75 photos

Staypineapple, A Delightful Hotel, South End Boston Exterior photo

Exclusive direct rates

up to 10% less

than on Booking.com

Key details

About the Hotel

26 Chandler St, Boston, 02116

Great

8.5

9.0

/10

4.2

4.3

“The South End is a beautiful area perfect for leisurely strolls.”view full review

Located merely 1.3 km from the historical Freedom Trail, the 4-star boutique-style Staypineapple, A Delightful Hotel, South End Boston is about a 5-minute walk from the graceful Arlington Street Church. A lounge bar as well as a shared lounge and various recreational opportunities can be enjoyed at the comfortable hotel, boasting the setting within reach of the Trinity Church.

Location

The hotel has a prime location within 25 minutes' walk of the public Christopher Columbus Waterfront Park, while shopping venues like the historic indoor-outdoor shopping center "Faneuil Hall Marketplace" are around 30 minutes' walk away. Boston Common Public Park is within a few blocks of the Staypineapple, and Logan airport is 5 km away.

Visit The Lagoon, 850 metres from this accommodation, and feel complete harmony with the nature of United States. Options for cultural tourism include the Museum of Fine Arts, situated 2.1 km away.

The nearest tube station to Staypineapple, A Delightful Hotel, South End is Back Bay, 400 metres away.

Rooms

This Boston hotel has 56 rooms appointed with an iPod dock and a 50-inch flat-screen TV, as well as self-catering options such as coffee and tea making equipment. An iron with ironing board are featured for guests' comfort.

Eat & Drink

Grill 23 & Bar offers American dishes and is situated steps away from the Staypineapple Boston.

Select your room type

Staypineapple, A Delightful Hotel, South End offers a variety of rooms including double rooms, family rooms, and suites with breakfast, free cancelations, and special deals

Back Bay King

2 persons

18 sq. feet

1 King-size bed

Coffee machine

Shower

room details

South End Corner King

2 persons

18 sq. feet

1 King-size bed

Coffee machine

Shower

room details

Price and Room Availability Calendar

Check availability and prices for your dates now!

September 2026 - September 2027

Sun

Mon

Tue

Wed

Thu

Fri

Sat

September 2026

October 2026

November 2026

December 2026

January 2027

February 2027

March 2027

April 2027

May 2027

June 2027

July 2027

August 2027

Choose dates to see prices

Check-in/ Check-out

Facilities

Amenities designed for comfort – Perfect for layovers & transit travelers

Tasty Eats at Trophy Room

“I had to mention the food at The Trophy Room bar & restaurant! The pineapple teriyaki wings were absolutely delicious and a must-have. It made dining in the hotel a good experience, and paired with their excellent draft beer, it was the perfect way to unwind after a day of exploring.” read full review

Cozy and Clever Design

“My Beautiful King Room was thoughtfully designed with clever storage solutions. I appreciated the large drawer underneath the bed where I could stash my bigger suitcase. It was cozy and efficient, making the most out of the space provided!” read full review

Heavenly Sleep Experience

“The bedding in my room was incredibly comfortable! I loved the European-style duvet, made for a snug and restful night's sleep after a long day. It was exactly what I needed for a good stay!” read full review

Fun Streaming Options

“I was actually surprised to find that I could easily connect my device to stream my favorite shows right on the room's TV. This little feature added a great touch to my downtime in the cozy room - it was like home!” read full review

Facilities: Great

8.3/10Review score