Rehoboth Beach, Delaware, is famous as America’s top summer getaway, but its charm shines just as brightly during the holiday season. As the weather cools and festive lights twinkle along the coastline, this beach town transforms into a winter wonderland, offering a unique blend of holiday spirit and coastal beauty. My son and I had a fantastic weekend getaway filled with memorable experiences.  The warm hospitality from locals made us feel right at home. 

Rehoboth Beach offers something unique whether you’re looking to relax, shop, or indulge in delicious cuisine. For a range of activities, check out the Visit Delaware website.

Traveling to Rehoboth Beach from Chicago

Getting to Rehoboth Beach from Chicago was a breeze, making it an ideal holiday getaway. We flew into Philadelphia from Chicago, a quick 1-hour and 20-minute flight. We picked up our rental car from the airport and started our two-hour journey to Rehoboth Beach. 

Along the way, we stopped in Dover, Delaware, for lunch at the Grey Fox Grille and coffee from The House of Coffi.

Driving into Rehoboth Beach, we were immediately in awe of the coastal town, admiring the homes and shops lining the main streets. The weather was perfect for strolling and exploring!

Enchanting Experiences Await:  Things to Do

Step into a Winter Wonderland at Schellville Village

One of the highlights of the holiday season in Rehoboth Beach is Schellville Village. This festive wonderland features enchanting light displays, holiday decorations, and activities for all ages.

Donovan and I let our inner child run wild as we explored the miniature houses and town buildings.  We spent hours there engaging in all the activities, including train rides, snow zones, sledding, shopping, playing in the magical snow that falls for 15 minutes each hour, and listening to live music.  There are also many delicious food and drink options, with vendors lining the grounds.

Above all, Schellville’s Enchanted Winter Celebration is always free, making it accessible to everyone. They even have quieter hours to accommodate young children, seniors, and kids with noise sensitivities, ensuring everyone can make magical holiday memories.

This place is a dream!

Shop ‘Til You Drop with No Tax!

Rehoboth Beach is known for its tax-free shopping, making it a shopper’s paradise. Stroll through the quaint boutiques and specialty shops along the main streets, where you can find unique gifts and handmade items. There’s also the Tanger outlets, an expansive retail outlet with over 100 stores in three locations along the easily accessible Coastal Highway. I was excited about tax-free shopping because Chicago has a 10.25% sales tax. I’d much rather spend that money on more items for myself.

If you’re in the mood to shop, Rehoboth Beach is the place to be!

Take a Scenic Stroll on the Boardwalk

Even in the chill of winter, a stroll along the Rehoboth Beach Boardwalk is a must. The crisp ocean air and stunning views create a serene atmosphere. Enjoy the beautiful beachfront, take in the holiday decorations, and stop by a cozy café for a warm beverage. The boardwalk provides a perfect backdrop for holiday photos and cherished memories.

We visited the same weekend as the Santa Bar Crawl and were surrounded by 3,000 Santas on the boardwalk. The atmosphere was electric, filled with joy, energy, and festive cheer! 

Join the Festivities:  Holiday Activities Galore

Throughout the holiday season, Rehoboth Beach hosts various festive events and activities. There’s always something happening, from holiday parades to tree lighting and winter festivals. Check the local calendar for events that coincide with your visit, and immerse yourself in the community spirit.

During our visit, we drove through the neighboring town of Lewes, Delaware, to see their annual light tour.  The lights are turned on every day throughout December from 5-9 p.m. There’s an online map that shares all of the participating decorated homes and businesses. We were mesmerized by the stunning displays and beautifully decked-out homes. I highly recommend adding this to your itinerary.

Unwind with Local Brews at Revelation Craft Brewery

I love spending time in a great brewery with good people, and we found the perfect spot to unwind on a Sunday afternoon at Revelation Craft Brewery. The cozy atmosphere made relaxing easy, and the warm and friendly conversations with patrons and staff added to the charm. They offer a fantastic selection of craft beers, including seasonal brews worth trying. Plus, there’s a food truck parked outside serving delicious pizza—what could be better? It’s ideal for kicking back, catching the game, or enjoying friendly chatter.

Visit the Rehoboth Art League

Art enthusiasts can visit the galleries and exhibitions at the Rehoboth Art League. The galleries are free to browse and are always open to the public.

Culinary Delights:  Where to Eat in Rehoboth Beach

After a day of exploring, you’ll want to indulge in some delicious local cuisine. Rehoboth Beach offers a diverse dining scene that caters to all tastes.

Crust & Craft

This eatery is known for its wood-fired artisanal pizzas and extensive beer list. It was the perfect casual dinner spot after our evening at Schellville Winter Village. Don’t skip the Buffalo wings here; they were fantastic!

Henlopen City Oyster House

For seafood lovers, Henlopen City Oyster House is a must-visit. The oysters are fresh, and their lobster Reuben was one of the best things I ate in 2024!  We enjoyed our lunch so much that my son begged to return the next day, lol.

Victoria’s Restaurant at the Boardwalk Plaza Hotel

For a more upscale dining experience, head to Victoria’s Restaurant. The restaurant inside the Boardwalk Plaza Hotel is beautifully decorated for the holidays and offers intimate dining with a view of the ocean and boardwalk. 

Bluecoast Seafood Grill & Raw Bar

Another fantastic option for seafood enthusiasts is Bluecoast Seafood Grill & Raw Bar. This restaurant focuses on fresh, local seafood and offers a relaxed atmosphere and a variety of dishes sure to please any palate.

The Fractured Prune

Don’t miss The Fractured Prune for a sweet treat! It is known for its warm, made-to-order yellow cake donuts. Customize your donut with various toppings to indulge your sweet tooth.

The Point Coffee Shop and Bakery

Visit The Point Coffee Shop and Bakery for a cozy breakfast or brunch. You can enjoy freshly brewed coffee, baked goods, and hearty breakfast options here.

Where to Stay in Rehoboth Beach

For accommodations, consider the Breakers Hotel. Located just a short walk from the beach and Boardwalk, this hotel offers comfortable rooms and a welcoming atmosphere. With its convenient location, you’ll be close to all the holiday activities and attractions, making it a perfect home base for your Rehoboth Beach adventure.

There’s no shortage of joy in this winter wonderland. So pack your bags and get ready to create lasting memories in Rehoboth Beach this holiday season!