5 Local Bars and Restaurants Where You Can Spend the Night

A fun way to support local bars and restaurants.

Do you miss happy hour at your favorite bar? Arriving for a coveted Saturday-night dining reservation? Due to decreased-capacity orders during the COVID-19 pandemic, those two activities are – for many – on hold.

But if you still want to lend your financial support to local bars and restaurants, there is a way. Have you thought about checking in for the night?

From a Riverwest Tiki institution to a West Allis German-style fish-fry spot, its owners have unleashed a new source of revenue by opening up upstairs spaces to guests hungry for a new experience beyond a typical hotel stay. Much like an apartment – these are listed on Airbnb – you have access to a kitchen, a living space, a bedroom and, most importantly, a new view. Plus, they are managed by the bar’s or restaurant’s owners, giving them cash flow to ride out the pandemic.

1. Cactus Club’s Greenroom Cabin


When this famed live-music venue got a new owner (Kelsey Kaufmann) in February of 2020, lots of changes were made to roll with the pandemic’s halt on shows, such as hosting food trucks parked out front, plus crafters/artisans and florists, along with a line of logoed apparel. This also includes opening up the upstairs – where bands used to stay – to the public. The two-bedroom, one-bath pad adorned in a ‘50s vibe (wood paneling and a rotary phone are two props) is fresh off a February 2020 remodel and any reservation also gets a complimentary tour of the club (backstage included), and an option to add on a drinks package.

2. Boone & Crockett’s The Castor House


Decked out with URSA’s desert-modern styling (fringed throw blankets and Southwestern-style embroidered rugs and pillowcases), the loft within Castor House (above Boone & Crockett’s bar) is a nod to Milwaukee’s architecture thanks to walls of exposed Cream City brick. But there’s also a rattan peacock chair, hammock and potted cacti. Although technically one bedroom, the loft is spacious enough to sleep six people due to pull-out couches and also includes a kitchen. 

3. Kegel’s Inn


Just think about it: when the weather warms, your bed could be a walk upstairs from the beer garden! Kegel’s Inn’s fourth-generation owners Julian and Stephanie Kegel (Julian’s grandfather, George, operated the restaurant during the 1950s and 1960s) offer three studio apartments above the restaurant for nightly rentals, featuring original 1930s tile in the baths and exposed wood beams in the living spaces. Need a little more room to spread out? There’s also a two-bedroom apartment.

4. The Foundation’s Captain Quarters


Particularly during the winter months, the stark contrast of a Tiki-fied ambiance is very noticeable upon entering The Foundation. A newer amenity is the two-bedroom Captain Quarters for overnight stays, rolled out in 2017, and taking the downstairs bar’s South Seas theme to the next level. Instead of sharing The Foundation’s bar with other patrons, you have your own private bar in the space – decorated with wood carvings, pufferfish lights and rattan. The bartender is not included, but ceramic tiki mugs are.

5. Shaker’s Cigar Bar’s Haunted Penthouse


The main appeal of this 1,400-square-foot pad above the cigar bar is that the building is reportedly haunted, a fact that staff are very open about. Don’t say you weren’t warned – and pack your ghost-hunting gadgets! And this particular apartment is inhabited by a dead hooker. Regardless of whether you believe in paranormal activity or not, it’s a fact that the Capone Bros. used to hang out here when it was a brothel. Because tours of this building are often run, check-in happens at an odd hour (11 p.m., after the last tour, included in the nightly rate).



A seasoned writer, and a former editor at Milwaukee Home & Fine Living, Kristine Hansen launched her wine-writing career in 2003, covering wine tourism, wine and food pairings, wine trends and quirky winemakers. Her wine-related articles have published in Wine Enthusiast, Sommelier Journal, Uncorked (an iPad-only magazine), FoodRepublic.com, CNN.com and Whole Living (a Martha Stewart publication). She's trekked through vineyards and chatted up winemakers in many regions, including Chile, Portugal, California (Napa, Sonoma and Central Coast), Canada, Oregon and France (Bordeaux and Burgundy). While picking out her favorite wine is kind of like asking which child you like best, she will admit to being a fan of Oregon Pinot Noir and even on a sub-zero winter day won't turn down a glass of zippy Marlborough Sauvignon Blanc.