
Winston Waterways Holidays
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Your Winston Waterways Holiday
Planning your next travel adventure just got a lot easier with a holiday package to Winston Waterways. Immerse yourself in the very best this neighbourhood has to offer while creating fond memories you'll replay for years. Begin your trip to Winston Waterways by visiting nearby attractions such as Jimmy Johnsons Big Chill, John Pennekamp Coral Reef State Park and Caribbean Club Bar. Don't just imagine it — make it happen! Book your perfect Winston Waterways holiday with Expedia and experience travel your way.
Our guide on where to stay in Winston Waterways

Rock Harbor
While there might not be top attractions in Rock Harbor, you can explore the larger area and discover places like Bluefin Rock Harbor Marina and Jimmy Johnson's Big Chill.
Our pick of the best Winston Waterways Hotel Deals

Chesapeake Beach Resort
Very clean and nice. Not a 5 star resort. But nice. Breakfast was good
Reviewed on 11 Jan 2026

Marina Del Mar Resort and Marina
Our room was huge and Clean. We arrived early and our room was ready. Saw a manatee in the Marina as well as a nurse shark. Plenty of pelicans to watch and great food and entertainment on the premises.
Reviewed on 12 Jan 2026

Waterside Suites & Marina
We just needed a short stay this time, but everything was wonderful.
Reviewed on 9 Jan 2026










