We are heading to Ventura in early June for a family event. Would like upscale accomodations...how about the Pierpont Inn? Also, what about day trips, wineries, etc. Weather will be cloudy and cool, right? Thanks.

Pierpont was tired when we were there a few years back but I think they may have upgraded/renovated. It's right on the freeway though.

Take a look at Embassy Suites or Mandalay Shores Resort in nearby Oxnard.

I would too suggest Embassy Suites,but also the Four Points, or Ventura Marriott. I haven't stayed at Embassy but have the other 2. They were nice, with the Marriott being the nicer of the two; however, the Four Points is on the water. Unfortunately, I wouldn't call any lodging in that vicinity "upscale" but the rooms are nice in the Marriott. Hope that helps!

I forgot to comment on the weather.. it is generally foggy in the AM but warms up around 11 or so. It will not be hot, more like 75. It of course will be a little cooler along the ocean.

Ventura is a nice little treat of a town and Ojai and Santa Barbara and convenient to visit from there.