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 — $762 for 7 nights, 71% below its normal rate

Rare pricemeasured over 56 nightsHow we measured this →

Staypineapple, A Delightful Hotel, South End, Boston. 4-star, room only. 7 nights from Tuesday 8 December 2026, 2 adults, refundable. Normally $2,619; today $762.

Re-checked with the supplier 5h ago, and verified bookable when published. Written 9 Nov 2026, from the numbers as they stood then.

This room’s own readings

the series the claim was measured against
14 Oct 20268 Dec

Total for 7 nights90-day median now $2,62090-day median when published $2,619this stay’s check-in, 8 Dec

This room, 7 nights, 2 adults, priced 30 days ahead — one reading a night, so each is a different check-in date
How we measured this

We’ve recorded 56 nights of prices for this room at a 30-day lead; their 90-day median is $2,620. The claim was measured against this room’s 90-day median at publication, $2,619. At publication this stay was $762 for 7 nights.

Show the 56 readings
DateTotal for 7 nights
14 Oct 2026$4,343
15 Oct 2026$4,396
16 Oct 2026$4,095
17 Oct 2026$4,200
18 Oct 2026$4,021
19 Oct 2026$3,953
20 Oct 2026$4,026
21 Oct 2026$3,586
22 Oct 2026$3,791
23 Oct 2026$3,825
24 Oct 2026$3,166
25 Oct 2026$3,096
26 Oct 2026$2,704
27 Oct 2026$2,819
28 Oct 2026$2,681
29 Oct 2026$2,599
30 Oct 2026$2,688
31 Oct 2026$2,939
1 Nov 2026$3,109
2 Nov 2026$3,050
3 Nov 2026$2,876
4 Nov 2026$2,872
5 Nov 2026$2,648
6 Nov 2026$2,423
7 Nov 2026$1,980
8 Nov 2026$1,489
9 Nov 2026$1,557
10 Nov 2026$1,919
11 Nov 2026$2,617
12 Nov 2026$2,970
13 Nov 2026$3,015
14 Nov 2026$3,016
15 Nov 2026$2,721
16 Nov 2026$2,620
17 Nov 2026$2,384
18 Nov 2026$1,905
19 Nov 2026$1,462
20 Nov 2026$1,398
21 Nov 2026$1,288
22 Nov 2026$1,191
23 Nov 2026$1,162
24 Nov 2026$1,248
25 Nov 2026$1,338
26 Nov 2026$1,344
27 Nov 2026$1,289
28 Nov 2026$1,011
29 Nov 2026$1,180
30 Nov 2026$1,131
1 Dec 2026$1,293
2 Dec 2026$1,239
3 Dec 2026$1,306
4 Dec 2026$1,382
5 Dec 2026$1,120
6 Dec 2026$798
7 Dec 2026$732
8 Dec 2026$762

How we decide something is a deal →

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
  • 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 · 169 forward prices across 12 months
$180Nov ’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 usual Higher12-month median $312/night

November 2026: $180 a night. December 2026: $161 a night. January 2027: $113 a night. February 2027: $174 a night. March 2027: $266 a night. April 2027: $330 a night. May 2027: $415 a night. June 2027: $406 a night. July 2027: $356 a night. August 2027: $338 a night. September 2027: $294 a night. October 2027: $333 a night.

In December a single refundable night here runs $161 at the median. This deal is a different product — 7 nights, refundable, priced 30 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 30 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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Spotted a stale price or dead link? Tell us → · How we decide something is a deal

$762 71% below

7 nights from 8 Dec 2026