A Delightful Hotel
Boston South End
Map Attractions 26 Chandler Street
Boston, MA, 02116
(857) 444-6111

Fall “In Sleep” With Us

Best Rate Guaranteed
View or modify a reservation

A "Wicked Smaht" Choice in South End

Staypineapple Boston

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, the South End, just steps away from Back Bay and 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.

“Weekend Getaway”

This is a charming hotel located in a quite area of downtown Boston and very walkable to restaurants and all the major historical sites. The rooms are whimsical with very clever pineapple themed amenities.

Departure48546434709, 07/04/2019 5 star review

“Staypineapple REALLY is delightful”

This affordable boutique was a pleasure to stay at. The decorations were incredibly charming. I absolutely love the South End part of Boston. Great restaurants and bars in short walking distance.

UAPrima, 07/06/2019 5 star review

SPECIAL OFFERS

Advance Purchase

Plan now, stay later and save more, plus $25 to spend how you want!

Learn More

Pineapple Pup Package

Get pup peace-of-mind and fun extras with this package for your furry family members.

Learn More

What's nearby

Staypineapple Boston
26 Chandler Street, Boston 02116, United States Entrance of Staypineapple Boston
Phone: (857) 444-6111
Points of Interest Near the Hotel
Place Name Address Phone Distance Show on map
Fenway Park 4 Yawkey Way, Boston, MA 02215 5267.19
Boston Common 139 Tremont St, Boston, MA 02111 5265.57
TD Garden 100 Legends Way, Boston, MA 02114 5265.69
Faneuil Hall Marketplace 4 S Market St, Boston, MA 02109 5265.2
Copley Square Copley Square Boston, MA 02116 5266.15
Museum of Fine Arts 465 Huntington Ave, Boston, MA 02115 5266.85
New England Aquarium 1 Central Wharf, Boston, MA 02110 5264.93
Boston Opera House 539 Washington St, Boston, MA 02111 5265.5
Massachusetts State House 24 Beacon St, Boston, MA 02133 5265.65
Freedom Trail Freedom Trail Boston, MA 5265.33
Back Bay Station 145 Dartmouth St, Boston, MA 02116 0.32
Logan Airport 1 Harborside Dr, Boston, MA 02128 3.04
This is a Google Map and is inaccessible by screen reader.