Vacation Rentals in Lewes

Plan a vacation at the historic seaside town of Lewes set upon the confluence of the Delaware Bay and the Atlantic Ocean. Lewes is Delaware’s first European settlement with strong Dutch roots, and the town’s landmark residences, lightships, towers, and museums are testament to its momentous past. History fans, culture trippers, and nature enthusiasts alike will have much to do from scouting old lightships and defense outposts to enjoying the windswept landscapes. Book a vacation rental on Holidu and let the sightseeing begin!

The blissful town of Lewes has vacation rentals that cater to all tastes and sensibilities. Many come equipped with amenities such as outdoor pools, patios, kitchens, and even direct beach access which means you can wake up to the sound of the waves and gaze into the sea right from your bed! Rentals in downtown Lewes are a good idea thanks to proximity to cafés, bars, and landmark attractions. You could also stay at the charming res0rt town of Rehoboth Beach. Waterfront vacation rentals are aplenty, and everyone from families with kids to solo travelers and groups of friends will find what they’re looking for.

A good starting point to get a feel of the town is at the Lewes History Museum. There are scores of old photographs, artifacts, paintings, and documents here. The museum also hosts the Children's Discovery Center where kids go crazy checking out the lighth0use model, fog horn, and reflecting lights. Delaware’s maritime and colonial past unfolds at the Zwaanendael Museum. The building’s picturesque exterior replicates the appearance of a typical Dutch residence, and exhibits on early Dutch settlements are riveting. Finally, don’t miss a photo op in front of the cannonball that lies affixed (still!) to the spot it landed on at the Lewes Maritime Museum. This small downtown museum is packed with interesting information tidbits on lighth0uses, pirates, and the likes.

Downtown Lewes has quite a few outfitters who’ll help you rent stand-up paddleboards and tandem kayaks. These are a great way to get a feel of Delaware’s waterways. Next is to enjoy a sunset stroll at Rehoboth Beach’s iconic boardwalk – there are tons of sea-facing cafés and bars nearby. Rent a car and drive to Cape Henlopen State Park. Diversions here include bird-watching at the Point Overlook, fishing along the scenic pier, beautiful sunsets, and best of all, the chance to bike through magnificent wetlands and dunes at the park’s Gordon’s Point Trail. While here, do visit the Fort Miles Historical Area, a strategic defense post during World War II. Take their docent-led tour up the tower and pause a moment to take in endless ocean views.

Each season in Lewes brings its flavor of festivals and events. The Historic Lewes Farmers Market features friendly vendors who sell everything from freshly laid duck eggs to organic meats and baked vegan delights. A unique event is the Mid-Atlantic Sea Glass & Coastal Arts Festival that takes place in May. This family-friendly affair unites coastal artists who come together to showcase their sea glassworks. September features the Annual Outdoor Antiques, Vintage & Artisans Fair, an extravaganza of eclectic vintage items dating to different periods. Music and local eats and drinks add a festive touch. The year ends with a beloved holiday tradition, the Christmas Tour of Lewes where owners of 18th and 19th-century private residences, open their h0mes to the public. Expect Christmas bazaars, tree lighting, and bake sales too.

For a slice of Ireland in Lewes, try the Irish Eyes Pub, a local haunt for over 30 years now. Their lip-smacking pub food is generously portioned, and Happy Hours with live music are the perfect recipe for a fun night out. The nautical-themed seafood bistro, Striper Bites impresses with its crab bisque, conch fritters, and baked oyster preparations. For sumptuous fish tacos paired with a ruby red sangria, try the elegant Agave Mexican Lounge & Tequila Bar. Finally, satiate dessert cravings with an exquisite hazelnut chocolate truffle available at Edie Bee’s Confection Shop. The candy here is showcased in vintage-looking glass jars.

A short ride south of Lewes will get you to Funland, a family-owned amusement park in operation since 1962. The vibe here is decidedly nostalgic thanks to the carnival-type rides, vintage games arcade, and Haunted H0use.

There are lighth0uses and there are lightships! Well, here’s your chance to hop onboard the historic Lightship Overfalls museum ship that once shone a light for sailors lost at sea. This is the largest light vessel built by the US Lighth0use Service.

Lewes is an unabashedly tranquil town so if you’re in the mood to party until dawn breaks, head out to Dewey Beach. The town’s main street is abuzz with nightclubs and bars, and summertime is even more exciting – look forward to beachside concerts, outdoor movie screenings, and a fun festival line-up.

A top-rated attraction is the Cape May-Lewes Ferry ride between Delaware and New Jersey where you’ll be treated to views of old lighth0uses and harbors, dolphins, seabirds, and unique seafaring vessels. Tip: enjoy a waterfront meal at the Grain on the Rocks restaurant at Lewes Terminal – they have live music on some nights too.

This is a unique attraction where kids are outfitted in pirate garb - tattoos, face paint, eye patches, and more! The “cruise” takes place on a real pirate ship called the Sea Gypsy. Expect water cannon fights, song sessions, treasure hunts, and a genuinely passionate crew!