Vacation rentals in Port Penn

The Pearl: A hip & cozy canal-side apartment

The Pearl is located in the heart of historic Chesapeake City; just steps from all the boutiques, restaurants & nightlife with a lovely view of the C&D Canal. It's cozy, but functional with 2 workspaces, 2 bedrooms & all the amenities you'd want in your home away! We provide a Nespresso machine & excellent coffee, snacks, sparkling water, full kitchen,etc. It's got a 70s vibe, an eclectic combo of euro/scan/boho hip! It's not your usual Victorian spot. Come stay with us, you won't regret it!

Elegant Spacious Family Gem • 20 Min to Wilmington

Step into the spacious and elegant 3BR 2.5BA family getaway in the tranquil and friendly New Castle neighborhood. It promises a relaxing retreat with quick access to I‑95 and Route 1, with a short drive from the tax-free Christiana Mall, restaurants, shops, and exciting attractions. The vintage ambiance paired with modern comforts and a rich amenity list will leave you in awe. ✔ 3 Comfortable Bedrooms ✔ 3 Lounge Areas ✔ Full Kitchen ✔ Backyard ✔ Smart TV ✔ Wi-Fi ✔ Parking Learn more below!

Private Guest Suite

Our suite features a 3-speed ceiling fan with dimmable overhead lighting, a kitchenette, a bidet toilet, an office nook, and more. While this space is most comfortable for 2 people, up to 2 additional people may be added to your reservation for a fee and we will provide an air mattress. Please note: our home shares a small mud room-style entrance with the guest suite, however the suite has a lock and is private with its own bedroom, bathroom, and kitchenette. We look forward to hosting you!

Private Suburban Studio Apt/Free P/Quite Location

*Peaceful location/Central A/C to beat the heat.Quiet Suburban Area*Clean & Comfortable * Personal entrance with privacy**5 minutes from Christiana Mall*Free parking next to the entrance with large driveway* Park views. Near I-95 and Rt-1 and all major highways**Convenient & affordable for 1 night or more. *Queen bed/full kitchen/Large TV/Quality appliances Located in cul-de-sac/Free Wi-Fi and YouTube TV /Keurig coffee maker. Lower level Apt. Everyone is welcome. I hope you enjoy your stay!!

Relaxing Ranch Getaway near Christiana Mall & Univ

Charming 3BR/2BA ranch retreat in Bear, DE! Perfect for families or business travelers, this home comfortably fits your group. Features a custom kitchen, cozy fireplace, deep soaking tub, and a large, fully fenced-in backyard. Just minutes from the University of Delaware, Christiana Mall, and major corporate offices. Enjoy high-speed WiFi and dedicated parking. (You will need to provide government-issued photo ID to us and a $1,500 security deposit may be charged at the host's discretion)

"The Townsend" - Hot Tub!

On the way to The Townsend, you'll pass roadside farmstands and open fields. This meticulously restored farmhouse, located on the Cohansey River, features waterfront views in every room in the house so you can unwind, reflect and enjoy the company of family and friends. Outside you'll find a fire pit, hot tub and large field, perfect for outdoor activities. A quick 3 mile drive takes you to the historic town of Greenwich. Please read "the space" section, which gives room-by-room detail.

King Bed - Center of Historic District

This cute 1 bedroom apartment is located at the HEART of our lovely town. Steps away from some of the most historic places in the entire United States. Come near the weekend and you can tour our informative museums and wayside exhibits while taking in the local culture. We are a close-knit town and are happy to show out-of-towners "the way". On days we are open enjoy a $15/day credit to our cafe next door. Please enjoy your stay! We are so sorry but no pets allowed.

Long Beach Cottage, Hot Tub, Beachfront

The cottage is waterfront and is a PERFECT spot for a romantic couple's getaway! honeymoon/celebrations Designed with that in mind, a kitchen w/ espresso machine, living room with wood burning fire and a romantic luxurious suite with a king bed & cozy ambiance complete w/ water views and a stunning bathroom that features a double vanity, a large soaking tub, a tile shower with a soothing 3 function rain shower is complete with luxury linens, cozy robes & soft towels...

Delaware City Oasis|Indoor Heated Pool

Delaware City Oasis, is a premier luxury property that is truly one of its kind in the entire state. The Oasis is a serene and picturesque retreat nestled in the heart of Delaware City, Delaware. This hidden gem offers an escape from the hustle and bustle of everyday life, providing a perfect blend of modern amenities. As you enter the Oasis you are greeted by 5000 sq ft including a Great room with a heated indoor pool making this home prime for entertaining.

Bohemia Bungalow

Experience this charming 1940's cottage nestled on bustling Bohemia Avenue in the heart of picturesque Chesapeake City. Enjoy porch-sitting "on the Avenue", or visit numerous local eclectic shops, restaurants, a brew pub, and even a yoga studio, all only steps away. Marvel at massive cargo ships navigating the C&D Canal, just a 2-minute walk from your doorstep. Private off street parking for 2 cars.

Green Sanctuary-Pvt Apt for Quiet Rest

Green Sanctuary is the second floor apartment B in a two unit apartment building. It is a bright cheerful one bedroom unit with a large covered balcony located on the grounds of the famous Egyptian house. The apartment is comfortable for 2 people but will accommodate 4 with the living room couch converting to a bed. The property is conveniently located with plenty of off street parking.

Coastal Living in Delaware City

Nestled in the heart of historic Delaware City, this charming home offers serene coastal living with modern amenities. Enjoy spacious rooms, scenic views, and a quiet small-town atmosphere, all within walking distance to the waterfront and local parks. With its blend of historic character and contemporary updates, this home is a perfect retreat for those seeking both comfort and charm.