Port Penn Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Vacation Rentals in Port Penn

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (164)
"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, (6)
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

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

9.2 out of 10, Wonderful, (5)
The price is CA $592
CA $806 total
includes taxes & fees
Aug 3 - Aug 4
Charming 2-bedroom cabin close to Fair Hill on horse farm

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 CA $150
CA $253 total
includes taxes & fees
Aug 5 - Aug 6
Hello, welcome to our COMFY 2 BEDROOM apartment located in Wilmington Delaware.

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 CA $220
CA $419 total
includes taxes & fees
Jul 23 - Jul 24
Private townhouse near downtown and state park

Historic Chesapeake City Stay

9.0 out of 10, Wonderful, (11)
"Always a nice get away…."
The price is CA $148
CA $381 total
includes taxes & fees
Jul 28 - Jul 29
Historic Chesapeake City Stay

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

Ultimate Retreat @ Papermill Rd

9.0 out of 10, Wonderful, (6)
"Great weekend stay"
Ultimate Retreat @ Papermill Rd

Nature's Haven Tiny Home

10.0 out of 10, Exceptional, (2)
"Enjoyed"
The price is CA $259
CA $323 total
includes taxes & fees
Jul 24 - Jul 25
Nature's Haven Tiny Home

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

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!

Luxury 2-bedroom house with Water views, Chesapeake City

2.0 star property
10.0 out of 10, Exceptional, (2)
"This is a gorgeous property with a great water view of the canalThe house is beautifully decorated and comfortable, and we loved the upper deck. We had a few issues and Gwen addressed them quickly. The restaurants in town are great and in walking distance. There are interesting areas nearby to explore. "
Luxury 2-bedroom house with Water views, Chesapeake City

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

Two-story condo in luxury townhouse. Free parking.

9.6 out of 10, Exceptional, (15)
"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!"
The price is CA $295
CA $492 total
includes taxes & fees
Jul 28 - Jul 29
Two-story condo in luxury townhouse. Free parking.

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, (19)
"Everyone in our family ages 8, 10, 17, 18, 38, 64, and 71 thought the house and location were perfect and we had a great stay."
Chesapeake City Quiet Overlook

Beachfront Sunsets on the Water at Oakwood Beach

10.0 out of 10, Exceptional, (37)
"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 CA $665
CA $1,094 total
includes taxes & fees
Jul 28 - Jul 29
Entire two-unit four-story townhouse, for multi-family vacations; free parking

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.

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

8.6 out of 10, Excellent, (14)
"Thanks Sean "
Spacious Single Family Home Near Water, Recreational Areas/Parks, and Shopping..
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Port Penn Hotel Reviews

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 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.