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Staypineapple, A Delightful Hotel, South End

8.5/101638 reviewsBoston

Charming European-Style Boutique Hotel in Boston's South End Modern Amenities: Each room at Staypineapple, South End boasts a flat-screen TV, iPod docking station, and a luxurious walk-in marble shower in the private bathroom. Convenient Services: Guests can enjoy free WiFi, a work desk, and a direct line to the 24-hour front desk for any needs that may arise during their stay. Prime Location: Situated in the historic South End, the hotel is just a short stroll away from renowned restaurants and attractions, including the vibrant Back Bay area and upscale shops on Newbury Street. Ready to experience the perfect blend of comfort and sophistication? Book your stay at Staypineapple, South End now!

What this place offers

  • WiFi available
  • Free WiFi
  • Non-smoking rooms
  • Air conditioning
  • 24-hour front desk
  • Restaurant

Policies & house rules

  • Check-in from 16:00
  • Check-out until 12:00
  • Children welcome
  • Pets allowed
  • No parking

Please note, guest must be a minimum of 18 years of age to check in. Please note that, Reservations for 10 rooms or more need to be contracted as a Group with the hotel directly.Guests are required to show a photo ID and credit card upon check-in. Please note that all Special Requests are subject to availability and additional charges may apply. A deposit may be required at the property.

Available rooms

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1638 reviews

Guests liked

  • Friendly staff
  • Clean rooms
  • Great location
  • Fun amenities

Guests mentioned

  • Noise issues
  • Small room sizes
  • Limited storage space

  • Dave

    GB · couple · Oct 2026

    8/10

  • Viktoriia

    NZ · couple · Oct 2026

    6/10

    Fine for a very short stay, but not for an extended.

    Comfortable beds: We prefer firm mattresses and really appreciated having individual blankets. We use the Scandinavian sleep method at home, too, so it was great not to have to share a duvet. The king-size bed was very comfortable, and we appreciated the choice of small and medium-sized pillows rather than oversized ones. The location was great, in a nice neighbourhood and easily accessible. We were pleased to learn about their support for dog adoption and overall it’s a lovely pet-friendly place.

    The rooms are very small and quite tired. There’s no clothes storage, a refrigerator or electric kettle, and the bathroom is also small. My partner and I both hurt ourselves while getting ready for a shower. We’re both quite small people, but moving between the tiny sink, shower glass wall and toilet was difficult.

  • Toby

    US · couple · Oct 2026

    9/10

    Location and comfort

    Smaller bathroom, price

  • KARA

    US · couple · Oct 2026

    5/10

    I’m glad I got the chance to check it out, but I would not be staying there again

    It was quirky and cute and the bed was really comfortable

    It was just so small and overpriced in the bathroom was ridiculously tiny

  • Jordanne

    US · couple · Oct 2026

    10/10

    If hospitality was a fruit it would be a Pineapple

    The employees at the hotels, especially Mitchel who is the night desk manager, were incredibly kind and helpful, often going above and beyond to make sure I had what I needed.

    There was nothing not to like really, besides the fact that there is a shortish window to grab the pineapple sugar cookies in the afternoon and I missed the window my second day.

Location

26 Chandler St · Boston