Vacation rentals in Port Penn

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Top-rated vacation rentals in Port Penn

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
Home in New Castle
4.95 out of 5 average rating, 20 reviews

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!

Top guest favorite
A spacious living room is presented with natural light streaming through large windows. Minimalist furniture includes a comfortable sofa and two accent chairs. A round coffee table is centrally located on a patterned area rug, complementing the neutral color palette of the room.
Home in Bear
4.97 out of 5 average rating, 29 reviews

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.

Top guest favorite
Home in Newark
5.0 out of 5 average rating, 20 reviews

Stunning Farmhouse near Christiana Mall Newark, DE

The whole group will enjoy easy access to everything from this centrally located place! 10- 15 minutes walk to ALDIs, Planet Fitness Gym, Red Robin’s Restaurant and many other stores and restaurants in same shopping center! 2 minutes drive to Wawa, and Chick-fil-A! A minute walk to nearest bus stop! 5 minutes drive to Christiana Mall, Costco and many more shopping places! 15 - 20 minutes drive to University of Delaware and Christiana Hospital! 35 - 40 minutes drive to Philadelphia!

Top guest favorite
A sailboat glides across the water during sunset, with the sun casting a warm glow over the surface. Silhouetted trees frame the scene, enhancing the serene atmosphere of the evening along the Chesapeake Bay.
Cottage in North East
5.0 out of 5 average rating, 65 reviews

Vintage Waterfront Cottage with Stunning Sunsets

This unique Red Point Cottage offers vintage charm, rustic accents and incredible sunsets overlooking the Chesapeake bay from a 50 ft cliffside waterfront location. Our cottage has two bedrooms, one queen and one king - all bedding is provided and included. We have an open cottage concept with water views from every room. A stone gas fireplace, fully equipped custom kitchen, central air, washer & dryer, WIFI, flat screen TV, stereo, gas grill, fire pit, outside shower and front porch.

Top guest favorite
Cottage in Charlestown
4.96 out of 5 average rating, 293 reviews

Long Beach Cottage, Hot Tub,Wood Burning Fireplace

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...

Superhost
An open living space features a dining area with a round wooden table and three chairs. A comfortable seating area includes a dark couch and a patterned rug. Natural light enters through the sliding door, which leads to the outdoor balcony. Decorative elements include a plant and artwork on the wall.
Townhouse in Middletown
4.87 out of 5 average rating, 87 reviews

Spacious 3 bed/1.5 bath townhome with free parking

Relax in this lovely 3 bedroom, 1.5 bath townhome with free parking on premises. This home is close to parks, beaches, fine dining, bowling, art activities, theater, walking trails & much more. The home has ample space for you and your family to enjoy. There is a full kitchen, living and dining area, laundry room, 3 bedrooms and a balcony. There is opportunity for short stays and longer stays.....send us a message. Don't forget Tax-Free shopping in Delaware!

Superhost
An aerial view showcases the expansive layout of the Delaware City Oasis. The property features a spacious exterior area, highlighted by a large deck and a well-maintained lawn, surrounded by mature trees. Ample parking space is visible along the winding driveway.
Home in Delaware City
4.89 out of 5 average rating, 70 reviews

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.

Guest favorite
Condo in Newark
4.92 out of 5 average rating, 50 reviews

Quiet condo near Christiana, UD, Wilmington | Desk

✨ Spacious Newark Getaway Near Christiana & UD Welcome to your home away from home in the heart of Newark, Delaware! 🌿 Our peaceful and secluded retreat is tucked away in a quiet neighborhood yet just minutes from Christiana Hospital, Christiana Mall, the University of Delaware, and downtown Wilmington. Whether you’re visiting for work, family, or leisure, this bright and spacious home is designed for both comfort and convenience.

Top guest favorite
A spacious living area is presented with a light-colored wall and high ceiling. Seating options include a green recliner and a brown sofa, both arranged around a soft area rug. A flat-screen television is positioned near a coffee table, and a doorway leads to additional rooms.
Loft in Bridgeton
4.98 out of 5 average rating, 271 reviews

Beautiful newly updated apartment in Fairton.

Forget your worries in this spacious and serene space. This recently renovated second floor apartment boasts natural light and nature at your footsteps. It has every comfort needed to feel like you're right at home. It is conveniently located close to New Jersey Motor Sports Park and the Delaware Bay. It has plenty of space to park large trailers and boats. NO SMOKING PET FRIENDLY (pets must be clean)

Top guest favorite
A welcoming porch features white adirondack chairs and a small blue table. A lantern and a decorative container are placed nearby, with the house's yellow exterior and orange shutters providing a cheerful backdrop. The view includes trees and street activity.
Cottage in Chesapeake City
5.0 out of 5 average rating, 131 reviews

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.

Guest favorite
The front exterior of a charming, single-story home is presented with white siding and black shutters. A welcoming porch with classic columns leads to the entry, flanked by greenery and flowering plants. The well-maintained lawn complements the inviting entrance.
Home in Delaware City
5.0 out of 5 average rating, 19 reviews

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.

Guest favorite
The exterior of the two-unit apartment building is presented, showcasing a covered porch with seating and steps leading to the second floor. Surrounding grassy areas and trees contribute to a serene atmosphere, with fields visible in the distance.
Apartment in New Castle
4.87 out of 5 average rating, 476 reviews

Blue Tranquility-Pvt Apt for Quiet Rest

Blue Tranquility is the first floor apartment (apartment A) in a two unit apartment building. It is a cozy one bedroom unit with a large covered porch located on the grounds of the famous Egyptian house. The unit 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.

Popular amenities for Port Penn vacation rentals