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 of America, 02116

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 0.8 miles from the property.

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Select your room type

The hotel offers a variety of rooms including double rooms, family rooms, and suites with breakfast, free cancelations, and special deals

Corner King Room

Max:

2 persons

18 m²

Bed options:

1 King Size Bed

Shower

Coffee machine

room details

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Deluxe King Room

Max:

2 persons

18 m²

Bed options:

1 King Size Bed

Shower

Coffee machine

room details

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Price and Room Availability Calendar

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Getting around

A guide to all available transportation options

City Center

Boston 1.0 mi

Airports

Logan (BOS) 5.3 mi

Worcester Regional (ORH) 47.7 mi

Train

Boston South Station4600 ft

Metro stations

Back Bay1400 ft

Bus

Bus stop400 ft

Facilities

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

Wi-Fi

Parking

Baggage storage

24-hour services

24-hour reception

General

No smoking on site
Wi-Fi
No parking
24-hour reception
Pets allowed
Baggage storage
Elevator
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

Location

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

Map view

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

City landmarks

Stadiums

Fenway Park

1.4 mi

139 Tremont St

Boston Common

3900 ft

Market

Faneuil Hall Marketplace

1.4 mi

Parks

Boston Public Garden

4100 ft

Boston

Freedom Trail

4200 ft

Museums

Museum of Fine Arts

1.3 mi

Aquarium

New England Aquarium

1.4 mi

Museums

Museum of Science

1.4 mi

Museums

Boston Tea Party Ships & Museum

1.3 mi

Libraries

Boston Public Library

2900 ft

Parking area

Skywalk Observatory

3700 ft

Square

Copley Square

2600 ft

Boston

North End

1.5 mi

Spa Center

Newbury Street

3900 ft

32 Mallard Cove Way

Freedom Trail walk

1.6 mi

Church

Trinity Church

2200 ft

Cemetery

Granary Burying Ground

5100 ft

308 Congress St

Boston Children's Museum

1.5 mi

Tower

John Hancock Tower

2100 ft

Monuments and Landmarks

New England Holocaust Memorial

1.3 mi

Monuments and Landmarks

Bunker Hill Monument

2.1 mi

Museums

The Paul Revere House

1.4 mi

Between Beacon St and Cambridge St Beacon Hill

Beacon Hill

1.2 mi

Museums

Isabella Stewart Gardner Museum

1.6 mi

4 S Market St

Quincy Market

1.3 mi

Museums

The Institute of Contemporary Art

1.5 mi

Public Building

Old State House

1.2 mi

Museums

USS Constitution Museum

2.0 mi

Broadway Theatre

Boston Symphony Hall

5100 ft

Boston

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

Reviews and Ratings

Feedback from previous guests about their experience.

84%

enjoyed the hotel and would happily stay again

8.4/10

Great

Rooms

6.4

Location

9.2

Service

8.4

Dining

7.4

3.5/5 based on 61 reviews

#81 of 89 hotels in Boston based on Tripadvisor

Taylor

United Kingdom, March 2025

7.4/10

I had a lovely stay at Staypineapple in Boston's South End. The bed was super comfy, and the cleanliness of the hotel made my experience even better. However, the room was smaller than I expected, and I encountered a few minor issues with the bathroom plumbing. Overall, it was a good experience, and I appreciate the unique character of the place.

Rooms

7.0

The room was adorable and had everything I needed, but it was definitely small, with limited space for my suitcase.

Service

10.0

The staff were incredibly friendly and accommodating, really going out of their way to help me, especially with the morning coffee.

Location

9.0

The hotel's location was ideal for exploring Boston, conveniently close to the metro and within walking distance to many attractions.

Dining

9.0

I enjoyed breakfast at the onsite restaurant, and it tasted as good as any five-star dining experience I've had.

Facilities

8.0

I appreciated the unique decor throughout the hotel and the eco-friendly initiatives like the refillable water stations.

Nathaniel

United Kingdom, March 2025

5.0/10

My stay at Staypineapple was a mix of good experiences and some challenges. The staff were incredibly friendly and made me feel welcome, while the rooms were clean and had a quirky pineapple decor that I loved. However, I faced issues with noise from a barking dog in the neighboring room which disturbed my sleep. Overall, I appreciated the hotel’s unique charm, but the noise issue left me feeling a bit less relaxed than I had hoped for.

Rooms

7.0

The room was cute and clean, but quite small. I struggled with space while trying to open my suitcase. The decor, however, was charming and reflected the pineapple theme well.

Service

9.0

The staff were friendly and accommodating. I felt genuinely welcomed during my stay, which added to the overall experience.

Location

10.0

The hotel's location is fantastic. it’s just a short walk to many restaurants and attractions, making it easy to explore Boston.

Dining

7.0

I enjoyed the onsite bar, but I found the tables to be a bit small. it had a nice atmosphere, though the cost of amenities was a surprise.

Facilities

8.0

The hotel was clean and had thoughtful amenities, though I felt the area around the bar could use a more enclosed vibe. I appreciated the pet-friendly policies.

Norman

United Kingdom, February 2025

5.8/10

I enjoyed my stay at Staypineapple in the South End, appreciating the friendly staff and quirky pineapple theme. though the room felt a bit cramped. Cleaning wasn't daily, which can make it uncomfortable after a while. Overall, the location was excellent for exploring Boston, but I wished for more space and better housekeeping.

Rooms

6.0

The room was nicely decorated but definitely on the small side. the configuration made it difficult to find space for luggage. I appreciated the comfortable bed, though the lack of a mini-fridge was a bummer.

Service

7.0

The staff were very friendly and accommodating, making check-in a warm experience. However, I felt that housekeeping could have been more consistent.

Location

8.0

The location in the South End was convenient for exploring local restaurants and bars. walking to popular areas like Newbury Street was a breeze.

Dining

7.0

I enjoyed breakfast at the Trophy Room, which had good options. it's nice that they offer complimentary wine during check-in!

Facilities

6.0

The hotel was clean and maintained. but I found the heating a bit inconsistent, and it would have been nice if they had daily room cleaning.

Henry

United Kingdom, February 2025

6.4/10

Staypineapple offered a cozy, charming experience in the heart of Boston's South End, complete with friendly staff and a quirky pineapple theme. However, I found the rooms to be quite cramped, making it a bit challenging to move around, especially with luggage. The bathroom was exceptionally small, and I did feel some allergy issues during my stay. Overall, it has potential but could use some improvements in room size and amenities.

Rooms

6.0

The room was beautifully decorated but cramped, making it difficult to manage my luggage. The bathroom was particularly small, barely allowing me to navigate comfortably.

Service

8.0

The staff were exceptionally friendly and helpful, providing assistance and local tips whenever needed. They made my stay enjoyable despite the room size.

Location

9.0

Located conveniently near the Back Bay transit station and popular attractions, it made exploring Boston on foot very easy. The neighborhood itself was lovely for strolls.

Dining

7.0

Dining options were limited, but the connected Trophy Restaurant offered good vibes and friendly service, making it a nice place to unwind after a long day.

Facilities

6.0

While the hotel was clean and well-maintained, the $15 amenity fee felt unnecessary given the limited amenities provided, such as bottled water only upon arrival.

Hudson

United Kingdom, November 2024

5.6/10

I had a good stay at Staypineapple in Boston, though the room was quite small, which might not suit everyone. The location was fantastic, making it easy for me to explore the city. I loved the quirky decor and the friendly staff, but I did feel the need for a bit more space and amenities for the price I paid.

Rooms

6.0

The room was tiny and lacked a closet or desk, but it was clean and had a cozy ambiance. I enjoyed the bed's comfort, though I really wished for a hook on the bathroom door.

Service

8.0

The staff was generally friendly and helpful, making my stay pleasant. I appreciated their willingness to give advice about the city.

Location

10.0

The hotel's location is perfect for visiting Boston's main attractions. I was able to walk to most of the popular spots and eateries, which was a huge plus.

Dining

7.0

I enjoyed some complimentary coffee in the room and the snacks were nice touches, although the food options could be improved as I didn't dine extensively at the onsite restaurant.

Facilities

6.0

The hotel offered unique amenities like bicycles to explore the city and refillable water stations, which I found to be eco-friendly. However, the fitness center was quite limited with only two exercise bikes.