Part of the Gay Provincetown Guide — bars, events & things to do.
Provincetown, Massachusetts
Speakeasy-style gay guesthouse, a P-town landmark for 65+ years.
A gay landmark on Commercial Street for over 65 years, Crew's Quarters is a vintage speakeasy-style guesthouse with 18 rooms and shared community bathrooms inspired by 1920s YMCAs. The property has been queer-owned for six decades — current owner Stuart Jackson restored it in 2020 with period furnishings, artwork honoring queer history, and a guest bar serving cocktails named after gay pulp novels. The vibe is deliberately analog: think pre-app-era boarding house, not boutique hotel. Rooms range from single bunk beds to queen suites with bay views, and communal spaces include a fireplace lobby, front terrace, and first-floor deck overlooking the Pilgrim Monument. Crew's Quarters operates spring through fall with select winter weekends.
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