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8.3

866 reviews

Staypineapple, A Delightful Hotel, South End

Staypineapple, A Delightful Hotel, South End

26 Chandler Street, Boston, 02116, Massachusetts, United States

Reservations:

+1-833-728-2041

Choose dates to view prices

Restaurant

Adults only

Free wifi

Air conditioning

Bar

24-hour front desk

Non-smoking rooms

Elevator

Staypineapple, A Delightful Hotel, South End

Welcome to Staypineapple, A Delightful Hotel, located in the vibrant South End neighborhood of Boston. With its charming decor and delightful amenities, this 4-star hotel offers a truly memorable stay for travelers seeking a unique experience.

Situated at 26 Chandler Street, Staypineapple is conveniently located just 1mi from the city center, making it the perfect base for exploring all that Boston has to offer. With 866 glowing reviews, it's clear that guests are consistently impressed by the exceptional service and luxurious accommodations provided by the hotel.

The rooms at Staypineapple are equipped with all the essentials for a comfortable stay, including free WiFi, air conditioning, and free toiletries. The hotel also offers a range of additional amenities, such as a 24-hour front desk, a bar, and an on-site restaurant. Whether you're traveling for business or leisure, Staypineapple provides a relaxing and inviting atmosphere for guests to relax and unwind.

So why wait? Book your stay at Staypineapple, A Delightful Hotel, South End, Boston today and experience the charm and hospitality that this unique hotel has to offer. Prices start from $130, so don't miss out on this delightful destination in the heart of Massachusetts.

When it comes to dining options, Staypineapple, A Delightful Hotel has you covered. On-site, you'll find the Trophy Room, a modern restaurant offering delicious American cuisine. Whether you're in the mood for a hearty breakfast to kickstart your day or a flavorful dinner to satisfy your taste buds, the Trophy Room provides a delightful dining experience. Immerse yourself in the vibrant ambience and indulge in the mouthwatering dishes prepared by the talented chefs. So, whether you're craving a classic burger or exploring the diverse flavors of American cuisine, the Trophy Room offers a culinary journey that will leave you satisfied and craving more.

At Staypineapple, convenience is key, and that includes the payment options. Cash is not accepted, but fear not, as the hotel accepts a variety of payment methods to ensure a hassle-free transaction. From Diners Club to American Express, from Mastercard to UnionPay, you can choose the payment method that suits you best. So whether you prefer to tap your card or swipe it, you can rest assured that your stay at Staypineapple will be a seamless experience, starting from the moment you arrive to the time you check out.

Now let's talk about the rooms. Staypineapple offers two types of double rooms, each designed to provide a delightful stay. The Corner King Room, with its cozy 194 square feet, offers ample space for relaxation. Equipped with a comfortable king-size bed, it can comfortably accommodate two adults. If you're looking for a touch of luxury, the Deluxe King Room is the perfect choice. With the same room size and bed type as the Corner King Room, it provides a spacious and inviting atmosphere for a truly memorable stay. Whether you're traveling with a loved one or you simply enjoy the extra room to stretch out, the Deluxe King Room promises a delightful experience throughout your stay. So, why wait? Book your stay at Staypineapple, A Delightful Hotel, South End, Boston, and immerse yourself in the charm and hospitality that this unique hotel has to offer.

Prices start from $130, so don't miss out on this delightful destination in the heart of Massachusetts. With its prime location, delightful amenities, mouthwatering dining options, and comfortable rooms, Staypineapple, A Delightful Hotel is the perfect choice for travelers seeking a unique and memorable experience in Boston.

Closest airports

Logan International Airport

3mi

Manchester Airport

44.3mi

New Bedford Regional Airport

46.8mi

Theodore Francis Green State Airport

46.8mi

Provincetown Municipal Airport

47.5mi

Most popular amenities

Restaurant

Adults only

Free wifi

Air conditioning

Bar

24-hour front desk

Non-smoking rooms

Elevator

Free toiletries

Rooms

Corner King Room in Staypineapple, A Delightful Hotel, South End

Show 10 photos

Corner, King

1 King Size Bed

195 sqft

Private Bathroom

Flat-screen TV

Tea/Coffee maker

Shower

+

More details

Relax in our cozy Corner King Room, a spacious 194 sqft double room featuring a comfortable King size bed, a private bathroom with shower and free toiletries, a flat-screen TV, and convenient amenities like a tea/coffee maker and hairdryer. Smoking is not allowed in this room. Ideal for couples or solo travelers looking for comfort and convenience.

Show 10 photos

South End Corner, King

1 King Size Bed

190 sqft

Wifi

x10

+

x6

More details

South End Corner King includes a king-size bed 150-183 width.

Show 6 photos

King Room, Bay View

1 King Size Bed

190 sqft

Wifi

x10

+

x6

More details

Back Bay King includes a king-size bed 150-183 width.

Deluxe King Room in Staypineapple, A Delightful Hotel, South End

Show 9 photos

Deluxe

1 King Size Bed

195 sqft

Private Bathroom

Flat-screen TV

Tea/Coffee maker

Shower

x4

+

x3

More details

Room

Show 6 photos

Standard Room

1 King Size Bed

x4

+

x3

More details

Boutique, Queen

1 Queen Size Bed

Free wifi

Flat-screen TV

+

More details

Economy, Queen

1 Queen Size Bed

Free wifi

+

More details

Boutique, Twin

1 Twin Bed

Free wifi

Flat-screen TV

+

More details

Run of House

x10

+

x6

More details

Room Run Of House

South Corner, King

1 King Size Bed

+

More details

Guest reviews

8.3

866 reviews

Categories of assessments

Cleanliness

Comfort

Location

Facilities

Staff

Value for money

WiFi quality

Featured reviews:

🇬🇧

Dorothy

8.2

September 2022

No breakfast provided

Boston/local govt is not helping itself. There are taxes added to your hotel fee of 14.95% : this is not staypineapple but the local government State Room Occupancy Excise Tax Rate - 5.7% Boston Local Room Occupancy Excise Tax - 6.5% Convention Center Funding Tax - 2.75% That all equals 14.95% so annoying and takes the edge of what could be a great stay

🇬🇧

Erin

10

July 2023

AMAZING stay in Boston for 5 days with my partner. Holiday from my dreams. I booked this hotel because it seemed like a cute, modern, quirky hotel that also had a great location. I was not disappointed. Easy to reach - you take a free shuttle from the airport to the blue line station, then you get on the blue line towards State, then you switch to the orange line and go towards Back Bay, then its a short 5 minute walk to the hotel. And the opposite of course, on the way back home. The subway is so easy to use and it's only a couple of dollars for each ride. We walked everywhere tbh because we like not having to drive on holiday, and everything worth seeing and doing was within a 45 minute walk. The hotel itself is so cute and really friendly. We drank at the bar the first couple of nights and it was nice and chill. The hotel is spotlessly clean and everyone is so friendly. It's a really quirky room with pineapple themed everything including fluffy robes, pillows, towels etc. There's a wee dog stuffed animal in the room (called Dash the pineapple pup!) (I think it's a very pet friendly hotel) and I paid $25 to 'adopt' him and got to take him home. I plan on visiting Boston again in the future and I would 100% stay at this hotel again.

🇺🇸

Brenda

10

August 2023

Everything was amazing! We arrived later in the evening, perhaps around 9:30. The gentleman that was working had energy and was so very kind. The room was wonderful. It was my husband's birthday trip and even I was surprised with the detail and thought placed into making it a memorable first impression. The pineapple theme is one of a kind and fabulous!!!!! Everything was beautiful. The bed was comfortable. The staff was always engaging and extremely friendly. I cannot say enough!

That question shouldn't even have to be asked. Everything was beyond exceptional and if there is ever anything wrong, it is not on the hotel, staff, or anything else.

🇨🇦

Patricia

8.2

September 2023

Let's face it - the theme for this place is CUTE, and the pictures are pretty much on point. The room itself did not disappoint, other than it was fairly small to fit a king-sized bed, but for a two-night stay for a couple who does not spend their vacation time in their hotel room, it was just fine for us. The amenities inside the room were as described. The location worked for our stay. We walked to the Quincy Market one night (20-25 minutes), and we took a quick subway ride (3 stops, if I recall correctly, but a 6-7 minute walk to the closest subway station) to Fenway for a Red Sox game the second night. Boston hotels are expensive in the summer, but overall, I think we had a pretty good rate for the room that we had.

I was surprised by the resort fee of $15USD per night. I don't recall if I saw that at the time of booking, and I don't think it would have prevented me from booking there, since it bought us all the water, coffee and tea that we could drink, but I am mentioning it here to perhaps prevent someone else from being caught off-guard by it upon arrival. The lovely pineapple cookies were only out in view when we first arrived. After that, we had to ask for them. We were always offered to "take as many as we wanted", but I felt weird having to ask for them, and then having the desk clerk watch while I took a handful.

🇺🇸

Melissa

9.1

July 2023

The room was clean, decor was great. Bedding is really nice. The hotel was quiet. The lobby staff were very nice & helped you out when needed (Jeff & James). Nice with the stay you each get 1 free drink, and the unlimited bottled water was a big plus for us. Umbrellas to use if needed. They put a bowl of water on the sidewalk for anyone’s dog. All around a nice, quiet hotel.

The room’s glass shower door has an engineering flaw. The water runs down the glass, under the door’s edge & out on the bath floor. No huge deal but will need to put a towel & dry it up so your feet don’t get wet.

🇦🇴

Jessica

10

June 2023

All the staff were simply impeccable! I literally just felt like I was home, because everyone was just so friendly and always happy to help. Honestly I can’t express enough how grateful I am for all the staff and the Manager! Had a brilliant stay with brilliant people! The rooms were really clean and tidy…. It’s really a naked experience! The Bar/Restaurant is also very nice and the food is good too! Will definitely recommend

🇨🇦

Manuela

8.2

July 2023

Ingenious way of having everything that is needed in such a small room.

The restaurant apparently ran out of coffee in the early evening. The staff there seemed to be unorganized- our waiter didn’t know what was available and what not- for the 5 choices of welcome free drinks. He also took our order for coffee and then returned saying they ran out. The waiter at next tabled forgot that the order for drinks was and then had another waiter serve that table. Also, the room didn’t have any tea available and the hair dryer was hiding in the drawer underneath the bed.

🇮🇱

David

8.2

March 2023

The staff was super friendly. The location is superb. The room was clean.

The room was small with no closet to put a suitcase. The mandatory "amenities" payment of 15 USD per day upfront for something I didn't use and didn't like was totally unjustified. It was just like a tax. You know what? Raise the room rate, but please stop this nonsense. I was really annoyed by this. The room was very noisy. The walls are not sound proof and I could not fell asleep until 1:00 AM, because in the room next to mine a TV was working loud. When they finally switched it off I could hear the conversations... Didn't like this at all.

🇺🇸

Marko

9.1

June 2022

The room was comfortable and clean. The location of the hotel is excellent. I covered the entire city by foot and found it very easy to get around with a base at the hotel. Having a bike available at the hotel was great, as I used it to get out to Cambridge and tour the Harvard campus with a beautiful ride along the way.

The resort fee is a bit confusing. I noticed that many of the other hotels are using a similar system, and maybe this is just a non-taxable service...however, you do not have an option to refuse it for the amenities included, so it would be nice to just include it into the hotel fees. Clearly, the cost of rooms in the center of the city are on the high end. Costs aside, the hotel was great, and staff were very kind and helpful.

🇺🇸

Janet

9.1

January 2023

Great amenities for the price! The room is small but very clean and all that you need for a short stay. Enjoyed the ambiance in the lobby/bar. Staff is friendly and helpful. Very central location in Boston -- walking distance to restaurants and shops in the Back Bay, Public Garden, both the orange and green subway lines.

Instructions on how to adjust the heat on check-in. Wall thermostat does not adjust and didn't find the remote control until the morning. If staying for multiple nights, a small chair to read or work in, rather than the bed, would be appreciated.

Points of Interest Around Staypineapple, A Delightful Hotel, South End

Attractions

Back Bay

0.4mi

Boston South End

0.4mi

Gibson House Museum

0.6mi

Louisburg Square

0.8mi

Vilna Shul

0.9mi

Old South Meeting House

0.9mi

Boston Old State House

1mi

Boston Massacre Site

1.1mi

MIT Museum

1.7mi

Cambridge Common

3.3mi

Longfellow House (Washington's Headquarters)

3.5mi

Battle Road Trail

13.5mi

Salem Witch Village

15.1mi

Concord

15.6mi

The Old Manse

16.5mi

Restaurants

Trophy Room

Cuisines

  • American

Ambiances

  • Modern

Amenities of Staypineapple, A Delightful Hotel, South End

Restaurant

Adults only

Free wifi

Air conditioning

Bar

24-hour front desk

Non-smoking rooms

Elevator

Free toiletries

Stay rules - Staypineapple, A Delightful Hotel, South End

  • Check-in / Check-out

  • Pets

  • Internet

  • Age restrictions

  • Parking

  • Reservations

  • Children and beds

  • Cards accepted at this property

Frequently Asked Questions - Staypineapple, A Delightful Hotel, South End

Are pets permitted at Staypineapple, A Delightful Hotel, South End?

Absolutely! You are more than welcome to stay with your beloved pet at Staypineapple, A Delightful Hotel, South End. Just keep in mind that there might be charges associated with bringing your furry friend along.

At what times are check-in and check-out at Staypineapple, A Delightful Hotel, South End?

For Staypineapple, A Delightful Hotel, South End, you can check in after 04:00 PM and the check-out deadline is 12:00 PM.

What are the rates at Staypineapple, A Delightful Hotel, South End?

Rates at Staypineapple, A Delightful Hotel, South End commence from $130. However, final pricing may depend on room choices and booking dates. Always input your stay dates for precise rates.

Which room categories can I book at Staypineapple, A Delightful Hotel, South End?

The Staypineapple, A Delightful Hotel, South End offers two types of rooms. The Corner King Room and Deluxe King Room both have a room size of 194 sqft and do not allow smoking. Both rooms can accommodate 2 adults and have one King size bed.

What activities does Staypineapple, A Delightful Hotel, South End offer?

Guests at Staypineapple, A Delightful Hotel, South End, can make the most of their time by exploring the leisure amenities offered. The hotel provides an adults-only environment, creating a peaceful and relaxing atmosphere for guests. They can unwind and enjoy their favorite cocktails at the bar, adding to their overall experience.

For those looking to explore the surroundings, the hotel also offers bicycle rentals. This gives guests the opportunity to head out and explore the area at their own pace, enjoying the scenic beauty and discovering new places.

To satisfy their cravings, guests can dine at the hotel's on-site restaurant, Trophy Room. The restaurant offers a modern ambiance and serves American cuisine, providing a delightful dining experience for guests.

With these leisure amenities and dining options available, guests at Staypineapple, A Delightful Hotel, South End, can enjoy a pleasant and fulfilling stay during their visit.

Are there restaurants located within Staypineapple, A Delightful Hotel, South End?

Yes, the hotel has a restaurant on site called Trophy Room. It offers a modern ambiance and serves American cuisine.

What methods of payment does Staypineapple, A Delightful Hotel, South End accept?

Staypineapple, A Delightful Hotel, South End accepts the following payment methods: Diners Club, Discover, American Express, Mastercard, Visa, and UnionPay. Unfortunately, the hotel does not accept cash.