Where to stay in Milwaukee
Milwaukee has no gay hotel. The bars are all in Walker's Point, just south of downtown, so the shortest walks are from hotels on the south edge of downtown and in the Third Ward. Downtown proper is a 20- to 30-minute walk or a short rideshare away. The Hop streetcar is free, but it doesn't reach Walker's Point.
Closest to the bars
The Iron Horse Hotel at 500 W Florida St is a boutique hotel in a converted warehouse on the edge of Walker's Point, about 15 minutes' walk from 2nd and National. Kimpton Journeyman Hotel in the Third Ward is a short ride or a 25-minute walk.

Downtown
The Pfister Hotel is the grand 1893 hotel on East Wisconsin Avenue. Saint Kate - The Arts Hotel is an arts-themed hotel next to the Marcus Performing Arts Center. Hotel Metro, Autograph Collection is a small Art Deco hotel, and Hyatt Regency Milwaukee is a large convention hotel near the Wisconsin Center.
Further out
The Knickerbocker on the Lake is on the East Side near the lake. Brumder Mansion Bed & Breakfast is a B&B in a historic mansion on the near west side, and Ambassador Hotel Milwaukee, Trademark Collection by Wyndham is an Art Deco hotel near Marquette University. Potawatomi Casino & Hotel is in the Menomonee Valley.

Tips
Book early for PrideFest in early June, when Summerfest-season prices also apply. If you'll spend your nights on 2nd Street, stay in the Third Ward or Walker's Point and walk.