Staypineapple, A Delightful Hotel, South End — buildingStaypineapple, A Delightful Hotel, South End — photo 2Staypineapple, A Delightful Hotel, South End — photo 3Staypineapple, A Delightful Hotel, South End — photo 4Staypineapple, A Delightful Hotel, South End — photo 5Staypineapple, A Delightful Hotel, South End — photo 6Staypineapple, A Delightful Hotel, South End — photo 7Staypineapple, A Delightful Hotel, South End — photo 8Staypineapple, A Delightful Hotel, South End — photo 9
View all 9 photos ↗Photos from our rates supplier.

Boston · 4-star hotel · 8.5/10 · 1,638 reviews

Staypineapple, A Delightful Hotel, South End — $175 a night for 7 nights, 33% below its normal rate

Well below typicalmeasured over 24 nights

Staypineapple, A Delightful Hotel, South End, Boston. 4-star, room only. 7 nights from Sunday 6 December 2026, 2 adults, refundable. Normally $1,828; today $1,229.

4-star hotel · 8.5/10 · 1,638 reviews · Verified bookable at the supplier when published, 7 Oct 2026, 12:11 UTC — 2h ago. Written 7 Oct 2026, from the numbers as they stood then.

This room’s own readings

the series the claim was measured against
median $1,828
This room, 7 nights, 2 adults, priced 60 days ahead — one reading a night, so each is a different check-in date
How we measured this

We’ve recorded 24 nights of prices for this room at a 60-day lead; their median is $1,828. The claim was measured against this room’s own median at publication, $1,828. At publication this stay was $1,229 for 7 nights.

Show the 24 readings
DateTotal for 7 nights
13 Nov 2026$3,165
14 Nov 2026$3,151
15 Nov 2026$3,090
16 Nov 2026$3,005
17 Nov 2026$2,806
18 Nov 2026$2,363
19 Nov 2026$1,916
20 Nov 2026$1,653
21 Nov 2026$1,416
22 Nov 2026$1,366
23 Nov 2026$1,289
24 Nov 2026$1,458
25 Nov 2026$1,677
26 Nov 2026$1,828
27 Nov 2026$1,926
28 Nov 2026$2,002
29 Nov 2026$2,046
30 Nov 2026$1,955
1 Dec 2026$1,876
2 Dec 2026$1,674
3 Dec 2026$1,271
4 Dec 2026$1,435
5 Dec 2026$1,219
6 Dec 2026$1,228

How we decide something is a deal →

Full price history for this room →

About this hotel

what our rates supplier lists for it

Photos

Staypineapple, A Delightful Hotel, South End — buildingStaypineapple, A Delightful Hotel, South End — photo 2Staypineapple, A Delightful Hotel, South End — photo 3Staypineapple, A Delightful Hotel, South End — photo 4Staypineapple, A Delightful Hotel, South End — photo 5Staypineapple, A Delightful Hotel, South End — photo 6Staypineapple, A Delightful Hotel, South End — photo 7Staypineapple, A Delightful Hotel, South End — photo 8Staypineapple, A Delightful Hotel, South End — photo 9
Photos from our rates supplier.

4-star hotel · 8.5/10 · 1,638 reviews · Boston

26 Chandler Street, MA 02116 Boston
Check-in from 16:00 · check-out by 12:00

What guests scored

What guests scored over 1,638 reviews · Calculated 10 Dec 2025

Service
9.1
Value for Money
9.1
Location
8.7
Amenities
8.6
Overall Experience
8.6
Cleanliness
8.1
Food and Beverage
8.1
Room Quality
7.6

The property

Charming European-Style Boutique Hotel in Boston's South End

Modern Amenities: Each room at Staypineapple, South End boasts a flat-screen TV, iPod docking station, and a luxurious walk-in marble shower in the private bathroom.

Convenient Services: Guests can enjoy free WiFi, a work desk, and a direct line to the 24-hour front desk for any needs that may arise during their stay.

Prime Location: Situated in the historic South End, the hotel is just a short stroll away from renowned restaurants and attractions, including the vibrant Back Bay area and upscale shops on Newbury Street.

Ready to experience the perfect blend of comfort and sophistication? Book your stay at Staypineapple, South End now!

The room in this deal

Deluxe King

room only

This is the room the price was measured on and the room the button books. The hotel lists its rooms under different names, so we could not match this one to the supplier’s own photograph and description — they are in the fold below, unmarked, because guessing which is this one would be a claim we have not checked.

Every room type this hotel lists (2)

Every room type the hotel lists. We priced one of them for this deal — the rate card names it — and we have no measured price for the others.

  • Back Bay Kingsleeps 2, up to 1 of them a child · 18 m² · 1 extra-large double bed (super-king size), 181–210 cm wide
  • South End Corner Kingsleeps 2, up to 1 of them a child · 18 m² · 1 extra-large double bed (super-king size), 181–210 cm wide

Facilities

What the hotel lists

  • Free WiFi
  • Air conditioning
  • Restaurant
  • Bar
  • Lift / Elevator
  • Pets allowed
  • 24-hour front desk
  • Luggage storage
and 20 more

In the room

  • Heating
  • Staff adhere to local safety protocols

Services

  • Daily housekeeping
  • Concierge service
  • Laundry washed per local authority guidelines

Families and pets

  • Pet bowls
  • Pet basket

Accessibility and safety

  • Non-smoking throughout
  • Fire extinguishers
  • First aid kit available
  • Smoke alarms

Other

  • Cashless payment available
  • Guest rooms disinfected between stays
  • Cleaning standards that are effective against Coronavirus
  • Hand sanitizer in guest room and key areas
  • Sanitized tableware & silverware
  • Invoice provided
  • Guests can opt-out any cleaning services during stay
  • Face masks for guests available
  • Key card access
Good to know before you book
  • Pets are not allowed.
  • Children are welcome.
  • Please note, guest must be a minimum of 18 years of age to check in.
  • Please note that, Reservations for 10 rooms or more need to be contracted as a Group with the hotel directly.Guests are required to show a photo ID and credit card upon check-in. Please note that all Special Requests are subject to availability and additional charges may apply.
  • A deposit may be required at the property.
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$1,229

7 nights from 6 Dec 2026