Port Penn Vacation Rentals

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Vacation Rentals in Port Penn

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

9.2 out of 10, Wonderful, (5)
"Good experience"
The price is CA $277
CA $435 total
includes taxes & fees
Sep 9 - Sep 10
Charming 2-bedroom cabin close to Fair Hill on horse farm

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 CA $152
CA $260 total
includes taxes & fees
Sep 9 - Sep 10
Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.

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 CA $177
CA $213 total
includes taxes & fees
Sep 9 - Sep 10
Charming 2-bedroom house with WiFi, AC in marvelous Wilmington

Historic Chesapeake City Stay

9.0 out of 10, Wonderful, (14)
"Always a nice get away…."
The price is CA $149
CA $386 total
includes taxes & fees
Sep 9 - Sep 10
Historic Chesapeake City Stay

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

10.0 out of 10, Exceptional, (1)
"The property is exactly as you see in the pictures/description. We were 4 adults, 4 kids (9 months to 13 years). Plenty of room for all of us. Hosts were quick to respond to any messages sent.Had a great 3 days here."
Elegant Retreat With Pool, Screened Porch Just Steps From Shops, Dining & Fun!

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

Chesapeake Point | Waterfront w/ HOT TUB + Beach!

9.8 out of 10, Exceptional, (18)
"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 CA $261
CA $334 total
includes taxes & fees
Sep 9 - Sep 10
Tiny Home Tranquil Oasis

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

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

10.0 out of 10, Exceptional, (9)
"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

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

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (172)
"Easy check in process. House very clean. Going location. "
Chesapeake Bay House with Dock & Private Beach

Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

10.0 out of 10, Exceptional, (1)
"The house was clean and a nice place. The kitchen was nice. "
The price is CA $220
CA $516 total
includes taxes & fees
Sep 15 - Sep 16
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

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 CA $142
CA $211 total
includes taxes & fees
Sep 15 - Sep 16
Charming apartment in serene Wilmington with AC

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.

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 CA $261
CA $327 total
includes taxes & fees
Sep 9 - Sep 10
Nature's Haven Tiny Home

Summer Season in Chesapeake City, MD 'Old Lock View' @ C&D Canal

10.0 out of 10, Exceptional, (70)
"Nice home great lication"
Summer Season in Chesapeake City, MD 'Old Lock View' @ C&D Canal

Cozy loft above ink shop

The price is CA $103
CA $135 total
includes taxes & fees
Sep 9 - Sep 10
Cozy loft above ink shop

Spacious modern 4-bedroom townhome in Wilmington, up to 10 people

6.0 out of 10, (2)
"My wife and I enjoyed our stay. The property is clean the host is great and responsive. The amenities are modern and the neighborhood is quiet and close to the highway. "
Spacious modern 4-bedroom townhome in Wilmington, up to 10 people
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 vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Port Penn vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Port Penn vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Port Penn vacation rentals we have selected for you start as low as CA $103 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 vacation 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 vacation.

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 vacation rental in Port Penn?

Yes, we give you a choice of vacation rentals close to top sights in Port Penn, or you can select a secluded option if you want a relaxing place to stay.

What are some of the best vacation home rentals in Port Penn?

Chesapeake Point | Waterfront w/ HOT TUB + Beach!: Visitors like this Port Penn vacation home rental. It is located on a river and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with an arcade game room and a hot tub.

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 larger area.

What are vacation rentals like in Port Penn?

Vacation rentals are private accommodations you can stay in for a couple days or more in Port Penn. Vacation rentals feature extras such as WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great choice for a family trip.