Vacation rentals in Port Penn

Work crews and families, short drive to MD and PA

✔ Spacious open floor plan ✔ Outdoor dining ✔ Quiet neighborhood ✔ 5 beds total with optional twin in 1st-floor bedroom ✔ 30+ day stays welcome ✔ 1 GB Wi-Fi ✔ Dedicated workstations in each bedroom ✔ 5 Smart TVs - Master has a 55"TV ✔ In Unit Laundry ✔ Fully Stocked & Equipped Kitchen ✔ Garage Access for storage ✔ Off street parking for two oversized vehicles ✔ Street Parking ✔ Prime Location: Go to "Neighborhood Highlights" to view nearby hospitals, schools, places to visit, etc.

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!

Luxury Townhome w/free parking

Welcome to this luxurious, updated and stylish home that is centrally located, yet tucked away in a peaceful area with inside & outside dining. This 2 bed/1.5 bath home is has beautiful lighting, laminated floors, high ceilings, large rooms w/king bed & comfortable sofa for reading or relaxing in the master bedroom. The second room has 2 full beds. The kitchen is updated with all the necessary appliances and utensils that even a chef would enjoy and flows into the classy living/dining area.

Connection Pointe•River views•Quiet•Peaceful

Connection Pointe is a great getaway for your family vacation or to reconnect with friends, you will be sure to enjoy this beautiful property that sits right along the Sassafras River, it is quiet and peaceful with amazing views from the house and the screened in deck. Come enjoy the sounds of nature as you take time to relax and refocus! There is no boat access to the river from the property. There is a fairly steep bank going down to the river, so please be mindful of this with children.

Chesapeake City Charm at the Boho House!

Welcome to the Boho House! This is a newly renovated three bedroom custom home located in charming historic Chesapeake City. Enjoy some of the best restaurants the area has to offer just steps from the front door. This home is beautiful inside and out, features a welcoming kitchen and family room space, two off street paring spaces ,out door patio and grill and a wonderful front porch to sit and relax. Perfect for wedding stays, weekends away and or local event stays.

The Pearl: A hip & cozy canal-side apartment

The Pearl is a 2nd floor apartment 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,full kitchen,etc. It's got a 70s vibe, an eclectic combo of euro/scan/boho hip! Come stay with us, you won't regret it!

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.

Perfect Getaway | Close to Philly & Wilmington!

Unwind and create lasting memories at this serene and inviting 4-bedroom, single-family home. Nestled in a prime location, our beautifully renovated space offers the perfect blend of comfort and convenience for families, friends, or groups. With nearly 1,750 sq. ft. of spacious living, this charming getaway features separate living and family areas, giving everyone room to relax after a day of exploring local attractions or coming back from work or business.

Beachfront Sunsets on the Water at Oakwood Beach

You’ll instantly relax when you arrive at this private beachfront home on the beautiful Delaware River (2020 River of the year!). This hidden gem is off the beaten path, making it perfect for you to escape the hustle and bustle of your busy day-to-day. You’ll love the amazing sunsets and water fun — walk out the back door directly onto the large deck and sandy beach. Message us for information about the local wineries and distilleries or for kayaking!

The Hepburn-Hot Tub & Fire Pit

The Hepburn is a beautifully renovated and decorated by home by Harlow Grey Homes. This meticulously restored glass cabin is located on over an acre of private grounds on a serene 75 acre lake. This is not a home for parties, loud events. The 10pm QUIET HOURS outside is mandatory! The separate seven-person hot tub is OPEN for the Fall/Winter season when the pool is closed. The private pool + built-in spa is open Spring/Summer

McReynolds-Woods House -Private 3 Bedroom Home

Enjoy this private home located on the South Side of Historic Chesapeake City C.1870. The property is walking distance to dining, shopping & local attractions. Stroll around town, enjoy the beautiful views or spend time relaxing on the porch. Small dogs allowed (two only under 25 lb.). We have a small fenced yard which is nice for the little ones and there is off-street parking in driveway on side of the house.