Staypineapple, A Delightful Hotel, South End

Non-Discrimination Policy

Staypineapple, A Delightful Hotel, South End

Name: Staypineapple, A Delightful Hotel, South End
Brand: misterb&b
SKU: b150773-hotel
Rating: 4.79 (14 reviews)

Hotel•Powered by a trusted agency partner

26 Chandler Street, Boston, MA, United StatesGay District•Map

Exceptional4.8(Booked 15 times)

Out of 100

Gay Welcoming Score: The Community's Verdict

Out of 100

Based on LGBTQ+ travelers' ratings, this score reflects the overall LGBTQ+ friendliness of this hotel.

14 LGBTQ+ travelers have rated this property. After your stay, you'll be invited to rate it too.See all reviews

BrianStayed: March 2026

“We chose the hotel for the sofa. But the real stars are the kind staff. I became ill during our stay. Cynthia, Issac, Carlos, and Jonathan went out of their way to make me comfortable. Their kindness was beyond standard hospitality. It was delightful. PS, I recovered and enjoyed Boston.”

Choose a room that gets you

Sleeps 2

Unveiling the Hotel

Located in Boston's historic South End, this European-style boutique hotel offers modern guest rooms with free WiFi. Staypineapple, South End is within walking distance to many popular restaurants and attractions.

Every room at The Staypineapple, South End features a flat-screen TV and iPod docking station. The private bathroom includes a walk-in marble shower. A work desk and telephone with access to the 24-hour front desk are provided for guest convenience.

Only steps from the completely nonsmoking property are some of the city's most famous sites. The scenic Back Bay area, as well as the unique shops and gourmet restaurants of Newbury Street are within 10 minutes' walk.

Little Luxuries

Pets allowed

Restaurant

Bar

Elevator

Wi-Fi

Air conditioning

Heating

Appliances

Wi-Fi

Air conditioning

Heating

Access

Elevator

Welcome

Pets allowed

Hotel facilities

Restaurant

Bar

Why Book Proud with misterb&b?

Travel with purpose. Support the LGBTQ+ community with every stay.

Your discretion is guaranteed

Your invoice and bank statement only show the accommodation's name, never misterb&b.On your statement:Staypineapple, A Delightful Hotel, South End

Every stay gives back to the community

This booking will contribute to our Mister for Good program, helping LGBTQ+ NGOs around the world.

Built by and for the LGBTQ+ community

We're an LGBTQ+-owned platform. Your support directly funds jobs and livelihoods for our LGBTQ+ team.

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Where It's All Happening

26 Chandler Street, Boston, MA, United StatesExact location disclosed after booking only.

LGBTQ+ Safety Score: Boston

4.79out of 5Very safeRated by 14 local misterb&b members

Your Queer Map: Nearby Gay Hotspots

Full gay city guide for Boston »

Gay Bars & ClubsClub Café Lounge & Vidéo Bar209 Colombus Avenue

208 m4-minute walk

Gay Saunas & CruisingHot Mess Sundays275 Tremont Street

568 m12-minute walk

Gay Bars & ClubsDani’s Queer Bar909 Boylston St

1.1 km24-minute walk

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1448 active members around the city this month, ready to show you their favorite spots.

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House Rules & Conditions

Check-infrom 4pm

Checkoutto 12pm

Deposit

A partner agency manages this listing. Please review the description, pricing, and conditions carefully, as they may require the security deposit to be collected directly from you.

Type of accommodationAgency Partner

Agency Partner

Please find here the specific Terms & Conditions applicable to Agency Partner listings.

How does this work on misterb&b?

This property is listed through a partner agency with which misterb&b has an agreement. The agency requires all of its accommodations to adhere to a non-discrimination charter—precisely why we chose this partner. The property itself has no direct relationship with misterb&b.

Cancellation Policy

Terms of Services & Privacy Policy apply to this transaction.

The need-to-knows

Good to know

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.

Age restriction

The minimum age for check-in is 18

Accepted payment methods

ReviewsExceptional4.79(14)

Member reviews:4.25(4)•Automatic reviews:5(10)-

Reviews come from verified guests, are sorted chronologically and not subjected to prior monitoring.

Cleanliness5.0

Location4.7

Accurate description4.7

Check-in5.0

Value for money3.7

Our Community Has Spoken:

BrianStayed in March 2026

Reviewed on Apr. 08, 2026

We chose the hotel for the sofa. But the real stars are the kind staff. I became ill during our stay. Cynthia, Issac, Carlos, and Jonathan went out of their way to make me comfortable. Their kindness was beyond standard hospitality. It was delightful. PS, I recovered and enjoyed Boston.

misterb&b

Automatic 5-star review on Feb. 05, 2026