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All cities · Boston · Staypineapple, A Delightful Hotel, South End

This ended 29 Sep 2026. The page stays up because the record is the point — the price below is what we recorded, not what you can book now.

Price record · 29 Sep 2026

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 photosPhotos from our rates supplier.

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

Staypineapple, A Delightful Hotel, South End — $102 a night, 36% below its normal rate

Well below typicalmeasured over 13 nightsHow we measured this →

Staypineapple, A Delightful Hotel, South End, Boston. 4-star, room only. 1 night from Sunday 27 December 2026, 2 adults, refundable. Normally $158; posted at $102.

Verified bookable at the supplier when published, 29 Sep 2026, 06:03 UTC — 45d ago. Written 29 Sep 2026, from the numbers as they stood then.

This room’s own readings

the series the claim was measured against
13 Dec 202610 Feb 2027

90-day median now $11090-day median when published $158this stay’s check-in, 27 Dec

This room, 1 night, 2 adults, priced 90 days ahead — one reading a night, so each is a different check-in date · 7 nights not measured, shown dotted
How we measured this

We’ve recorded 53 nights of prices for this room at a 90-day lead; their 90-day median is $110. The claim was measured against this room’s 90-day median at publication, $158. At publication this stay was $102 for 1 night.

Show the 53 readings
DateNightly rate
13 Dec 2026$102
14 Dec 2026$102
15 Dec 2026$235
16 Dec 2026$102
17 Dec 2026$241
18 Dec 2026$213
19 Dec 2026$215
20 Dec 2026$195
21 Dec 2026$193
22 Dec 2026$158
23 Dec 2026$156
24 Dec 2026$151
27 Dec 2026$102
2 Jan 2027$216
3 Jan 2027$188
4 Jan 2027$102
5 Jan 2027$202
6 Jan 2027$100
7 Jan 2027$104
8 Jan 2027$99
9 Jan 2027$118
10 Jan 2027$98
11 Jan 2027$99
12 Jan 2027$108
13 Jan 2027$102
14 Jan 2027$102
15 Jan 2027$192
16 Jan 2027$203
17 Jan 2027$158
18 Jan 2027$102
19 Jan 2027$128
20 Jan 2027$118
21 Jan 2027$113
22 Jan 2027$104
23 Jan 2027$191
24 Jan 2027$102
25 Jan 2027$100
26 Jan 2027$127
27 Jan 2027$110
28 Jan 2027$111
29 Jan 2027$110
30 Jan 2027$112
31 Jan 2027$139
1 Feb 2027$102
2 Feb 2027$98
3 Feb 2027$102
4 Feb 2027$98
5 Feb 2027$192
6 Feb 2027$193
7 Feb 2027$166
8 Feb 2027$98
9 Feb 2027$100
10 Feb 2027$102

How we check a price →

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

Back Bay KingThis deal

Back Bay King — the supplier's photographs — photo 1Back Bay King — the supplier's photographs — photo 2Back Bay King — the supplier's photographs — photo 3Back Bay King — the supplier's photographs — photo 4Back Bay King — the supplier's photographs — photo 5Back Bay King — the supplier's photographs — photo 6
Photos from our rates supplier.
Sleeps
2, up to 1 of them a child
Size
18 m²
Beds
1 extra-large double bed (super-king size), 181–210 cm wide
Board
Room only

This double room features a tea and coffee maker and a flat-screen TV with streaming services. The unit has 1 bed.

In this room

  • Coffee/tea maker
  • Shower
  • TV
  • Hair dryer
  • Coffee machine
  • Bottle of water
The other room types this hotel lists (1) — none of them is this deal

These are not part of this deal. We have measured no price for them, and the button above books only the room named above.

  • 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
Hotel policies
  • 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.
Staypineapple, A Delightful Hotel, South EndBoston · Hotel location

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Everything about Staypineapple, A Delightful Hotel, South End, and every price we have for it →

How this hotel behaves

median for one refundable night, 2 adults, from today forward · 168 forward prices across 12 months

In December a single refundable night here runs $161 at the median.

$194Nov ’26
▼ this stay$161Dec ’26
$113Jan ’27
$174Feb ’27
$266Mar ’27
$330Apr ’27
$415May ’27
$406Jun ’27
$356Jul ’27
$338Aug ’27
$294Sep ’27
$333Oct ’27

Lower Near average Higher12-month median $312/night

In December a single refundable night here runs $161 at the median. This deal is the same kind of night, priced 90 days ahead and the claim above compares it with this room’s own 90-day median at the same stay length and lead, not with these one-night rates. On the last sweep, among the 28 comparable hotels, this room was 1st cheapest.

Cheapest and dearest months, and every way we price this room →

Not these dates?

the cheapest nights we have priced at this hotel, in date order
  1. Mon, 7 Dec 2026$93
  2. Sun, 13 Dec 2026$102
  3. Tue, 15 Dec 2026$100
  4. Wed, 6 Jan 2027$102
  5. Sun, 10 Jan 2027$104
  6. Thu, 14 Jan 2027$102
  7. Mon, 18 Jan 2027$102
  8. Sun, 24 Jan 2027$100
  9. Tue, 26 Jan 2027$102
  10. Mon, 1 Feb 2027$100
  11. Wed, 3 Feb 2027$104
  12. Tue, 9 Feb 2027$100

Prices we recorded for one refundable night, two adults — not offers, and not this deal’s stay. Book opens our checkout, which re-prices that night with the hotel first; the live rate may differ from the one we recorded.

Every night we’ve priced here →

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