Are those prices for bottles/cases...or glasses/bottles?
The prices are for bottles and cases. The price you can see for the Merlot Reserve is $24.99 a bottle and $269.88 for a case. The 'tastings' very in price and how the tastings are done vary from vineyard to vineyard.
At Round Barn, you get five tastings for $8.00 of any wine, beer, or their vodka, rum, and bourbon. If you buy three bottles of something, you get $5.00 off. This also varies from winery to winery.
You do get a generous pour for the tasting and they're not strict on the count. I ended up tasting 8 different things at Round Barn.