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The Best Boutique Hotels with Pool in Portland in 2026

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Portland

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McMenamins Kennedy School

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Number of Rooms: 35
Guide Price: Under $200 per Night
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Address: 5736 Northeast 33rd Avenue
Portland
Oregon
97211
Compare it with others in: Affordable Boutique Hotels, Boutique Hotels For Families, Pet Friendly Boutique Hotels, and Boutique Hotels with Pool
It’s hard to find something in the hotel industry that hasn’t been done before, but the novelty of this Northeast Portland school-turned-boutique hotel won’t wear off quickly. Managed by a family-owned Pacific Northwest-based “chain,” the Kennedy School is in the top tier of unique buildings transformed into hotels, pubs, and restaurants. They share the McMenamins name with a slew of transformed schools, chapels, bowling alleys, you name it. The company’s beginnings are relatively unorthodox in the boutique hotel world, starting with pubs and breweries then opening their first hotel in… > Read Our Full Review