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Top Holiday Rentals in Port Penn

Our top choices for Port Penn holiday rentals

Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.

8.6 out of 10, Excellent, (7)
"Was in Wilmington to work a trade show at the Chase Center on the Riverfront. Everything was as described and the communications with the host were great. Only about a 12 minute drive to the venue and lots of restaurants within a 10 minute drive. It’s nothing fancy but for about the same price as a budget hotel room you get a kitchen, two comfy bedrooms and a living room. "
The price is £143
includes taxes & fees
27 Aug - 28 Aug
Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (170)
"Easy check in process. House very clean. Going location. "
Chesapeake Bay House with Dock & Private Beach

Historic Chesapeake City Stay

9.0 out of 10, Wonderful, (13)
"Always a nice get away…."
The price is £212
includes taxes & fees
28 Aug - 29 Aug
Historic Chesapeake City Stay

Charming 2-bedroom cabin close to Fair Hill on horse farm

9.2 out of 10, Wonderful, (5)
The price is £239
includes taxes & fees
2 Sept - 3 Sept
Charming 2-bedroom cabin close to Fair Hill on horse farm

Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

10.0 out of 10, Exceptional, (7)
"Can’t say enough about how nice this place is. We had quick friendly responses from owners. Very clean and the water front view was excellent. Highly recommended "
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

Chesapeake Point | Waterfront w/ HOT TUB + Beach!

9.8 out of 10, Exceptional, (17)
"Enjoyed our stay. Location is beautiful and peaceful! Great place for a large group."
Chesapeake Point | Waterfront w/ HOT TUB + Beach!

Tiny Home Tranquil Oasis

The price is £184
includes taxes & fees
27 Aug - 28 Aug
Tiny Home Tranquil Oasis

Private townhouse near downtown and state park

10.0 out of 10, Exceptional, (9)
"The house is clean and comfortable with many amenities and within walking distance of parks and restaurants and museums. The host was very easy to connect with."
The price is £233
includes taxes & fees
27 Aug - 28 Aug
Private townhouse near downtown and state park

Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!

9.8 out of 10, Exceptional, (6)
"Exactly as advertised and Brad was very helpful/responsive!"
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!

3 Mi to Dtwn: Home w/ Yard in Newark

9.2 out of 10, Wonderful, (9)
"We loved staying here, location is great!"
3 Mi to Dtwn: Home w/ Yard in Newark

Charming 2-bedroom house with WiFi, AC in marvelous Wilmington

2.0 out of 10, (1)
"Never heard from host. Expedia had to cancel reservation."
The price is £112
includes taxes & fees
16 Sept - 17 Sept
Charming 2-bedroom house with WiFi, AC in marvelous Wilmington

Elegant Retreat With Pool, Screened Porch Just Steps From Shops, Dining & Fun!

Elegant Retreat With Pool, Screened Porch Just Steps From Shops, Dining & Fun!

Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

9.8 out of 10, Exceptional, (19)
"We rented this townhouse for a month for my son's surgical residency rotation at Cristiana Care. It was a perfect location and easy to get to and from the hospital. Owner was very responsive with any questions / concerns which we appreciated. Very quiet and close to grocery stores. Even had a Trader Joe's close by!"
The price is £248
includes taxes & fees
3 Sept - 4 Sept
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

Country Get Away 1 Bedroom Apartment

9.8 out of 10, Exceptional, (37)
"We enjoyed our stay. The apartment is spotless and has everything you need. The property is beautiful with trails and a cabin in the woods you can visit. "
The price is £86
includes taxes & fees
3 Sept - 4 Sept
Country Get Away 1 Bedroom Apartment

Chesapeake City Pool Retreat – Waterfront Stay in the Woods

9.2 out of 10, Wonderful, (12)
"Great location right on the water. Great for fishing or just sitting and relaxing. The house is in a quiet secluded area but only 10 minutes from Chesapeake Bay. Pool was an awesome extra. My son enjoyed it. The home was clean and plenty of space. "
Chesapeake City Pool Retreat – Waterfront Stay in the Woods

Nature's Haven Tiny Home

10.0 out of 10, Exceptional, (3)
"Enjoyed"
The price is £178
includes taxes & fees
27 Aug - 28 Aug
Nature's Haven Tiny Home

Chesapeake City Quiet Overlook

10.0 out of 10, Exceptional, (21)
"We had a wonderful stay in Chesapeake City! The property was very clean, well stocked, and perfect for our family. The kitchen is gorgeous with a beautiful view of the water, and everything is labeled so items are easy to find and put away. Just a short walk to dinner at Schaefer’s Canal House and the trail. Highly recommend!"
Chesapeake City Quiet Overlook

Luxurious and spacious townhome with all necessary amenities awaits your stay.

9.4 out of 10, Exceptional, (9)
Luxurious and spacious townhome with all necessary amenities awaits your stay.

Waterfront House on the Upper Chesapeake Bay

9.6 out of 10, Exceptional, (7)
"My boyfriend and i had a great 2 days! So peaceful bing on the water. Cottage was equipped with everything you would need!"
Waterfront House on the Upper Chesapeake Bay

Fair Hill Cabin-10 mins to Newark/UD

2.0 star property
9.8 out of 10, Exceptional, (8)
"Nice rural setting, close to trails, herd of about 10 deer seen a few times"
Fair Hill Cabin-10 mins to Newark/UD
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

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, apart-hotels, 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 favorite 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 depends 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 £86 per night. Entering your travel dates in the search wizard you might find 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?

Chesapeake Bay House with Dock & Private Beach: This holiday home rental outside of Port Penn is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What can I see and do in Port Penn?

While exploring the area, visit family-friendly sights like Frightland, or get outside and enjoy nature at Chespeake & Delaware Branch Canal. Battery 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.