Most Romantic Overnight Packages at Milwaukee Hotels

Visit Milwaukee


Mid-February in Milwaukee (cue Valentine's Day!) might be chilly outdoors but several hotels can help you and your sweetie turn up the heat indoors with the help of special packages. Whether your style as a couple is more “Downton Abbey” (think Victorian, romantic and historic) or has edgy, artsy flair, there is a hotel just for you.

“Horsing Around” at The Iron Horse Hotel

Since this boutique hotel with industrial-chic accents (it’s in a former warehouse) opened in Walker’s Point in 2008, creative packages have been rolling out all year long, each in perfect pitch with the season. With the “Horsing Around” promotion, aimed at couples, you get a bottle of sparkling wine, a 60-minute couples massage, free valet parking, and either breakfast for two or the famed Route 66 brunch in Smyth (Saturday-night stays only).

A dream stay for Harley-Davidson riders and fans (Harley cycles are made in Milwaukee), the “Love the Ride” package carries a high price tag of $22,900 but includes some major goods. With the two-night stay in a suite, you also get a new, limited-edition 2016 Harley-Davidson Softail Slim S in Vivid Black, $500 worth of Harley gear, a themed in-room amenity, and a private tour of the nearby Harley-Davidson Museum.

This darling little nine room inn is attached to a café and located a block from Lake Michigan in Cudahy, a 20-minute drive south of downtown Milwaukee. Each room is named for a different wine region and some have soaking tubs with jets. With the “Luxury Romance Package,” couples receive rose petals artfully arranged on the bed, a $30 gift card for a meal in the café, and a sweet amenity of sparkling wine, Sheridan’s signature lavender cookies and truffles delivered to the room. The package can be booked with just one night’s stay.

If you’re there on a Saturday night, don’t miss the decadent Sunday brunch with $5 Mimosas and Bloody Marys.


Considered the Grand Dame of all Milwaukee hotels, this is the place where many famous musicians and U.S. presidents have stayed. Dating back to 1893, the hotel includes a top-floor bar and live-music spot called Blu, afternoon tea in the lobby, a glam meal of steaks and cocktails at Mason Street Grill, WELL Spa + Salon for massages and other treatments, and one of the world’s largest collections of Victorian art. Included in the “Romantic Retreat” package is a $50 gift card to use on food and drink at Café Pfister or the Lobby Lounge, overnight parking, and Champagne and chocolate-covered strawberries in your room.

A few years ago, the hotel launched an Artist-in-Residence program; as a result, the artist’s studio and gallery on the first floor is on display for all to see.


Experiencing this Art Deco hotel—on Milwaukee Street, which is lined with trendy bars and restaurants—is akin to stepping back nearly a century. The hotel is a member of the Historic Hotels of America and dates back to the 1930s. Parked out front is a vintage black car that helps shuttle guests around town so you don’t have to brave the cold. You can sip martinis and share dishes like grilled tiger shrimp skewered with Hawaiian pineapple or twin petit filets sautéed in Kahlua cream in Metro Restaurant & Lounge on the hotel’s street level.

With the Valentine’s Day package, guests are treated to handcrafted chocolates, a bottle of Champagne and free overnight valet parking. Some rooms have whirlpool suites.


After an extensive, top-to-bottom renovation, this historic Art Deco hotel reopened in 2005 and now it truly gleams. It’s also a bit off the beaten path, a five-minute drive west of downtown Milwaukee, which makes for a quieter stay. Downstairs is an elegant bar with live jazz on some nights, as well as Envoy, a restaurant serving up gourmet dishes like escargot and truffle frites. Included in the “I Love You—Be Our Valentine” package is a four-course dinner for two that ends on a sweet note with flourless chocolate cake.

Champagne and chocolate-covered strawberries are also folded into the package.