Port Penn Holiday Rentals

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Our top choices for Port Penn holiday rentals

9.8 out of 10, Exceptional, (40)
"Absolutely love the accommodations. First impression when entering room was so fresh and clean."
United States
Beverly M.
The price is AU$170
includes taxes & fees
22 Dec - 23 Dec
Country Get Away 1 Bedroom Apartment
9.4 out of 10, Exceptional, (3)
"House clean ac work great on hot weekends. Great bike path near by and nice restaurants by and the river was great on bike . Not to far from Dover for race I would stay again "
United States
Wayne
The price is AU$508
includes taxes & fees
18 Dec - 19 Dec
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
2.0 star property
8.0 out of 10, Very good, (3)
"This unit is very much as depicted in photos on VRBO site. The neighborhood is interesting and feels safe, and the unit itself is very authentic to residential multi units built, I'm guessing, about 100 years ago. We recommend this place. "
United States
Thomas D.
The price is AU$549
includes taxes & fees
14 Dec - 15 Dec
The Gilpin Getaway | 2BR | Free Coffee | by RedAwning

Cabin in Chesapeake City

Historic Chesapeake City Stay
9.0 out of 10, Wonderful, (20)
"This place was very cute and clean, also convenient to Shaefers Marina. It was a perfect place for us to spend a weekend on the bay. "
United States
Benay N.
The price is AU$375
includes taxes & fees
15 Dec - 16 Dec
Historic Chesapeake City Stay

Apartment in Bear

Cozy loft above ink shop
9.6 out of 10, Exceptional, (5)
The price is AU$177
includes taxes & fees
14 Dec - 15 Dec
Cozy loft above ink shop
8.8 out of 10, Excellent, (13)
"Very quiet place with comfortable bed. Great overnight stay!"
United States
Rhonda Y.
The price is AU$263
includes taxes & fees
14 Dec - 15 Dec
Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.
9.8 out of 10, Exceptional, (8)
"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "
United States
Laurie S.
The price is AU$533
includes taxes & fees
14 Dec - 15 Dec
Amazing Modern house with a full kitchen and parking
9.8 out of 10, Exceptional, (22)
"Very nice and clean. We do work on Fire Apparatus in the area and this will be my go to spot when in the area."
United States
Peter F.
The price is AU$276
includes taxes & fees
17 Dec - 18 Dec
New Construction townhome close to everything downtown w/transparent pricing
10.0 out of 10, Exceptional, (3)
"Enjoyed our stay."
United States
Erik H.
The price is AU$410
includes taxes & fees
5 Jan - 6 Jan 2026
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
The price is AU$350
includes taxes & fees
4 Jan - 5 Jan 2026
Free Breakfast. Pool. 10 Min Drive to the University of Delaware!

Holiday Home in Smyrna

JVA LUXURY HOUSING
10.0 out of 10, Exceptional, (1)
"The house was clean and wonderful. I highly recommend!"
United States
Daryl C.
The price is AU$895
includes taxes & fees
20 Dec - 21 Dec
JVA LUXURY HOUSING
2.0 star property
The price is AU$164
includes taxes & fees
18 Dec - 19 Dec
Room #2 in Elkton, MD – Easy Access to I-95
6.0 out of 10, (1)
"I'll say up front that I should have looked closer at the listing. We were trying to be close to family. So, location sold us on it. Pros: This property is in a good location/quiet street. The unit itself was clean. The double bed was comfortable The communication/check-in/etc. were all ok. Cons: On-street parking is challenging. The property is in an old building and it shows. The unit has been painted, but it still felt very run-down. Common/Entry hallway smelled of tobacco ... "
United States
James S.
The price is AU$428
includes taxes & fees
14 Dec - 15 Dec
Trolley Teacup Charming Cozy Studio by RedAwning
10.0 out of 10, Exceptional, (1)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
The price is AU$516
includes taxes & fees
14 Dec - 15 Dec
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

Holiday Home in Wilmington

A Cool Place to Stay in Wilmington DE
The price is AU$235
includes taxes & fees
14 Dec - 15 Dec
A Cool Place to Stay in Wilmington DE
9.4 out of 10, Exceptional, (20)
"Very nice property, just right size for our needs. Great neighborhood. Kitchen very nice, check in easy."
United States
Lori W.
The price is AU$557
includes taxes & fees
30 Dec - 31 Dec
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE
8.0 out of 10, Very good, (10)
"Nice and quiet place to stay"
United States
Gary M.
The price is AU$431
includes taxes & fees
15 Dec - 16 Dec
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
9.6 out of 10, Exceptional, (16)
"This is a great place and super conveniently located. We loved all the amenities! Special shout out for the lovely towels! We would definitely stay here again!"
United States
Shelly S.
The price is AU$543
includes taxes & fees
14 Dec - 15 Dec
Two-story condo in luxury townhouse. Free parking.
2.0 star property
Cozy 1-bedroom apartment in tranquil Hockessin with AC
9.6 out of 10, Exceptional, (11)
"Good place to stay, well kept, spacious and updated. "
United States
Kevin L.
The price is AU$1,315
includes taxes & fees
13 Jan - 14 Jan 2026
Entire two-unit four-story townhouse, for multi-family vacations; free parking
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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Top Port Penn Hotel Reviews

Find out more about Port Penn

Everything you need to know about Port Penn holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Port Penn holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Port Penn holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Port Penn holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Port Penn. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Port Penn holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Port Penn holiday rentals we have selected for you start as low as AU$170 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Port Penn rentals

At Expedia, we put the best Port Penn holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Port Penn rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Port Penn holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Port Penn. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Port Penn?

Yes, there are holiday rentals close to the most popular sights in Port Penn, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Port Penn has to offer?

Private townhouse near downtown and state park: This holiday home rental outside of Port Penn has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

What can I see and do in Port Penn?

While exploring the area, visit family-friendly sights like Bowlerama, or get outside and enjoy nature at Chespeake & Delaware Branch Canal. Fort DuPont State Park and Fort Delaware State Park are a couple of places you'll find in the wider area.

What are holiday rentals like in Port Penn?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Port Penn. Holiday rentals feature amenities such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of privacy away from shared hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a great option for a small group gathering.