Staypineapple, A Delightful Hotel, South End | City stay in Boston | Book Now

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Key details

About the Hotel

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

Rooms & Amenities

Staypineapple Boston offers rooms with plush pillow-top beds, European-style double duvets, and high-speed Wi-Fi. Each room includes a Keurig coffee maker, flat-screen TV with streaming, and marble-tiled bathrooms with walk-in showers. The South End Corner King provides extra natural light and partial city views.

Dining & Drinks

The Trophy Room serves American classics, including the Chandler Street Burger and signature cocktails like the Trophy Wife (vodka with passion fruit and elderflower). The adjacent Berkeley Perk Café offers breakfast tacos and omelets. A self-service coffee station and pineapple treats are available in the lobby.

Leisure & Activities

Guests can borrow yellow beach cruisers to explore Boston. The Trophy Room hosts trivia nights and weekend breakfast with live performances. Afternoon coffee and pineapple treats are served daily from 3:30 PM to 6:30 PM.

Location & Access

The hotel is on the border of Back Bay and South End, 400 m from Back Bay Station and 550 m from Arlington Station (Green Line). Fenway Park is a 10-minute train ride away. Nearby attractions include the Freedom Trail (1 km) and Copley Square (0.5 km).

Guest Services

Services include 24-hour front desk assistance, free Wi-Fi, and reusable water bottles with refill stations. Dog-friendly rooms come with a bed, treats, and a collapsible bowl. The Everything Button connects guests to additional requests like extra coffee or dining recommendations.

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Choose the Room

From cosy doubles to spacious family suites – all with flexible options, breakfast, and exclusive deals.

South End Corner King

Max:

2 persons

195 sq. feet

Bed options:

1 King-size bed

Shower

room details

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Back Bay King

Max:

2 persons

195 sq. feet

Bed options:

1 King-size bed

Shower

room details

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Check Dates & Room Rates

See what's available for your travel dates

Getting around

All Transportation Options at a Glance

City Centre

Boston 1.0 mi

Airports

Logan (BOS) 5.3 mi

Worcester Regional (ORH) 47.7 mi

Train

Boston South Station4600 ft

Underground

Back Bay1400 ft

Bus

Bus stop400 ft

Amenities

Thoughtfully designed amenities for a comfortable & memorable stay

Free Wi-Fi

Parking

Luggage storage

24-hour services

24-hour reception

General

No smoking on site
Free 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

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

Guest Ratings & Reviews

Real Guest Experiences & Ratings

3.5/5 based on 61 reviews

#81 of 89 hotels in Boston based on Tripadvisor

Herbert

United Kingdom, May 2024

7.4/10

I had a great stay at the hotel! The rooms were clean and perfect for a solo traveler like me. The service was top-notch, although there were some minor inconveniences with noise outside. The location was excellent for exploring the city on foot. The dining was good, especially with the attached restaurant offering breakfast options. Overall, a lovely place to stay with a few small drawbacks.

Rooms

8.0

The rooms were comfortable, clean, and the perfect size for a solo traveler. They were quiet, but there was some city noise that required using a white noise app to sleep.

Service

7.0

The service was top-notch, with very kind and helpful staff. However, there were some limitations on amenities like bottled water and coffee availability.

Location

9.0

The hotel's location was central for everything I wanted to do, making it easy to see a show, walk the Freedom Trail, and enjoy unique local cuisine. It was a bit far from some specific points like the convention center, but overall, well-placed for exploring the city on foot or using public transportation.

Dining

7.0

The dining experience was good, especially with the attached restaurant offering breakfast options. However, there were a few limitations, and the crisps were just okay.

Facilities

6.0

The facilities were decent, but there were some minor inconveniences. Overall, they met my needs adequately.

Great location

Noise outside

Gary

United States, April 2024

8.0/10

The hotel had basic yet clean rooms, but the absence of a chair made it inconvenient. The service was exceptional, with understanding staff who went above and beyond to assist. The location was excellent for exploring Boston's main attractions. The dining options were good, and the facilities were up to standard.

Rooms

7.0

The rooms were basic and clean, as expected for a three-star hotel. The absence of a chair made it difficult for practical use.

Service

9.0

The staff provided outstanding service, being kind, friendly, and very accommodating, including loaning an umbrella and offering helpful tips.

Location

8.0

The hotel's location on the edge of South Boston and South End was quiet, convenient for accessing central areas, and part of a charming residential neighborhood.

Dining

8.0

The dining options, including those in the adjacent Trophy Restaurant, were satisfying. The availability of big salads was a plus.

Facilities

8.0

The facilities met expectations and provided what was needed for a comfortable stay.

Andrew

United Kingdom, January 2024

7.6/10

The hotel rooms were cozy and had all the amenities we needed, although they did smell like cigarette smoke at times and there were constant noises throughout the night. The service was friendly, and I appreciated that they let me keep my luggage before and after check-in/check-out. The location was central for everything I wanted to do, but it is in a nice but somewhat noisy residential area. The dining options were not super active, but I could enjoy good coffee on weekdays without extra charges. The facilities were adequate, and the price was reasonable overall.

Rooms

7.0

The rooms were cozy and had all the amenities we needed. They smelled of smoke occasionally and there were constant noises throughout the night.

Service

8.0

The service was friendly, and I could keep my luggage there before and after check-in and check-out.

Location

8.0

The location was quite good, central for everything I wanted to do, albeit in a somewhat noisy residential area.

Dining

7.0

The dining experience offered good coffee on weekdays without extra fees.

Facilities

8.0

The facilities were small but adequate and the price was reasonable.

Hugh

United Kingdom, November 2023

8.6/10

I absolutely loved my stay at this hotel! The cleverly designed rooms were compact but perfect for our needs, especially since we spent most of our time exploring outside. The bathroom utilized the small space brilliantly, although a lack of a work desk was a downside. The hotel's location was ideal for exploring Boston, with easy access to public transportation and plenty of nearby attractions and dining options.

Rooms

8.0

The rooms had a wide windowsill almost within reach that I used, compact yet functional, with a cleverly designed bathroom maximizing the space. The only drawback was the absence of a work desk.

Service

8.0

The service was great with friendly staff welcoming us with a smile. The only slight negative was the slightly bizarre check-in experience with expressionless staff.

Location

9.0

The location was perfect for exploring Boston, walkable to many attractions, near public transportation, and surrounded by restaurants and bars. It was a quiet and trendy area in a safe district.

Dining

9.0

The dining options were amazing both in the hotel and nearby establishments, offering top-notch quality that rivaled five-star hotels. The only minor complaint was regarding nibbles availability.

Facilities

9.0

The facilities were modern and clean, offering everything needed for a comfortable stay.

Ryan

United Kingdom, July 2023

7.4/10

The hotel is in a great area with lots of restaurants and very close to all tourist attractions. The rooms felt a bit sticky, and there was some city noise while trying to sleep. The service was accommodating but a bit slow at times. The hotel's location is fantastic for exploring Boston, and the dining experience required heading out of the hotel. Overall, a convenient spot with a few minor drawbacks.

Rooms

7.0

The rooms felt sticky and there was some city noise while trying to sleep.

Service

7.0

The service was accommodating but a bit slow at times.

Location

9.0

The hotel is in a great area with lots of restaurants and very close to all tourist attractions.

Dining

6.0

The dining experience required heading out of the hotel.

Facilities

8.0

The hotel had pet amenities available.

Thomas

United States, June 2023

8.8/10

My stay at the hotel was fantastic! The rooms were comfortable and updated, with beautiful hardwood floors and a great walk-in shower. The location was perfect, right in the heart of the action in South Boston. The service was top-notch, with kind and attentive staff. The dining options were good, and the facilities were well-maintained. Overall, a great choice for a stay in Boston!

Rooms

9.0

I loved the rooms, they were so comfortable and nicely styled.

Service

9.0

The staff was incredibly kind and attentive, making my stay very enjoyable.

Location

10.0

The hotel's location in South Boston was perfect for me, close to everything I needed.

Dining

8.0

The dining options were good, either at the onsite restaurant or nearby local establishments.

Facilities

8.0

The facilities were well-maintained and added to the overall comfort of my stay.

Tom

United States, June 2023

8.2/10

I had a cozy room with all the amenities I needed in a small but adequate space at this hotel with an excellent city location. While fairly clean, there was a strange smell present. The service was top-notch, with very friendly and helpful staff at the desk, making my stay very pleasant. The location was central, perfect for exploring the city easily. The dining experience was mediocre, but the presence of fresh local fish was a nice touch.

Rooms

8.0

My room was cozy and had all the amenities I needed in a small but adequate space. There was a strange smell, but overall it was fairly clean.

Service

9.0

The staff was very friendly and helpful, making my stay enjoyable.

Location

10.0

The hotel's location was excellent for everything I wanted to do in the city, within walking distance of most transport and tourist sites.

Dining

6.0

The dining was mediocre overall, although the presence of fresh local fish was a nice touch.

Facilities

8.0

The hotel had all the necessary facilities for a comfortable stay.

Great location

Strange smell

Richard

United Kingdom, June 2023

8.4/10

The hotel is situated in a lovely part of the city, full of great restaurants, and just a short walk to downtown. The rooms are efficiently designed, but the AC/heater could use some cleaning and the blinds are not the best quality. However, they were immaculately clean and well-presented. The service is wonderfully friendly and helpful, though a slight issue with the slamming door puzzled me. The location is fantastic, with a quiet residential neighborhood and attractive surroundings. Dining options are available in the adjoining Trophy Restaurant, including a coffee maker in the room. Overall, a great choice with a few minor room issues.

Rooms

7.0

The rooms were functional, a bit small, and could use some improvements with the AC/heater and blinds.

Service

9.0

The service provided was fabulous, with helpful staff willing to accommodate changes in reservations.

Location

10.0

The location is fantastic in a lovely part of the city, close to great restaurants and just a short walk to downtown.

Dining

8.0

Dining options are available in the adjoining Trophy Restaurant, with a coffee maker in the room for convenience.