Port Penn Holiday Rentals

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Holiday Rentals in Port Penn

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

9.6 out of 10, Exceptional, (7)
"Good experience"
Charming 2-bedroom cabin close to Fair Hill on horse farm

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

8.4 out of 10, Very good, (8)
"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 NZ$321
includes taxes & fees
28 Sept - 29 Sept
Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.

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

9.8 out of 10, Exceptional, (19)
"Clean and comfortable stay in quiet neighborhood! Communication with the host was pleasant and prompt."
The price is NZ$578
includes taxes & fees
28 Sept - 29 Sept
Serene Townhome minutes away from Christiana Mall, DE Race Park and Univ. of DE

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (172)
"Property was in good shape and had plenty of space. Our family loved the beach and the shallow water for the children to play in. Even though we didn’t have perfect weather, we had a wonderful trip."
Chesapeake Bay House with Dock & Private Beach

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 NZ$214
includes taxes & fees
5 Oct - 6 Oct
Charming 2-bedroom house with WiFi, AC in marvelous Wilmington

Historic Chesapeake City Stay

9.0 out of 10, Wonderful, (15)
"Always a nice get away…."
The price is NZ$479
includes taxes & fees
30 Sept - 1 Oct
Historic Chesapeake City Stay

Tiny Home Tranquil Oasis

The price is NZ$415
includes taxes & fees
27 Sept - 28 Sept
Tiny Home Tranquil Oasis

Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6

10.0 out of 10, Exceptional, (1)
"Property is beautiful, host answered our questions in a timely manner. Would stay again "
Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6

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

New Construction townhome close to everything downtown w/transparent pricing

9.8 out of 10, Exceptional, (17)
"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."
The price is NZ$384
includes taxes & fees
5 Oct - 6 Oct
New Construction townhome close to everything downtown w/transparent pricing

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

9.8 out of 10, Exceptional, (6)
"We rented Hook, Wine & Sinker for our family to stay in during the weekend of our son's wedding in Chesapeake City, MD. The home is absolutely beautiful, very clean, spacious, and one of the best rentals that I've stayed in with VRBO. "
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!

Stunning waterfront villa with indoor pool and kids swing set and play area.

9.8 out of 10, Exceptional, (18)
"Wonderful location, lots to do, close to Chesapeake City, excellent host"
Stunning waterfront villa with indoor pool and kids swing set and play area.

Charming apartment in serene Wilmington with AC

8.0 out of 10, Very good, (1)
"The host and actual apartment are great - clean, nice bathroom, the host was so friendly and left amazing treats, including a surprise for breakfast. The neighborhood was not great, and unfortunately was the only bad part about this stay. Otherwise I'd give 5 stars and would definitely stay with this host again."
The price is NZ$214
includes taxes & fees
30 Sept - 1 Oct
Charming apartment in serene Wilmington with AC

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

10.0 out of 10, Exceptional, (9)
"Great, cozy, quiet little spot! Perfect for 4 adults and a baby. My 1.5 year old loved exploring the deck with an amazing water view, and gained lots of confidence navigating the little steps throughout the house and worked on her balance. Kitchen was well appointed and suited our needs. Would stay here again!"
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

Nature's Haven Tiny Home

10.0 out of 10, Exceptional, (3)
"Enjoyed"
The price is NZ$400
includes taxes & fees
6 Oct - 7 Oct
Nature's Haven Tiny Home

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

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

Gilpin Grand - Renovated Space In Trolley Square 1 Bedroom Apts by RedAwning

3.0 star property
The price is NZ$555
includes taxes & fees
20 Oct - 21 Oct
Gilpin Grand - Renovated Space In Trolley Square 1 Bedroom Apts by RedAwning

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

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

Cozy loft above ink shop

10.0 out of 10, Exceptional, (1)
"Cozy little place to stay that was fully stocked for a fair price compared to others in the area. Plenty of parking and quiet even with the tattoo shop below. The only thing that I would like to have had is a light on the front porch but I used my flashlight on my phone so it wasn’t too bad. I would definitely stay again."
The price is NZ$168
includes taxes & fees
5 Oct - 6 Oct
Cozy loft above ink shop
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, 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 NZ$168 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. Fort Delaware State Park and Historic Houses of Odessa 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.