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Port Penn Vacation Rentals

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Our top choices for Port Penn vacation rentals

1. Elegant Family Stay • Quiet Neighborhood • Comfort

Elegant Family Stay • Quiet Neighborhood • Comfort
New Castle
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful well kept property with lots of room to relax."
United States
Daniel J.
The price is CA $432
CA $565 total
includes taxes & fees
Nov 29 - Nov 30
Elegant Family Stay • Quiet Neighborhood • Comfort

2. Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail

Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail
Bear
9.8 out of 10, Exceptional, (7 reviews)
"Great stay. Awesome owner. Nice restaurant right up the ramp. Would def recommend and do again if in the area!!!"
United States
Justin M.
The price is CA $350
CA $396 total
includes taxes & fees
Nov 7 - Nov 8
Come stay on our 40 Viking yacht - two bedrooms with restaurant and biking trail

3. Nature's Haven Tiny Home

Nature's Haven Tiny Home
Bear
10.0 out of 10, Exceptional, (4 reviews)
"Great place to relax after a while on the go. Karin was very friendly and informative about places to see in the area. Everything was great "
United States
Maxwell
The price is CA $264
CA $311 total
includes taxes & fees
Nov 5 - Nov 6
Nature's Haven Tiny Home

4. Tiny Home Tranquil Oasis

Tiny Home Tranquil Oasis
Bear
10.0 out of 10, Exceptional, (2 reviews)
"This was a stop over on our way to the beach- it was a convenient comfy space for our family."
United States
Erin C.
The price is CA $264
CA $354 total
includes taxes & fees
Nov 5 - Nov 6
Tiny Home Tranquil Oasis

5. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.2 out of 10, Wonderful, (31 reviews)
"Cute place. Clean, comfortable, and convenient to the soccer complex. I wasn’t familiar with Chesapeake City but we had a great time at the waterfront restaurants."
United States
John P.
The price is CA $189
CA $419 total
includes taxes & fees
Nov 5 - Nov 6
Historic Chesapeake City Stay

6. Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..

Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
New Castle
8.4 out of 10, Very good, (24 reviews)
"I’ve stayed in much better locations."
United States
Grant H.
The price is CA $250
CA $512 total
includes taxes & fees
Nov 8 - Nov 9
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..

7. Country Get Away Studio Apartment

Country Get Away Studio Apartment
Elkton
9.8 out of 10, Exceptional, (52 reviews)
"Beautiful quiet country getaway. Setting, nature was great."
United States
JAMES V.
The price is CA $98
CA $144 total
includes taxes & fees
Nov 10 - Nov 11
Country Get Away Studio Apartment

8. Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure

Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure
Chesapeake City
9.6 out of 10, Exceptional, (7 reviews)
"Everything was as advertised. Property is not new, but everything was clean and well cared for. Evenings on the water were peaceful and relaxing. We enjoyed our stay and definitely intend to return."
United States
John
The price is CA $201
CA $393 total
includes taxes & fees
Nov 5 - Nov 6
Charming Water-Front Cottage Perfectly Suited for Rest, Relaxation, and Leisure

9. Charming 3-bedroom, two-living room Victorian home in Historic New Castle

Charming 3-bedroom, two-living room Victorian home in Historic New Castle
Historical Old New Castle
The price is CA $403
CA $735 total
includes taxes & fees
Nov 5 - Nov 6
Charming 3-bedroom, two-living room Victorian home in Historic New Castle

10. The Penthouse Flat - 3bd/1ba, Laundry, Pet-Friendly

The Penthouse Flat - 3bd/1ba, Laundry, Pet-Friendly
Pennsville Township
The price is CA $385
CA $966 total
includes taxes & fees
Nov 13 - Nov 14
The Penthouse Flat - 3bd/1ba, Laundry, Pet-Friendly

11. Free Breakfast. Pool. 10 Min Drive to the University of Delaware!

Free Breakfast. Pool. 10 Min Drive to the University of Delaware!
Newark
10.0 out of 10, Exceptional, (1 review)
"Clean rooms close to all things we needed breakfast was good and plentiful wish the afternoon buffet was available would use this place again"
United States
Susan H.
The price is CA $341
CA $407 total
includes taxes & fees
Nov 22 - Nov 23
Free Breakfast. Pool. 10 Min Drive to the University of Delaware!

12. Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware

Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware
Newark
9.8 out of 10, Exceptional, (8 reviews)
"Enjoyed our stay."
United States
Erik H.
The price is CA $229
CA $507 total
includes taxes & fees
Dec 1 - Dec 2
Private Home + 3 Bed/1.5 Bath + 2MI - University of Delaware

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

Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes
Elkton
9.8 out of 10, Exceptional, (6 reviews)
"Wonderful spot for five ladies to enjoy an evening away close to Chesapeake City"
United States
Rebecca G.
The price is CA $253
CA $508 total
includes taxes & fees
Nov 9 - Nov 10
Family-Friendly 4BR Home in Elkton - AC, High-Speed WiFi & Relaxing Vibes

14. Entire place with private parking

Entire place with private parking
Hilltop
8.0 out of 10, Very good, (11 reviews)
"great place very clean. Will stay again loved private parking "
United States
kennya J.
The price is CA $146
CA $218 total
includes taxes & fees
Nov 5 - Nov 6
Entire place with private parking

15. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
8.0 out of 10, Very good, (1 review)
The price is CA $782
CA $828 total
includes taxes & fees
Nov 11 - Nov 12
Bohemia Manor Farm

16. Perfect for Groups! | Pool + Gym + Free Breakfast

Perfect for Groups! | Pool + Gym + Free Breakfast
Newark
The price is CA $357
CA $427 total
includes taxes & fees
Nov 22 - Nov 23
Perfect for Groups! | Pool + Gym + Free Breakfast

17. Delightful 4-bedroom house in Carneys Point Township, near Wilmington & Philly!

Delightful 4-bedroom house in Carneys Point Township, near Wilmington & Philly!
Carneys Point Township
The price is CA $376
CA $915 total
includes taxes & fees
Nov 9 - Nov 10
Delightful 4-bedroom house in Carneys Point Township, near Wilmington & Philly!

18. Harmony Family Estate A Beautiful 5-bedroom house in Wilmington for your group

Harmony Family Estate A Beautiful 5-bedroom house in Wilmington for your group
Wilmington
9.4 out of 10, Exceptional, (11 reviews)
"Comfy cozy… home away from home. Location was perfectly centered for the activities we did and the restaurants we chose. Beds and sheets were great and plenty of hot water. We had a nice relaxing stay."
United States
carla k.
The price is CA $264
CA $526 total
includes taxes & fees
Nov 12 - Nov 13
Harmony Family Estate A Beautiful 5-bedroom house in Wilmington for your group

19. Modern 1BR in Downtown Wilmington Near Riverwalk & Restaurants

Modern 1BR in Downtown Wilmington Near Riverwalk & Restaurants
Downtown Wilmington
9.0 out of 10, Wonderful, (2 reviews)
"There was leak from upstairs the day before but they had cleaned it all up except for a really sticky floor. Traffic was load but a great location. Tricky getting the garage pass with no parking in front. I recommend indications for pulling around the corner and running in for the parking pass."
United States
Jon N.
The price is CA $132
CA $211 total
includes taxes & fees
Nov 8 - Nov 9
Modern 1BR in Downtown Wilmington Near Riverwalk & Restaurants

20. Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!

Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
Newark
The price is CA $226
CA $269 total
includes taxes & fees
Nov 30 - Dec 1
Free Breakfast. Outdoor Pool. 10 Min from University of Delaware!
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Port Penn. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Sunset River Cottage: Visitors like this Port Penn vacation home rental. It is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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 Dragon Run Park. 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.