# We Stayed at Sideways Inn Buellton And Loved It *By James Hills — Updated August 2026* Fans of Sideways will immediately recognize the iconic "Windmill Inn" located in Buellton, CA. In the movie though, the motel that Jack and Miles stayed in was a budget property that wasn't really all that desirable. Up until a few years ago, that was still true. Thankfully the property was purchased by Highway West Vacations - known for buying affordable west coast properties and bringing them up to a level that would be considered chic while still maintaining an affordable price point. While I've wanted to stay here for many years, I finally got the opportunity to do so on our recent tour of Santa Ynez Valley wineries. Our room was 134, directly below room 234 where Jack and Miles stayed. While there have been some changes to the layout as they updated the property, [Sideways Inn](https://sidewaysinn.com/) is still very identifiable as the motel from the movie. This includes the famous windmill which serves as the location for check-in as well as a small convenience store where you can grab snacks as well as local wines - including of course Hitching Post Wines. ### Las Vegas or Dubai - Which Is Better For A Bachelor Party If you are planning a destination bachelor party, Dubai and Las Vegas are top choices, here's which one you should pick. ManTripping [Read More](https://ads.flowmediamarketing.com/go/1hSkTtgHUPmTy1Sd7n5JEg.1103) ### What To Expect on Your First Viking River Cruise Here's what to expect on your first Viking River cruise through Europe including a personal experience exploring Christmas Markets along the Rhine. ManTripping [Read More](https://ads.flowmediamarketing.com/go/1hSkTtgHUPmTy1Sd7n5JEg.1040) ### Kadún Hotel Boutique Experience design suites, artisan dining, and premium lifestyle amenities in the heart of Cabo San Lucas. Walk to Medano Beach and the Marina boardwalk. 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Similarly, instead of having a standard continental breakfast, they offered a daily breakfast bag that would appear on your door handle every morning (assuming you filled out the form the night before). Even better is that since they are pet-friend, you can even get treats included in your bag for your dog too. I'm not entirely certain if these elements are just a COVID policy, but I look forward to improvements like this to continue.  ## Man Gear Pick of the Month November's Pick Amazon (affiliate) ### COROS Pace 4 Pro GPS Sport Watch Why we picked it: a screen big and bright enough to double as a photo frame, a titanium and sapphire build that came through a month of daily wear without a scratch, and battery life that still runs weeks between charges. 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While the bathroom was extremely basic, I appreciate the design of the room as something that is perfect for a wine weekend getaway.  Outside the first floor rooms in the main building, you have a patio that is perfect for relaxing with a bottle of wine and it walks out to the pool area as well. Just as in the movie, Sideways Inn is close to everything in downtown Buellton and is located just off the highway. While I'd recommend driving or taking a Lyft vs walking to Hitching Post Wines, it is only a few minutes away along with a cluster of several tasting rooms including DorWood Distillery, Alma Rossa Winery, and McClane Cellars. Based on our experience staying at [Sideways Inn](https://sidewaysinn.com/) I am very excited to check out some of the other Highway West Vacations properties of particular interest are two properties in Borrego Springs, California that would make a perfect home base for some offroading. Details Written by: James Hills Last Updated: 13 August 2026 ### 🚢Ready To Book A Vacation? Let us help you plan a cruise, all-inclusive resort, or tour for your next guys trip, family vacation, or romantic getaway. Click here to [**Book Your Next Vacation**](https://www.mantripping.com/vacation-planning.html). #### Is Your Money Better Spent on Lobsters and Beer Than a Week Glued to Cruise Ship WiFi? 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