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, (162)
"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, (4)
"We thoroughly enjoyed this cottage and location for weekend during lacrosse tournaments. Much better than staying in hotel and perfect on the water to enjoy some family time! Thanks Angela! "
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

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

10.0 out of 10, Exceptional, (1)
"Good experience"
The price is NZ$1,125
includes taxes & fees
8 July - 9 July
Charming 2-bedroom cabin close to Fair Hill on horse farm

Saltwater Pool - Entire 4 BR Home + Yard is What You Need this Summer

Saltwater Pool - Entire 4 BR Home + Yard is What You Need this Summer

Cozy 2-bedroom apartment in Wilmington with AC , WiFi and Private Parking.

9.6 out of 10, Exceptional, (4)
"Nice place! Bedrooms were huge and we enjoyed our stay! "
Cozy 2-bedroom apartment in Wilmington with AC , WiFi and Private Parking.

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 NZ$504
includes taxes & fees
8 July - 9 July
Private townhouse near downtown and state park

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

Nature's Haven Tiny Home

10.0 out of 10, Exceptional, (2)
"Enjoyed"
The price is NZ$390
includes taxes & fees
7 July - 8 July
Nature's Haven Tiny Home

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

8.8 out of 10, Excellent, (5)
"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 NZ$346
includes taxes & fees
15 July - 16 July
Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.

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!

Cozy 2-bedroom townhome in charming Elkton

8.8 out of 10, Excellent, (5)
"We stayed for two nights and the beds were very comfortable. The house met our needs for the short time we were in town. I do wish somewhere it was disclosed that it backed up to a railroad track that is used day and night for commuter rail and we had a large freight train come by both nights at roughy 345am. "
Cozy 2-bedroom townhome in charming Elkton

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

10.0 out of 10, Exceptional, (54)
"The house is roomy and was clean and well stocked."
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows

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

8.4 out of 10, Very good, (13)
"Thanks Sean "
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..

Newark Rental Near University of Delaware!

3.0 star property
Newark Rental Near University of Delaware!

Historic Chesapeake City Stay

9.2 out of 10, Wonderful, (9)
"Always a nice get away…."
The price is NZ$464
includes taxes & fees
7 July - 8 July
Historic Chesapeake City Stay

New Construction townhome close to everything downtown w/transparent pricing

9.8 out of 10, Exceptional, (17)
"Beautiful home. Lisa was so lovely to specially set up a room for my 86 year old mother! We would not hesitate to stay again!!"
The price is NZ$399
includes taxes & fees
7 July - 8 July
New Construction townhome close to everything downtown w/transparent pricing

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!!!

Villa in Wilmington's Chateau Country

8.8 out of 10, Excellent, (6)
"Everything was as promised. We enjoyed the property. Luke did a great job walking us through the rental process."
Villa in Wilmington's Chateau Country

Cozy 2-bedroom in downtown Wilmington, perfect for work-related or leisure stay.

6.8 out of 10, (3)
"Host was very pushy and kicked us out on assumptions. House is in the ghetto."
Cozy 2-bedroom in downtown Wilmington, perfect for work-related or leisure stay.

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
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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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.