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!

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.

Inviting, comfortable & private suite near Univ.

Enjoy this comfortable, relaxing guest suite with a kitchenette in a desirable and quiet neighborhood in Newark. Close to Downtown and Main St, this is a great base to explore the area and the University. We are less than 3 miles from the University and Main Street. The suite is tastefully furnished in a neighborhood with mature trees. It is totally private, with a separate entrance and a keypad for self check in. Parking is available in the driveway. Truly a serene getaway!

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...

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.

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.

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)

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.

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.

Charming cottage on 50 acre Chester County farm

Frog Hollow Cottage is a newly renovated getaway located in the heart of the Chester County’s rolling farmland and equestrian community. Overlooking beautiful pastures, the cottage was formerly the large painting studio of Delaware Valley artist Peter Sculthorpe. The studio has been re-imagined as a peaceful retreat for families, friends and couples.