Port Penn Vacations from $227

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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.
Hyatt Place Miami Airport-East

Hyatt Place Miami Airport-East

3 out of 5
Palmer Lake
Save 100% on your flight
Price was $448, price is now $227 per person
$227
per person
Mar 16 - Mar 19
found 2 days ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (2,247 reviews)
Room was nice, clean and beautiful view of the airport. A little noisy because of the airport but was nice. Never got to try the breakfast as we had an early flight. Easy check in process, will hold luggage so you don’t have to hold it till you get to check in.

Reviewed on Feb 3, 2026

Creekside Inn

Creekside Inn

2.5 out of 5
Price was $1,440, price is now $644 per person
$644
per person
Mar 15 - Mar 20
found 2 days ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1,004 reviews)
Room was clean, spacious with a wonderful canal view.

Reviewed on Jan 27, 2026

Broadmore Miami Beach

Broadmore Miami Beach

3.5 out of 5
North Beach
Price was $616, price is now $283 per person
$283
per person
Mar 16 - Mar 20
found 2 days ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
5.6/10 (389 reviews)
What stood out the most is it’s an original hotel from the 1940’s. I cherish that. Elevator was very slow but its 60 plus years old. Admire the authenticity of this hotel. Key cards for the room are my ONLY complaint. Should be keys not cards. Staff is absolutely amazing. Right on the beach! Book it. You won’t be disappointed unless you want 5 star 2026. Thank you for everything broadmore!!!

Reviewed on Jan 31, 2026

Los Angeles Deluxe Suites - 2 Bedrooms & 2 Bathrooms

Los Angeles Deluxe Suites - 2 Bedrooms & 2 Bathrooms

4.5 out of 5
Hollywood
Price was $2,714, price is now $1,272 per person
$1,272
per person
Apr 13 - Apr 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Los Angeles (LAX)
9.2/10 Wonderful! (80 reviews)
We loved our stay here! Having an apartment was home away from home. Quiet neighborhood, close to everything. Comfy beds are hard to find and i was very pleased. Host was quick to respond.

Reviewed on Jan 23, 2026

The Penguin Hotel

The Penguin Hotel

3.5 out of 5
South Beach
Save 100% on your flight
Price was $920, price is now $458 per person
$458
per person
Apr 25 - Apr 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (1,491 reviews)
Muy buena atención y buen servicio super recomendable gracias

Reviewed on Feb 5, 2026

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Discover the most popular places to visit in Port Penn

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

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

Port Penn Hotel Deals

Sheraton Suites Wilmington Downtown

Sheraton Suites Wilmington Downtown

3.5 out of 5
422 Delaware Ave Wilmington DE
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $140 total per night from Feb 12 to Feb 13
$140 total
Feb 12 - Feb 13
Total with taxes and fees
8.2/10 Very Good! (1,000 reviews)
Always the best place with early check in. Clean and cozy with super awesome customer service.

Reviewed on Jan 20, 2026

Sheraton Suites Wilmington Downtown
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
$102 nightly
The price is $113 total per night from Feb 22 to Feb 23
$113 total
Feb 22 - Feb 23
Total with taxes and fees
8.2/10 Very Good! (1,009 reviews)
Great room and excellent environment!

Reviewed on Feb 2, 2026

Embassy Suites by Hilton Newark Wilmington South
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
$94 nightly
The price is $105 total per night from Feb 6 to Feb 7
$105 total
Feb 6 - Feb 7
Total with taxes and fees
7.6/10 Good! (1,254 reviews)
Perfect

Reviewed on Jan 30, 2026

Sonesta Select Newark Christiana Mall
See all 471 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

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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 $227 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.