Staypineapple, A Delightful Hotel, South End, Boston — Top Rated (8+) from $97| BestHotel.net

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Staypineapple, A Delightful Hotel, South End Boston Exterior photo

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Key details

About the Hotel

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

Close to Downtown Boston

Great

8.5

9.0

/10

4.1

4.2

Amenities

Staypineapple Boston, A Delightful Hotel, offers a collection of unique amenities including The Naked Experience that features cloud-like European-style individual duvets and cozy robes. Guests can enjoy daily Afternoon Delights with pineapple treats and coffee from 3:30 PM to 6:30 PM in the lobby. A water bar in the lobby provides cold, hot, still, or sparkling water to keep guests refreshed.

Rooms

The hotel provides various room types including the Back Bay King, designed with plush pillow top beds and designer bath products. Each room features high-definition TVs with streaming capability and complimentary high-speed wireless Internet access for all devices. A reusable water bottle is provided in each room and refills are available at the Water Bar.

Location

Situated in the South End, the hotel is just steps away from Back Bay and offers access to historical sites, stylish stores, and exceptional dining options. Guests can reach Arlington Station within a 10-minute walk for direct transport to Fenway Park. Local parks and the Boston Public Garden are also within walking distance, providing outdoor relaxation opportunities.

Dining

At Trophy Room, guests can enjoy a menu inspired by American classics, serving breakfast, dinner, and signature cocktails. The lively atmosphere attracts both locals and hotel guests, making it a popular spot for meals and entertainment. Weekend brunch includes colorful performances alongside familiar favorites, offering a unique dining experience.

Pet Policy

Staypineapple Boston is dog-friendly with its Pineapple Pup Package that includes treats and a collapsible water bowl for furry guests. This package also provides essential supplies like waste bags and a dog bed. Owners can enjoy peace of mind while traveling with pets, enhancing their stay.

Highlights

Location: steps away from Back Bay

Rooms: Back Bay King with plush bedding

Dining: Trophy Room serving American classics

Pet Policy: Pineapple Pup Package available

Must-do experiences

Savor clam chowder at Legal Sea Foods for an iconic treat.
Stroll through the Boston Public Market for local flavors and crafts.
Visit the Isabella Stewart Gardner Museum for art and beautiful gardens.
Catch a Red Sox game at Fenway Park for an unforgettable experience.
Explore the vibrant street art in the South End for colorful snapshots.

View all

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

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Facilities

Staypineapple, A Delightful Hotel, South End offers amenities for your comfortable stay and unforgettable experiences

Facilities: Great

8.4/10Review 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

Dining Onsite

At Staypineapple, A Delightful Hotel, South End, culinary adventures await within the inviting Trophy Room. With a focus on modern American flavors, guests can indulge in a delightful brunch or a cozy dinner in a stylish atmosphere, all just steps from the charm of the South End.

Staypineapple, A Delightful Hotel, South End Boston Restaurant photo

Trophy Room

Modern American

Ambiance

A contemporary yet warm setting, the Trophy Room offers a blend of comfort and sophistication, perfect for relaxing after a day of exploration.

Key Offerings

Brunch delights like avocado toast topped with braised tomatoes and goat cheese, alongside a selection of craft cocktails and wines for dinner.

Reservation

Recommended

Wednesday to Saturday from 4:00 PM to 12:00 AM, and Sunday from 12:00 PM to 8:00 PM.

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

Explore Boston

Explore South End

Boston Common

15 minutes' walk

Historic park offers lush greenery, walking trails, and the perfect spot for picnics and relaxation in the heart of Boston.

Boston Public Garden

15 minutes' walk

Iconic gardens featuring the famous swan boats and vibrant floral displays, ideal for leisurely strolls and enjoying nature.

Faneuil Hall Marketplace

25 minutes' walk

Vibrant shopping and dining hub with historical significance, offering diverse food options and unique shops.

Freedom Trail

16 minutes' walk

National Historic Trail running through Boston's iconic sites, showcasing the city's rich Revolutionary history.

Bike Rentals along the Charles River

15 minutes' walk

Biking along the scenic Charles River Esplanade takes you through beautiful parks; rentals available nearby.

Spa Day at Bliss Spa

10 minutes' drive

Indulge in relaxation with massages and treatments at Bliss Spa, providing a serene escape just a short drive away.

Boston Duck Tours

25 minutes' walk

Unique amphibious vehicle tours highlighting Boston's landmarks, providing a fun and thrilling sightseeing experience.

The Trophy Room

1 minute' walk

Casual eatery known for American comfort food, featuring a lively atmosphere and classic burgers.

Masa

3 minutes' walk

Mexican cuisine blends tradition with modern flair in a vibrant setting; famous for their creative cocktails.

Wink & Nod

2 minutes' walk

Eclectic cocktail bar with a hidden lounge, offering artisanal drinks and a cozy atmosphere perfect for couples.

House of Blues

20 minutes' walk

Live music venue hosting a range of genres; known for its vibrant atmosphere and Southern-inspired menu.

The Wilbur Theater

20 minutes' walk

Historic theater featuring comedy shows and concerts, known for its charming interior and engaging events.

Laugh Boston

10 minutes' drive

Comedy club specializing in stand-up; offers a fun night out with local and renowned comedians performing regularly.

Getting around

City Centre

Boston20 min · 1.0 mi

Airports

Logan (BOS)13 min · 5.3 mi

Worcester Regional (ORH)116 min · 47.7 mi

Train

Boston South Station17 min · 4600 ft

Underground

Back Bay Metro Station5 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 701 verified reviews

8.5/10

Great

84%

Recommend

Breakfast

7.5/10

Cleanliness

8.9/10

Comfort

8.9/10

Facilities

8.4/10

Free Wi-Fi

7.3/10

Location

9.1/10

Paid Wi-Fi

7.6/10

Staff

9.1/10

Value for money

8.1/10

based on 61 reviews

3.5/5

Hudson from Canada

Single

Back Bay King

3 nights in October 2025

Reviewed:December 15, 2025

7/10

prime locationarrival beveragecomfy bedlimited spaceinsufficient spacemini fridge

The location was prime I walked everywhere with ease. A complimentary beverage greeted me upon arrival what a treat. The shower had great water pressure and the bed was super comfy I slept like a log.

The room was a bit small there was limited space to walk around. The bathroom lacked sufficient space for toiletries I found it inconvenient. The absence of a mini fridge in the room was also a downside.

0 Helpful

Elliot from United Kingdom

Single

Back Bay King

3 nights in November 2025

Reviewed:December 09, 2025

7/10

a stay with some minor drawbacks

convenient locationcomfy bedsmall roomsmall bathroom

i found the location to be really convenient for seeing the area. it was nice i could easily walk to different places. the bed was super comfy and i slept very well. i liked there was free coffee in the lobby during the afternoon, it was really useful.

the room felt a little small and there wasn't any closet space. i only had a few hangers on the wall to put my clothes. the bathroom was also quite small. i felt the sink was so tiny that water splashed everywhere when i washed my face.

0 Helpful

FAQs

About Staypineapple, A Delightful Hotel, South End

What is the check-in and check-out policy at Staypineapple, A Delightful Hotel, South End?

Check-in is from 16:00 and check-out is by 12:00.

What are the distances to nearby attractions from Staypineapple, A Delightful Hotel, South End?

Popular attractions include Fenway Park (1 km), the Museum of Fine Arts (2 km), and the Freedom Trail (1 km).

Is there on-site dining available at Staypineapple, A Delightful Hotel, South End?

The hotel's on-site restaurant, Trophy Room, serves an all-American menu for brunch, dinner, and late drinks.

Does Staypineapple, A Delightful Hotel, South End offer free Wi-Fi?

Guests can enjoy complimentary high-speed Wi-Fi throughout the hotel.

What amenities are available in the rooms at Staypineapple, A Delightful Hotel, South End?

Rooms feature air conditioning, a flat-screen TV, coffee maker, and designer bath products.

Which restaurants are located near Staypineapple, A Delightful Hotel, South End?

Nearby dining options include Berkeley Perk Café (0.5 km), Masa (0.5 km), and Grill 23 & Bar (0.5 km).

Are there any recreational activities offered at Staypineapple, A Delightful Hotel, South End?

Bicycles are available for rent, allowing guests to explore the city with ease.

Does Staypineapple, A Delightful Hotel, South End have any notable features?

The hotel features the unique Naked Experience, which includes European-style individual duvets and cozy robes.

What are the hotel highlights of Staypineapple, A Delightful Hotel, South End?

Highlights include a bar/lounge area, 24-hour reception, luggage storage, and vintage fittings throughout.

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