Staypineapple, A Delightful Hotel, South End Boston Exterior photoStaypineapple, A Delightful Hotel, South End Boston Exterior photoStaypineapple, A Delightful Hotel, South End Boston Exterior photo

Staypineapple, A Delightful Hotel, South End, Boston

Book and save
up to 10%
compared to Booking.com
Check rooms and rates
From$97 /night
Check-in
30Jul
Check-out
31Jul
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

26 Chandler St, Boston, 02116
Great
8.5
9.0
/10
4.1
4.3
/5

4-star hotel in Boston's South End with The Naked Experience

Amenities

Staypineapple, A Delightful Hotel offers The Naked Experience, which includes cloud-like European-style individual duvets and cozy robes. Guests can relax with signature pineapple treats alongside locally sourced refreshments. The hotel also has a Water Bar for refilling water bottles with cold, hot, still, or sparkling options.

Rooms

The hotel boasts thoughtfully designed rooms with plush pillow top beds and high-definition TVs equipped with streaming capability. Back Bay King rooms offer a king bed and spacious walk-in showers ideal for a comfortable stay. South End Corner King rooms feature additional natural light and partial city views.

Location

Staypineapple is situated in Boston's South End, just steps from Back Bay and close to major historical sites. Guests have access to a direct train to Fenway Park in a quick 10-minute ride. The hotel is also within walking distance of trendy restaurants and art galleries in the area.

Dining

On-site dining is available at Trophy Room, offering all-American favorites and cocktails in a lively atmosphere. The menu provides a variety of options for breakfast, brunch, and dinner. Guests can join locals at the bar for a vibrant dining experience.

Pet-Friendliness

Staypineapple offers the Pineapple Pup Package for guests traveling with pets, including dog treats and a collapsible water bowl. The hotel is within walking distance of Peters Park and Boston Common, which offer off-leash areas. The dog-friendly policy ensures comfort for all visitors, including furry companions.

Highlights

Location: South End, steps from Back Bay

Dining: Trophy Room with all-American favorites

Amenities: The Naked Experience with cloud-like duvets

Pet-Friendly: Pineapple Pup Package for dogs

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
18 sq. feet
1 King-size bed
Coffee machine
Shower
Back Bay King
2 persons
18 sq. feet
1 King-size bed
Coffee machine
Shower

Price and Room Availability Calendar

Check availability and prices for your dates now!
July 2026 - July 2027
Sun
Mon
Tue
Wed
Thu
Fri
Sat
July 2026
27
28
29
30
31
1
2
August 2026
27
28
29
30
31
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
2
3
4
5
6
September 2026
31
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
1
2
3
4
October 2026
28
29
30
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
November 2026
26
27
28
29
30
31
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
1
2
3
4
5
6
December 2026
30
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
2
3
January 2027
28
29
30
31
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
February 2027
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
March 2027
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
2
3
4
April 2027
29
30
31
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
1
2
May 2027
26
27
28
29
30
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
1
2
3
4
5
6
June 2027
31
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
1
2
3
4
Choose dates to see prices
Check-in/ Check-out

Facilities

Experience a variety of amenities at the boutique hotel, crafted to ensure your comfort and unforgettable moments
Facilities: Great
8.3/10Review 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
Show more

Staypineapple, A Delightful Hotel, South End Location

26 Chandler St, Boston, 02116
Getting around
  • City Centre
    Boston 20 min  ·  1.0 mi
  • Airports
    Logan (BOS) 13 min  ·  5.3 mi
    Worcester Regional (ORH) 116 min  ·  47.7 mi
  • Train
    Boston South Station 17 min  ·  4600 ft
  • Underground
    Back Bay Metro Station 5 min  ·  1400 ft
  • Bus
    Bus stop 2 min  ·  400 ft
Interested in seeing the Exclusive Early Booking Rate?
Unlock exclusive rates now!
Check Rates
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 the entire hotel 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:
8
Number of rooms:
56
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 732 verified reviews
8.6 /10
Great
84 %
Recommend
Breakfast
8.3/10
Cleanliness
8.9/10
Comfort
8.8/10
Facilities
8.3/10
Free WiFi
7.4/10
Location
9.1/10
Paid Wi-Fi
8.6/10
Staff
9.1/10
Value for money
8.1/10
Guest reviews
based on 61 reviews
3.5/5
based on 862 reviews
8.5/10
No reviews yet on our siteUnfortunately, our guests have not yet left any reviews for this hotel, but you can read reviews from Booking.com.
Open reviews

Next best alternative

Consider them for your next trip.