Vacation rentals in Port Penn

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Top-rated vacation rentals in Port Penn

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Top guest favourite

Townhouse in Middletown

5 out of 5 average rating, 32 reviews

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.

Guest favourite

Home in Bear

4.92 out of 5 average rating, 24 reviews

Relaxing Ranch Getaway near Christiana Mall & Univ

This charming ranch house in Bear, Delaware is the perfect place to unwind and explore the area. Whether you're in town for business (JP Morgan Chase is nearby!) or a visit to the University of Delaware, our comfortable 3-bedroom, 2-bathroom home provides a relaxing retreat. Enjoy high-speed WiFi, and close proximity to Christiana Mall for all your shopping needs. (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)

Superhost

Apartment in New Castle

4.67 out of 5 average rating, 6 reviews

Cozy Apartment Outside Historic Old New Castle

Enjoy this 1 bed/1 bath home away from home. Kick your feet up in front of the fireplace and watch your favorite shows. Minutes drive away from Historic Old New Castle with coffee shops, library, restaurants, and more. Enjoy a stroll along the Delaware River at Battery Park, and be a part of all this beautiful town has to offer. Super convient location 3.4 Miles to Wilmington airport 27 Miles from Philadelphia Airport 8.6 Miles from Christiana Hospital 6 Miles to City of Wilmington and more.

Guest favourite

Home in Bear

4.95 out of 5 average rating, 42 reviews

Modern, Spacious & Great Location

Welcome to Blue Hen Haven! Enjoy a peaceful stay in our newly renovated 4-bedroom home. Our spacious and well-equipped home is in a peaceful neighborhood for work-related duties or maximum relaxation. Blue Hen Haven has comfortable bedrooms, spacious living & dining areas, a dedicated workspace, and outdoor furniture with a firepit for relaxing outdoors. The house offers a fully equipped open kitchen/dining room, and a washer and dryer. Follow us on IG @bluehenhaven for area events and more.

Top guest favourite

Guest suite in Newark

4.99 out of 5 average rating, 146 reviews

Charming Fully Equipped Private Guestsuite

Relax in a stylish guesthouse in a quiet, safe neighborhood. Its private entrance and parking for 2 vehicles makes the cozy space all the better. Enjoy the full kitchen, work space, high speed internet (1200mbps), 50” TV, full bathroom, and more. Perfect for the business professional on-the-go, or getaway. Take a stroll through White Clay Creek Park with your furry friend. Just a short 5 minute drive from Main St.'s restaurants, local bars, and UD. Only 10 minutes from Christiana Mall.

Superhost

Home in Delaware City

4.87 out of 5 average rating, 52 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 favourite

Home in Salem

4.96 out of 5 average rating, 109 reviews

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 backdoor directly onto the large deck and sandy beach. Message us for information about the local wineries and distilleries or for kayaking!

Top guest favourite

Apartment in Chesapeake City

4.97 out of 5 average rating, 38 reviews

Private entrance King Suite

Forget your worries in this spacious and serene space. Brand new private room on historic waterfront Chesapeake City Farm. You will have a private entrance to your roomy king suite, complete with luxurious bathroom, kitchenette efficiency, and coffee bar. You will have access to the Bohemia River, and a 200 acre horse farm, where wildlife abounds and the views are spectacular.

Superhost

Apartment in New Castle

4.88 out of 5 average rating, 427 reviews

Blue Tranquility-Pvt Apt for Quiet Rest

Blue Tranquility is the first floor apartment 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.

Top guest favourite

Home in New Castle

4.98 out of 5 average rating, 41 reviews

Water View Historic B & B - Gift Card Included

Enjoy sunrises over the Delaware River while you relax on your screened in porch and private backyard in beautiful Historic New Castle, Delaware. A truly one-of-a-kind property awaits you! Every stay includes a gift card to our cafe down the street! The Mercury features coffee, tea, cocktails, vegetarian cuisine and an opportunity to meet the locals!

Top guest favourite

Cabin in Greenwich

4.92 out of 5 average rating, 232 reviews

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. Firewood included! The separate seven-person hot tub is OPEN for the season. The private pool + built-in spa is closed and is set to reopen mid May 2025

Top guest favourite

Home in Newark

5 out of 5 average rating, 37 reviews

Bohemian Minimalist Haven

A peaceful Newark escape—perfect for solo travelers, couples, and small families. Just 15 mins from the University of Delaware and near Christiana Mall. Pet-friendly with bohemian-minimalist charm, a native garden, and a cozy work nook. Ideal for quiet stays, weekend resets, and remote work. No parties—just calm energy and curated comfort.