Dylon and his best friend had one dream: to see Paris Hilton DJ live in NYC. They dropped everything to make it happen — and with one spontaneous decision, they booked a stay at Staypineapple New York.
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Jennifer and her family’s cross-country journey led to unforgettable memories at Staypineapple Chicago — so special, they came back for more.
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Two moms and their daughters shared a special first road trip from Vancouver, staying at The Maxwell Hotel and enjoying a Lauren Daigle concert in Seattle.
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Austin and his partner had a festive holiday experience at Staypineapple Chicago, watching the Thanksgiving Parade before exploring the nearby Christkindlmarket.
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Tell us about your incredible Staypineapple experience!
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Staypineapple guests Jane and Shane Harrington and daughter Amelia share their experiences at Watertown Hotel and their adventures at Staypineapple HQ.
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A long-distance relationship, pineapple onesies and a surprise proposal made for a memorable anniversary celebration at Staypineapple Chicago.
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