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Staypineapple A Delightful Hotel South End Boston

26 Chandler Street, Boston, MA 02116
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Traveler (148)
Room & Suite (54)
Dining (8)
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About

#33 of 95 hotels in Boston
Location
Cleanliness
Service
Value
Travelers' Choice
Staypineapple Boston is the perfect launching point for your Boston experience whether you’re taking a walk along the Freedom Trail, in town on business, or looking to catch a game with one of Boston’s storied teams. Our location is in one of Boston’s finest neighborhoods, Back Bay, and puts you just steps away from many of the city’s famous historical sites, stylish stores, and great restaurants. Staypineapple Boston will help you relax while working on your accent in private with all the elements and comfort of The Naked Experience and Staypineapple amenities, giving you a modern hotel experience in one of our country’s most historic cities.
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Property amenities
Free High Speed Internet (WiFi)
Bar / lounge
Bicycle rental
Bicycles available
Pets Allowed ( Dog / Pet Friendly )
Baggage storage
Non-smoking hotel
24-hour front desk
Wifi
Restaurant
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Room features
Air conditioning
Housekeeping
Safe
Bottled water
Flatscreen TV
Room types
Non-smoking rooms
Good to know
HOTEL CLASS
HOTEL STYLE
Residential Neighborhood
Mid-range
Languages Spoken
English
506Reviews9Q+A84Room tips
Traveler rating
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Stephanie A wrote a review Feb 24
1 contribution
Love this place! Would highly recommend. The rooms are quiant and the place has a great vibe. The pizzas are delicious, they have the best crust. 😋 The drinks are always on point and the bartenders are very friendly. We loved Eddie! Will be back again soon!
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Date of stay: February 2024Trip type: Traveled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
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D C wrote a review Feb 24
Oxford, United Kingdom48 contributions18 helpful votes
The hotel is modern, clean, and quite original in the stylings. The room was fairly small but not tiny. There isn’t a wardrobe or dresser for clothes, just a few hangers on the wall. This is probably the only negative about the place. The bed was very comfortable. We weren’t sure about the two individual duvets, but it wasn’t an issue, just unusual. The location is decent, with a 7-11 on the same block, Back Bay subway a 5 minute walk, Prudential Centre 15 minutes away and downtown 15 minutes away. If we were to revisit Boston we would probably stay here again. Also, the staff were brilliant. Jeff being fantastic on the front desk and deserving of a special mention as he is a real asset of the hotel.
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Date of stay: February 2024
Value
Location
Service
Trip type: Traveled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
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HappyTraveler1987X4 wrote a review Feb 19
New Hampshire2 contributions1 helpful vote
Super good value! Clean room with everything you need. Room and bathroom were small but who cares! Great options for restaurants around- easy walking to everything we did in the city- saw a show, bruins, game, lots of eating great food. Would definitely recommend. The only drawback was we could not regulate the heat in the room- we even asked for help from the front desk. Room was way too hot for good sleeping. We opened the window ( February) which helped but didn’t feel good environmentally.
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Date of stay: February 2024
Value
Location
Service
Trip type: Traveled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
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Response from MJ Mauhad, Guest Services / Front Office at Staypineapple A Delightful Hotel South End Boston
Responded 1 week ago
Thank you very much for staying with us here at Staypineapple Boston, we are so pleased to know that you enjoyed your stay. We hope your future travel plans will bring you back our way again soon, and we look forward to welcoming you back for another great Staypineapple experience! Thank you and best regards, MJ
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This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
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Dana wrote a review Feb 5
New York City, New York1 contribution
This was an odd hotel. We had to change rooms as there was an odd smell, so the front desk quickly offered another. There were two large dogs "staying" next door that barked every time we opened the door, so we tiptoed around a lot. The hotel is pretty, but the rooms are the tiniest I've ever stayed in. You can barely turn around in the bathroom. Also, the windows need to be changed as it was so drafty that we heard the highway all night (and had to stuff towels along the edge to keep the wind out). I love boutique hotels but I wouldn't recommend this one, despite it's fun and quirky edge and good location.
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Date of stay: January 2024Trip type: Traveled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
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Response from MJ Mauhad, Guest Services / Front Office at Staypineapple A Delightful Hotel South End Boston
Responded 3 weeks ago
Thank you for your review and sharing your feedback. We sincerely apologize for not meeting your expectations. We have noted your feedback regarding your experience, and are taking steps to ensure this is being addressed. We really appreciate you bringing this to our attention as it is so important to us to provide extraordinary service, and we can’t do that without you letting us know when we miss the mark. We sure hope you will give us another opportunity - please reach out to me at so we can make it right. Thank you and best regards,
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This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
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Discover779347 wrote a review Jan 2024
Martha's Vineyard, Massachusetts3 contributions
For Boston, this is a great value. Located in the South End it is steps into downtown, of chic South End business district. There are nice extras here such as a complimentary wine/beer or from the drink/snack fridge, generous channel selections on a generously sized flatscreen, delicious morning coffee or tea in the room machine. I am sure I could easily spend more for less of an accommodation.
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Date of stay: January 2024
Value
Location
Service
Trip type: Traveled solo
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
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Response from MJ Mauhad, Guest Services / Front Office at Staypineapple A Delightful Hotel South End Boston
Responded Jan 19, 2024
Wooohoo!! Thank you for this awesome review!! MJ
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This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
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Sean W wrote a review Jan 2024
Denver, Colorado2 contributions1 helpful vote
The entire pineapple theme here is one of the most charming and fun aspects of a hotel I've been to. The downstairs bar is great, and the location in South End is perfect for walkability. On top of all that, the check-in and checkout process was super easy and smooth.
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Date of stay: December 2023Trip type: Traveled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
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Response from Ben G, Other at Staypineapple A Delightful Hotel South End Boston
Responded Jan 14, 2024
Thank you very much for staying with us here at Staypineapple Boston, we are so pleased to know that you enjoyed your stay. We hope your future travel plans will bring you back our way again soon, and we look forward to welcoming you back for another great Staypineapple experience! Thank you and best regards, Ben/Food and Beverage Manager
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This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
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Jesse P wrote a review Dec 2023
2 contributions
I don't like booking with this company. The room is fine. Small, but basically clean and functional. I really don't like their extra "amenity fee" which they charge separately (about $23 per day). You are not offered the opportunity to waive the amenity fee and they don't discuss it during check in. I supposedly covers the availability to use their bicycles but they also incorporate wifi in the charge. It's a hidden expense and I hate that. One day there were sewer gases bubbling up through the toilet in several rooms. Horrible smell in the bathroom. They reacted quickly fixed the issue by the next night. As an apology they offered to waive the amenity fee (for those specific days only) but in the final receipt that didn't come out. So I had to call and explain. They removed it but it was an extra hassle. The rates fluctuate day by day so you don't get a locked in rate when you book. You just see after your invoice what they charged you each day. They told me this was normal but i've actually not encountered that before. I don't like companies that work in sneaky fees. Just give the full amount up front.
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Date of stay: October 2023Trip type: Traveled on business
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
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Response from MJ Mauhad, Guest Services / Front Office at Staypineapple A Delightful Hotel South End Boston
Responded Dec 22, 2023
I want to start by expressing our sincere apologies for the less-than-pleasant experience you had during your recent stay at StayPineapple Boston. Your comfort and satisfaction are our top priorities, and we deeply regret that we fell short of your expectations. I would like to assure you that we take your feedback seriously and have taken immediate action to address the issues you encountered. We have thoroughly reviewed your concerns and have made necessary improvements to prevent such issues from happening again in the future. Please do not hesitate to reach out to me at mmauhad@staypineapple.com, once again, I want to extend my sincere apologies for the inconvenience you experienced during your stay. We value your feedback as it helps us improve our services. We hope to have the opportunity to welcome you back in the future and provide you with the exceptional experience that you deserve. Thank you for choosing StayPineapple Boston, and again please feel free to contact me personally if there is anything else I can assist you with. Warm regards, MJ
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This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
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Su B wrote a review Dec 2023
Amesbury, United States2 contributions
I truly enjoyed my recent stay at Staypineapple Boston. The location is ideal, walking to Copley Square and the South End. The Back Bay T station is very close, as is the Silver Line. The bed and bedding were extremely comfortable, and the room was well-appointed. The staff was very helpful, including getting me into my room a few minutes early. The only thing that surprised me was the extra amenities fee, which was unexpected. But, I have heard that they are not the only hotel doing the same.
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Date of stay: December 2023
Value
Location
Service
Trip type: Traveled solo
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
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Response from Ben G, Other at Staypineapple A Delightful Hotel South End Boston
Responded Dec 20, 2023
Thank you so much for choosing to stay with us at Staypineapple Boston and for offering such excellent feedback. We always aim to offer comfortable accommodations and an unsurpassed degree of personalized service. I am thrilled to hear you found our service amazing and everyone so helpful and sweet! Thank you and best regards, Ben/Food and Beverage Manager
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This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
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Vacation47663971778 wrote a review Dec 2023
1 contribution
One of the worst hotel experiences I've had in a long time. Windows are old and drafty, hear street noise and cold all night long. To make matters worse, there are only these comforters, no sheets. Tiny room, teeny bathroom. No closets only hooks. No hotel security anyone from the street can just walk into the elevator and go upstairs. Main hotel door broken so handicap access is non existent.
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Date of stay: December 2023
Value
Location
Service
Trip type: Traveled solo
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Helpful
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Response from MJ Mauhad, Guest Services / Front Office at Staypineapple A Delightful Hotel South End Boston
Responded Dec 12, 2023
I want to start by expressing our sincere apologies for the less-than-pleasant experience you had during your recent stay at StayPineapple Boston. Your comfort and satisfaction are our top priorities, and we deeply regret that we fell short of your expectations. I would like to assure you that we take your feedback seriously and have taken immediate action to address the issues you encountered. We have thoroughly reviewed your concerns and have made necessary improvements to prevent such issues from happening again in the future. Please do not hesitate to reach out to me at mmauhad@staypineapple.com, once again, I want to extend my sincere apologies for the inconvenience you experienced during your stay. We value your feedback as it helps us improve our services. We hope to have the opportunity to welcome you back in the future and provide you with the exceptional experience that you deserve. Thank you for choosing StayPineapple Boston, and again please feel free to contact me personally if there is anything else I can assist you with. Warm regards, MJ
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This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
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Judi F wrote a review Dec 2023
1 contribution
It's the "Delightful" hotel with the funny name --- but nothing funny about their service! This was a new hotel brand for me and I was skeptical before our arrival --- "it'll be too boutique-y" and "what's up with the dog on the bed?" BUT --- once I arrived, I was sold! Excellent, friendly and efficient service from Leidy at the Desk and Seth at the bar. The rooms are small, the bathroom tiny but clean, quiet and efficiently organized. All the amenities were there. We were very comfortable and the location is perfect. Just three blocks from the Back Bay Orange Line station. You can't beat it and I highly recommend!
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Date of stay: December 2023
Value
Location
Service
Trip type: Traveled as a couple
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
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Response from Ben G, Other at Staypineapple A Delightful Hotel South End Boston
Responded Dec 10, 2023
Thank you very much for staying with us here at Staypineapple Boston, we are so pleased to know that you enjoyed your stay. You made our pineapple day with the shoutout to our amazing pineapple team members ! We hope your future travel plans will bring you back our way again soon, and we look forward to welcoming you back for another great Staypineapple experience! Thank you and best regards, Ben / Food and Beverage Manager
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This response is the subjective opinion of the management representative and not of Tripadvisor LLC.
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PRICE RANGE
₱9,481 - ₱21,934 (Based on Average Rates for a Standard Room)
ALSO KNOWN AS
chandler hotel boston
FORMERLY KNOWN AS
The Alise Boston
LOCATION
United StatesMassachusettsBostonSouth End
NUMBER OF ROOMS
56
Prices are the average nightly price provided by our partners and may not include all taxes and fees. Taxes and fees that are shown are estimates only. Please see our partners for more details.
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STAYPINEAPPLE A DELIGHTFUL HOTEL SOUTH END BOSTON - UPDATED 2024 Reviews & Price Comparison (MA) - Tripadvisor

Frequently Asked Questions about Staypineapple A Delightful Hotel South End Boston
Which popular attractions are close to Staypineapple A Delightful Hotel South End Boston?
Nearby attractions include Blue Man Group (0.5 km), John Hancock Tower (0.5 km), and Lyric Stage Company of Boston (0.4 km).
What are some of the property amenities at Staypineapple A Delightful Hotel South End Boston?
Some of the more popular amenities offered include free wifi, an on-site restaurant, and a lounge.
What food & drink options are available at Staypineapple A Delightful Hotel South End Boston?
Guests can enjoy an on-site restaurant and a lounge during their stay.
What are some restaurants close to Staypineapple A Delightful Hotel South End Boston?
Conveniently located restaurants include Mike & Patty's, Mistral, and Davio's Northern Italian Steakhouse - Back Bay.
Are pets allowed at Staypineapple A Delightful Hotel South End Boston?
Yes, pets are typically allowed, but it's always best to call ahead to confirm.
Are there any historical sites close to Staypineapple A Delightful Hotel South End Boston?
Many travellers enjoy visiting Bites of Boston Food Tours (0.7 km), The Printing Office of Edes & Gill (2.5 km), and Old North Church & Historic Site (2.5 km).
Is Staypineapple A Delightful Hotel South End Boston accessible?
Yes, it offers wheelchair access. For specific inquiries, we recommend calling ahead to confirm.