Staypineapple, A Delightful Hotel, South End, Boston - Reviews, Room Options & Prices 2025

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About the Hotel

26 Chandler St, Boston, Massachusetts, United States, 02116

Great

8.5

9.0

/10

4.2

“The location was perfect, within walking distance of top attractions!”view full review

Staypineapple, A Delightful Hotel, South End offers a modern 4-star experience in Downtown Boston's historic South End district, steps from Back Bay. This award-winning hotel features The Naked Experience with European-style duvets and provides complimentary bikes, afternoon coffee service, and a 24-hour front desk.

Luxurious Room Comforts

Each thoughtfully designed room at Staypineapple features plush pillow-top beds with European-style double duvets and designer bath products. The South End Corner King rooms offer added quietness with dual windows and partial city views, while all accommodations include flat-screen TVs with streaming capabilities.

Dynamic Dining Options

The Trophy Room, a window-lined venue, serves American classics and creative cocktails including the signature Trophy Wife with passion fruit and elderflower vodka. Berkeley Perk Café offers breakfast tacos and omelets, while the lobby provides afternoon pineapple treats.

City Adventure Amenities

Staypineapple Boston provides beach cruiser bikes for city exploration. The property features a Quick Bites & Bevvies cooler, available 24/7, and hosts the SoWa Open Market from summer through December with artist and vintage wares.

Central Boston Location

Located a 10-minute walk from Arlington Station, the hotel provides easy access to Fenway Park and Freedom Trail sites. The John Hancock Tower stands 0.5 miles away, while Boston Public Garden is 1 miles from the property.

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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

South End Corner King

2 persons

195 sq. feet

1 King-size bed

Shower

Coffee machine

room details

Back Bay King

2 persons

195 sq. feet

1 King-size bed

Shower

Coffee machine

room details

Price and Room Availability Calendar

Check availability and prices for your dates now!

Facilities

Experience a variety of amenities at the boutique hotel, crafted to ensure your comfort and unforgettable moments

Quirky & Cute

“I absolutely loved the quirky pineapple-themed decor throughout the room. From the fluffy robes to the fun pillows, everything had a good twist. The room, while cozy, was designed in a way, made great use of space, making me feel at home during my stay.” view full review

Super Comfortable Bed

“The bed was incredibly comfortable! After a long day of exploring, sinking into that cozy mattress with my own personal duvet was like a dream come true. It was the perfect oasis to recharge for more adventures.” view full review

Charming Bath Details

“While the bathroom was on the smaller side, it was beautifully appointed with charming details. The shower provided adequate water pressure, and I appreciated the cleanliness and modern touches, making it a pleasant space to freshen up.” view full review

Lively Bar Scene

“I enjoyed the lively atmosphere at the Trophy Room bar in the lobby. The complimentary drink upon arrival was a nice touch, and the bar had a great vibe where I relaxed after a busy day. It was the perfect spot to unwind with a drink.” view full review

Facilities: Great

8.2/10Review score

General

No smoking on site
Wi-Fi
24-hour reception
Pets allowed
Luggage storage
Lift
Smoke detectors
Fire extinguishers
Key card access

Services

Pet amenities available
Housekeeping

Dining

Restaurant
Bar/ Lounge area

Room features

Air conditioning
Heating
Tea and coffee facilities
Ironing facilities

Media

Flat-screen TV

Staypineapple, A Delightful Hotel, South End Location

26 Chandler St, Boston, Massachusetts, United States, 02116

Map view

26 Chandler St, Boston, Massachusetts, United States, 02116

City landmarks

Stadium

Fenway Park

1.4 mi

Landmark

Boston Common

3900 ft

Market

Faneuil Hall Marketplace

1.4 mi

Park

Boston Public Garden

4100 ft

Landmark

Freedom Trail

4200 ft

Museum

Museum of Fine Arts

1.3 mi

Aquarium

New England Aquarium

1.4 mi

Museum

Museum of Science

1.4 mi

Museum

Boston Tea Party Ships & Museum

1.3 mi

Library

Boston Public Library

2900 ft

Parking area

Skywalk Observatory

3700 ft

Square

Copley Square

2600 ft

Landmark

North End

1.5 mi

Spa Centre

Newbury Street

3900 ft

Landmark

Freedom Trail walk

1.6 mi

Church

Trinity Church

2200 ft

Cemetery

Granary Burying Ground

5100 ft

Landmark

Boston Children's Museum

1.5 mi

Tower

John Hancock Tower

2100 ft

Monument

New England Holocaust Memorial

1.3 mi

Monument

Bunker Hill Monument

2.1 mi

Museum

The Paul Revere House

1.4 mi

Landmark

Beacon Hill

1.2 mi

Museum

Isabella Stewart Gardner Museum

1.6 mi

Landmark

Quincy Market

1.3 mi

Museum

The Institute of Contemporary Art

1.5 mi

Public Building

Old State House

1.2 mi

Museum

USS Constitution Museum

2.0 mi

Theatre

Boston Symphony Hall

5100 ft

Landmark

Back Bay

3100 ft

Nearby

Boston Public Garden Facing the Arlington Street Entrance

George Washington Statue

1400 ft

Arlington Street Boston Public Garden

Ether Monument

1400 ft

Church

Arlington Street Church

1400 ft

Restaurants

The Trophy Room

0 ft

26 Chandler Street

Wink & Nod

500 ft

3 Appleton St

Masa

600 ft

439 Tremont Street

Cosmica

600 ft

40 Berkeley St Located in the Revolution Hotel

Bootleg Special

700 ft

400 Tremont St

Club Cafe

1000 ft

209 Columbus Ave

Flour Bakery & Cafe

1300 ft

131 Clarendon St

Barcelona Wine Bar

1100 ft

525 Tremont Street

Citrus & Salt

900 ft

142 Berkeley St

The Beehive

1300 ft

541 Tremont St

Getting around

City Centre

Boston20 min · 1.0 mi

Airports

Logan International Airport (BOS)13 min · 5.3 mi

Worcester Regional Airport (ORH)116 min · 47.7 mi

Train

Boston South Station17 min · 4600 ft

Underground

Back Bay5 min · 1400 ft

Bus

Bus stop2 min · 400 ft

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Property information and rules

Check-in

from 16:00-23:59

Check-out

until 12 pm

Guest Parking

No parking available.

Internet

Wireless internet is available in for free.

Children & extra beds

There are no cots provided in a room.

Pets

Pets are allowed on request.

Year renovated:

2011

Number of floors:

Number of rooms:

Former name

Chandler Inn Hotel

Reviews and Ratings

Feedback about Staypineapple, A Delightful Hotel, South End from previous guests about their experience.

Review score

Based on 641 verified reviews

8.6/10

Great

86%

Recommend

Breakfast

7.5/10

Cleanliness

8.7/10

Comfort

8.7/10

Facilities

8.2/10

Free Wi-Fi

8.1/10

Location

8.9/10

Paid Wi-Fi

7.5/10

Staff

9.0/10

Value for money

7.9/10

based on 61 reviews

3.5/5

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