Port Penn Holiday Rentals

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Holiday Rentals in Port Penn

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (166)
"Great place for a long weekend. Easy travel to surrounding areas to explore."
Chesapeake Bay House with Dock & Private Beach

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

10.0 out of 10, Exceptional, (7)
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

Historic Chesapeake City Stay

9.0 out of 10, Wonderful, (11)
"Always a nice get away…."
The price is AU$433
includes taxes & fees
8 Aug - 9 Aug
Historic Chesapeake City Stay

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

9.2 out of 10, Wonderful, (5)
The price is AU$521
includes taxes & fees
25 Aug - 26 Aug
Charming 2-bedroom cabin close to Fair Hill on horse farm

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

9.8 out of 10, Exceptional, (6)
"Exactly as advertised and Brad was very helpful/responsive!"
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!

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

Private townhouse near downtown and state park

10.0 out of 10, Exceptional, (9)
"The house is clean and comfortable with many amenities and within walking distance of parks and restaurants and museums. The host was very easy to connect with."
The price is AU$477
includes taxes & fees
11 Aug - 12 Aug
Private townhouse near downtown and state park

Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows

10.0 out of 10, Exceptional, (55)
"The house is roomy and was clean and well stocked."
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows

Charming 3-bedroom lake house with a seasonal private pool and seasonal hot tub!

10.0 out of 10, Exceptional, (3)
"Exceptional rental. So many spots to gather with friends. Pool was clean and refreshing. The landscape was gorgeous. The lake was tranquil. The kitchen was well stocked with everything we needed. Seven women wanting a peaceful retreat. Your home exceeded our expectations. Thank you for having us!"
Charming 3-bedroom lake house with a seasonal private pool and seasonal hot tub!

Chesapeake City Pool Retreat – Waterfront Stay in the Woods

9.2 out of 10, Wonderful, (11)
"Great communication, easy to access, accommodations true to listing. Spacious, renovated living space. Great outdoor pool."
Chesapeake City Pool Retreat – Waterfront Stay in the Woods

Nature's Haven Tiny Home

10.0 out of 10, Exceptional, (2)
"Enjoyed"
The price is AU$366
includes taxes & fees
10 Aug - 11 Aug
Nature's Haven Tiny Home

Charming 3-bedroom house in wonderful Pennsville Township with AC, WiFi

The price is AU$490
includes taxes & fees
8 Aug - 9 Aug
Charming 3-bedroom house in wonderful Pennsville Township with AC, WiFi

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

8.4 out of 10, Very good, (6)
"Nice and quiet place to stay"
The price is AU$475
includes taxes & fees
25 Aug - 26 Aug
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

Hidden Gem! - Downtown

6.0 out of 10, (4)
"This is my second time staying, the host always make me feel comfortable. This will be my go to everytime I visit this area."
Hidden Gem! - Downtown

Chesapeake City Quiet Overlook

10.0 out of 10, Exceptional, (20)
"We attended a wedding across the canal from this house at the Chesapeake Inn. It was very cool to see these really large ships go by as we sat on the deck. Very nice accommodations here! Jane was a great host!"
Chesapeake City Quiet Overlook

Cozy 1-bedroom apartment in nice New Castle with WiFi, AC

2.0 star property
10.0 out of 10, Exceptional, (2)
"Tucked away but close to everything that is Historic New Castle. A perfect little stop if you are touring this part of our country. Food, shops, historic buildings all within a few blocks. Protestant and Catholic Churches just a few blocks walk if you are staying over Sunday. Try The Mercury Cafe & Teahouse. Cozy and great food/coffee/tea. Check out Jessop’s Tavern for food and a huge selection of beers."
Cozy 1-bedroom apartment in nice New Castle with WiFi, AC

The Loft on West

10.0 out of 10, Exceptional, (4)
"My mother and I enjoyed our stay at the charming Woodstown rental. Spacious kitchen and super comfy living room couch. Rustic charm with modern touches. Great safety features, too - motion sensor lights on steps and in the kitchen, with high quality baby/pet gates. Being a pet friendly rental is also a plus. Located within walking distance to great eateries. "
The price is AU$937
includes taxes & fees
7 Sept - 8 Sept
The Loft on West

Beachfront Sunsets on the Water at Oakwood Beach

10.0 out of 10, Exceptional, (38)
"We travel in the winter in an RV. We had a friend and nephew who we wanted to spend time with and this house was perfect. The weather was very windy but having the beach right out the door was.perfect motovation to "
Beachfront Sunsets on the Water at Oakwood Beach

Entire two-unit four-story townhouse, for multi-family vacations; free parking

9.6 out of 10, Exceptional, (9)
"An excellent stay once again. Our host was friendly and the house was amazing per usual. Thank you!"
The price is AU$1,244
includes taxes & fees
11 Aug - 12 Aug
Entire two-unit four-story townhouse, for multi-family vacations; free parking

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
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

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.