I could book all the time but they require a two night minimum. (only downside) other than that its our favorite place to stay but since I have kids I can't do more than one night stays. The bathroom is a beautiful open concept. Jacuzzi and private patio are literally what sold me. Rooms are clean and huge tv & plenty of amenities to choose from.

Reviewed on Aug 21, 2025

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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
$98 nightly
The price is $108 total per night from Sep 21 to Sep 22
$108 total
Sep 21 - Sep 22
Total with taxes and fees
DoubleTree by Hilton Downtown Wilmington - Legal District
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
$91 nightly
The price is $101 total per night from Sep 25 to Sep 26
$101 total
Sep 25 - Sep 26
Total with taxes and fees
Sonesta Select Newark Christiana Mall
Embassy Suites by Hilton Newark Wilmington South

Embassy Suites by Hilton Newark Wilmington South

3.5 out of 5
654 S College Ave, Newark, DE
Fully refundableReserve now, pay when you stay
$115 nightly
The price is $127 total per night from Sep 21 to Sep 22
$127 total
Sep 21 - Sep 22
Total with taxes and fees
Embassy Suites by Hilton Newark Wilmington South
See all 429 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.

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Frequently asked questions

How much does a Port Penn vacation package cost?
You can snap up a vacation package to this top destination from $307 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.