Port Penn Vacation Rentals

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Vacation Rentals in Port Penn

Chesapeake Bay House with Dock & Private Beach

Elkton
10.0 out of 10, Exceptional, (178)
"We loved this house and had the best time!!"
United States
Laura C.
Chesapeake Bay House with Dock & Private Beach

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

Wilmington
8.8 out of 10, Excellent, (13)
"Very quiet place with comfortable bed. Great overnight stay!"
United States
Rhonda Y.
$170 nightly
The price is $174
Dec 9 - Dec 10
Total with taxes and fees
Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.

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

Elkton
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

Two-story condo in luxury townhouse. Free parking.

Downtown Wilmington
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.
$350 nightly
The price is $360
Dec 9 - Dec 10
Total with taxes and fees
Two-story condo in luxury townhouse. Free parking.

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

Elkton
9.6 out of 10, Exceptional, (14)
"Excellent stay! "
United States
Edward S.
Charming 2-bedroom cabin close to Fair Hill on horse farm

Private townhouse near downtown and state park

Downtown Wilmington
9.4 out of 10, Exceptional, (11)
"Great little spot in a perfect location for us"
United States
j m.
$265 nightly
The price is $272
Dec 9 - Dec 10
Total with taxes and fees
Private townhouse near downtown and state park

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

Earleville
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.

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

Elkton
10.0 out of 10, Exceptional, (1)
"The house was clean and a nice place. The kitchen was nice. "
United States
Anthony C.
$322 nightly
The price is $341
Dec 9 - Dec 10
Total with taxes and fees
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

Tiny Home Tranquil Oasis

Bear
Tiny Home Tranquil Oasis

Historic Chesapeake City Stay

Chesapeake City
9.0 out of 10, Wonderful, (19)
"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.
$263 nightly
The price is $279
Dec 9 - Dec 10
Total with taxes and fees
Historic Chesapeake City Stay

Room #3 in Elkton, MD – Easy Access to I-95

2.0 star property
Elkton
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.
$117 nightly
The price is $123
Dec 18 - Dec 19
Total with taxes and fees
Room #3 in Elkton, MD – Easy Access to I-95

Beachfront Sunsets on the Water at Oakwood Beach

Salem
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

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

Chesapeake City
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

Country Get Away 1 Bedroom Apartment

Elkton
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.
$105 nightly
The price is $111
Dec 15 - Dec 16
Total with taxes and fees
Country Get Away 1 Bedroom Apartment

Unique 10 bedrooms for 20+Person

2.0 star property
Baynard Village
$1,826 nightly
The price is $1,890
Dec 9 - Dec 10
Total with taxes and fees
Unique 10 bedrooms for 20+Person

Nature's Haven Tiny Home

Bear
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

5BR Private House for long stays

2.0 star property
Brandywine Village
$1,019 nightly
The price is $1,052
Dec 9 - Dec 10
Total with taxes and fees
5BR Private House for long stays

Charming 3-bedroom house with AC and WiFi in lovely Wilmington

Hilltop
10.0 out of 10, Exceptional, (3)
"This property was very comfortable, the location was great quiet, clean and family friendly. I would definitely stay again."
United States
Ronnina M.
Charming 3-bedroom house with AC and WiFi in lovely Wilmington

Chesapeake Point | Waterfront w/ HOT TUB + Beach!

Elkton
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!

Chesapeake City Pool Retreat – Waterfront Stay in the Woods

Elkton
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
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 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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Port Penn in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $111 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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 Bay House with Dock & Private Beach: Visitors like this Port Penn vacation home rental. It is located on the beach and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like 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 DuPont State Park and Fort Delaware State Park 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.