Planning a Summer Vacation to Rehoboth Beach, Delaware

Our recent trip to Southern Delaware was full of joyful surprises. If you live in Maryland or Washington D.C., then the wide, flat sand beaches that stretch for miles are likely no surprise. Similarly, you won’t be shocked by the cute boutiques, good restaurants, and gorgeous summer homes that line the streets of Rehoboth Beach. But, those that live outside of that 200 mile radius may have overlooked this little gem in favor of some of its more famous neighbors to the North or South. Well I hope they don’t mind too much if I let you in on that little secret, because this is one stretch of beach that should not be overlooked and there are so many things to do in Rehoboth Beach and the surrounding area.

First, let me give you the lay of the land. Southern Delaware has five major beach towns: Lewes, Rehoboth Beach, Dewey Beach, Bethany Beach and Fenwick Island. Each has its own distinct character so first you want to pick the one that best matches your style.

Cape Henlopen beach Delaware

Cape Henlopen State Park Beach

Southern Delaware beaches

Lewes — Lewes (pronounced Lewis, as I was corrected), holds the honor of being the first town in the first state. This history is evident from its quaint downtown streets lined with leafy trees and historic homes with their colorful flower boxes overflowing with blooms. Connected by ferry to Cape May, New Jersey, there is also plenty to do for families from kayaking, paddle boarding, fishing and more.

Rehoboth Beach — South of Lewes is the upscale beach town of Rehoboth Beach. While it still sports a family-friendly boardwalk with arcades, rides, and plenty of junk food, it is quite different from Ocean City, Maryland, its larger southern neighbor. The main street offers a good selection of stylish eateries and cute boutiques. There are a few motels but this is primarily a beach rental community, with some enormous homes along the beach road that are clearly executive summer homes.

Dewey Beach — The next town down is Dewey Beach, which has an entirely different vibe from the other beach towns in Southern Delaware. This is clearly the party town, with basic surf shops, motels, and beach bars. But it also has the gorgeous Delaware Seashore State Park, with access to both Rehoboth Bay and the Atlantic Ocean.

Bethany Beach / Fenwick Island — Known as the “Quiet Resorts,” Bethany and Fenwick are the last stop before crossing into Ocean City, Maryland. Bethany is similar to Rehoboth, just smaller and with a less commercial boardwalk. Also more of a vacation rental town, there is now one nice-looking hotel, the Bethany Beach Ocean Suites.

We visited Southern Delaware in early June and, except for some windy days, the weather was perfect and, since the local kids were still in school, there were no crowds! It really made it the ideal time to be there and explore all the things to do in Rehoboth Beach.

Your ultimate guide to planning a summer vacation in and around Rehoboth Beach, Delaware including things to do in Rehoboth Beach and the other Southern Delaware beaches.

Where to Stay in Rehoboth Beach

Crosswinds Motel Rehoboth Beach Delaware sign

If you are staying for a week, a vacation rental is probably the way to go. Since we were in town for only four days, and it was just the two of us, it made more sense for us to get a hotel room. We stayed at the Crosswinds Motel right on Rehoboth Avenue, the main strip in Rehoboth Beach. Our double room on the second floor was surprisingly quiet. I’m usually not a fan of motels for safety and comfort reasons, but the Crosswinds’ rooms face the interior parking lot, versus the street, and they were surprisingly comfortable. Clearly the property has been recently renovated in a modern style with all your basic comforts including a flat screen TV and large vanity area. The air-conditioning unit blocked out any exterior noise and the wood laminate floors were perfect for a beach motel. The best thing about the Crosswinds was the location. It was a five to ten minute walk to the beach and boardwalk and just steps to some great restaurants.

Crosswinds Motel Rehoboth Beach Delaware

Crosswinds Motel

We loved our time in Rehoboth Beach and, just like our other mother-daughter trips, we found spending quality time together and engaged in activities side-by-side a wonderful bonding experience, can’t you tell?

Mother-daughter trip to Rehoboth Beach Delaware

Girls only road trip shirts


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3 Comments on “Planning a Summer Vacation to Rehoboth Beach, Delaware

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  1. You packed a lot into your four-day trip. We live locally and you have yet to do some of the things you mention in your post. Kayaking and Cape Water Taxi is on our to-do list. Thanks for the great ideas.

    My favorite beach since childhood! Looks like you guys really had a great time. Some of my family tried the Escape Room last weekend and loved it! Tried to go to the Crooked Hammock on a Saturday night but it was too busy.

      I’m happy we finally got to experience it. I’ll definitely want to go back. We went early to crooked hammock and it was still packed — fun place though. Now I want to do another escape room at home — I was surprised how much fun we had there.

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