Vacation rentals in Port Penn

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!

Ideal for work crews and families, long term perks

✔ 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" ✔ 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.

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.

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!

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.

Willow Pond Manor | Private Mansion on 26 Acres

🏡 Willow Pond Manor: A Private 26-Acre Estate in Chester County Set on 26 private acres in the rolling hills of Cochranville, Willow Pond Manor is a countryside mansion built for gathering. A spring-fed pond with a fountain sits out front, open pastures roll to the tree line, and there's space inside and out for everyone to spread way out. With 6 bedrooms, 10 beds & room for 19, it's made for family reunions, multi-family trips, and big celebrations. Save it to your wishlist! ❤️

Bohemian Minimalist Haven

Thoughtfully designed Newark stay featuring bohemian-minimalist décor, warm natural light, and pet-friendly comfort. The home includes a fully stocked kitchen and a private washer and dryer for longer or more convenient stays. Enjoy fast access to the Christiana Mall/ Fashion Blvd., University of Delaware, and dining. Located in a modest and quiet neighborhood that’s practical, central, and easy to navigate, with two dedicated parking spots directly in front of the home.

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!

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.

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.