Holiday Rentals in Port Penn

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Our top choices for Port Penn holiday rentals

Holiday Home in Downtown Wilmington

Private townhouse near downtown and state park
9.4 out of 10, Exceptional, (12)
"Great little spot in a perfect location for us"
United States
j m.
The price is €248
includes taxes & fees
17 Dec - 18 Dec
Private townhouse near downtown and state park
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 €298
includes taxes & fees
17 Dec - 18 Dec
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
10.0 out of 10, Exceptional, (180)
"We loved this house and had the best time!!"
United States
Laura C.
Chesapeake Bay House with Dock & Private Beach
8.8 out of 10, Excellent, (14)
"Very quiet place with comfortable bed. Great overnight stay!"
United States
Rhonda Y.
The price is €152
includes taxes & fees
17 Dec - 18 Dec
Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.
9.8 out of 10, Exceptional, (14)
"It was a lovely home and we very much enjoyed our stay. Clean, comfortable beds and great location. "
United States
Deborah M.
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
9.8 out of 10, Exceptional, (20)
"Had a good time, grandkids never came out of the pool"
United States
Michael D.
Stunning waterfront villa with indoor pool and kids swing set and play area.

Mobile Home in Bear

Tiny Home Tranquil Oasis
Tiny Home Tranquil Oasis
10.0 out of 10, Exceptional, (72)
"Great house close to canal and downtown Chesapeake City!"
United States
Michael M.
Fall Season in Chesapeake City, MD 'Old Lock View' @ C&D Canal

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 €251
includes taxes & fees
15 Jan - 16 Jan 2026
Historic Chesapeake City Stay
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 €99
includes taxes & fees
29 Dec - 30 Dec
Country Get Away 1 Bedroom Apartment
2.0 star property
5.0 out of 10, (2)
"For our first time trying shared spaces. Over all, the pros; The room was in a nice home in a very quiet and decent housing development. The home was neat decorated in a minimalist style. The bed was very comfortable, pillows and bedding, and hot shower and bath water with soap provided. The kitchen/dining area was just right for cooking and dining and cleaning up had the minimal supplies needed. The sitting areas were very relaxing to watch T.V. and or just lounge. Common bathroom off living...
United States
Nicomedes M R.
The price is €109
includes taxes & fees
13 Jan - 14 Jan 2026
Room #3 in Elkton, MD – Easy Access to I-95
10.0 out of 10, Exceptional, (44)
"Excellent property and outstanding hosts. Peaceful, relaxing, and a wonderful spot to finish out the summer. The provided amenities exceeded expectations. The house has everything needed for a home away from home vacation rental. "
United States
Craig F.
Beachfront Sunsets on the Water at Oakwood Beach
10.0 out of 10, Exceptional, (1)
"From start to finish this trip was AMAZING! Mr. Ray was accommodating and responded in a timely manner. The property was very well kept and had everything that was needed. Another thing that really stood out what that everything was labeled. We will definitely be booking another stay at The Pointe."
United States
Khadijah F.
The Pointe is on the Elk River on the Upper Chesapeake Bay
9.6 out of 10, Exceptional, (14)
"Excellent stay! "
United States
Edward S.
Charming 2-bedroom cabin close to Fair Hill on horse farm
9.8 out of 10, Exceptional, (19)
"We all got together from various parts of the country to enjoy ourselves at this lovely place."
United States
MARK M.
Chesapeake Point | Waterfront w/ HOT TUB + Beach!
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 €159
includes taxes & fees
17 Dec - 18 Dec
New Construction townhome close to everything downtown w/transparent pricing

Mobile Home in Bear

Nature's Haven Tiny Home
10.0 out of 10, Exceptional, (4)
"Nature’s Haven Tiny Home worked great for us. Karin was a great communicator and we really enjoyed ourselves. "
United States
James S.
Nature's Haven Tiny Home
8.8 out of 10, Excellent, (15)
"Lovely place. We really enjoyed our stay"
United States
Renae R.
Chesapeake City Pool Retreat – Waterfront Stay in the Woods
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 €310
includes taxes & fees
17 Dec - 18 Dec
Two-story condo in luxury townhouse. Free parking.

Holiday Home in Baynard Village

Unique 10 bedrooms for 20+Person
2.0 star property
The price is €1,611
includes taxes & fees
17 Dec - 18 Dec
Unique 10 bedrooms for 20+Person
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, 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 €99 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?

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.