Staypineapple

Although the room was smaller then expected overall we had a comfy stay we came to celebrate our 10 year anniversary with a mini stay and they were sweet and had a complementary champagne for us so thoughtful and made the trip even better we love the double duvet covers in the bed was quite comfortable and service team was great!

Comfortable, convenient hotel with really helpful and friendly concierge! The beds were clean, the water pressure and temperature was great, the AC works. The WiFi was a little slow at night and there was some noisy construction outside but that's outside of their control. Overall, I'd recommend!

Very accommodating

Staypineapple is a great hotel to stay in while in Boston. The location is very convenient and close to all the things you want to see when you are visiting the city. It is also close to the “T” station. The rooms are comfortable and clean. The staff are friendly and helpful. They go above and beyond to make your stay memorable. Erminia from the front desk specifically is someone who made our stay exceptional. I would recommend this hotel to everyone I know!

So funky and cool. The robes are to die for. Bar attached for a nightcap

Absolutely blown away by this hotel, probably the most comfortable bed I’ve ever slept on at a hotel better than those five star luxury hotels in my opinion. Extremely comfortable robes, cute and quirky rooms with the pineapple feed, amazing location, friendly staff and Gabe goes above and beyond helping guests. Will definitely be back here because of Gabe and the rest of the team and well forever be loyal to stay pineapple

StayPineapple is the cutest boutique hotel! The efficiency of the rooms made it feel cozy but had everything we need. The entire establishment smells so clean, IS so clean. I love the decorative touches, complementary drinks (alcoholic and non), partnership with supporting local animal shelters and especially how FRIENDLY and accommodating the staff are. It was perfectly located in a darling walkable neighborhood. We woukd definitely highly recommend and come back to stay again!

We stayed at the Boston location and our stay was great. Gabe did a great job taking care of us.

Had a wonderful visit at the Stay Pineapple Boston. The location was ideal and we were able to walk to all the different downtown neighborhoods. Mitchell was very pleasant and helpful!

I’m so glad I discovered Staypineapple. It has by far been my favorite hotel stay; I will certainly be staying at their designated locations in future cities I visit. The food was quality, most comfortable bed I’ve slept in at a hotel, I love how they offer bicycles for hotel guests to use leisurely, and loved the dog “hotel greeter” roaming the lobby, Gucci! I was so appreciative of the hotel staff’s customer service and friendliness. I was there for my birthday and the hotel decorated my room prior to check in, it was the best! Special thanks to the bartender / server, Olivia. Of all the great people I met in Seattle, she was one of my favorites. Thank you for being so kind, genuine, and welcoming, it means the world. It’s people like Olivia that makes traveling solo feel like home.

Perfect location, for walking to the Space Needle, Variety of resturants in walking distance, perfect location for the curise ports. The Staff amazing! Ecstatically pleasing to the eyes. The Bistro Very good! Comfortable bed!

This place went above and beyond, the staff really cared. I was being a tourist in my city lol, I'm so happy I chose Pineapple

Rooms are spacious! Linens are great, so comfy! Beds are so comfortable!! Very clean! Highly recommended! Great night sleep.

The StayPineapple literally saves our trip to Seattle ! We booked a room at the last minute because the first place we'd booked in the city didn't meet our expectations at all. And everything was PERFECT! Big, clean and comfy room. The staff is super friendly and there are plenty of little touches that make your stay easier. We would definitely stay again if we ever come back to Seattle!

Good location, walking distance to the space needle and grocery store.

This hotel is located around 7 minute s from the space Needle on foot. They do offer bicycles for use. Very cute!

Raúl at reception is fantastic, very professional and friendly. He helped us with everything we needed. The hotel is wonderful, and the pineapple theme adds a touch of joy to your vacation. We'll be back! Thanks, Raúl! 😍

The hotel is amazing and the staff is excellent! The decor is incredible, the drinks at the bar delicious. Raul at the front desk is very professional and took care of all our needs. This is a super friendly dog hotel but sll dog owners are mindful snd respectful. Will definitely come back

I love absolutely everything about this hotel...Staff, location, and all of the little extras that the hotel offers. So much thought has been put into the decor and atmosphere! Highly recommend!

Terry and Jerry at the front desk were absolutely wonderful! They were both incredibly friendly, attentive, and helpful throughout our stay. Their warm welcome and excellent customer service made us feel truly valued as guests. They are a great asset to the hotel and made our experience even more enjoyable. Thank you both!

Jaime from the front desk was absolutely wonderful! We couldn’t recommend him enough. He took great care of us from the time we walked into this beautiful place! It really made all the difference in our hotel stay! Greta hotel- would stay here again!!

The atmosphere was great and to top it off the receptionist Jamie was so great.

Jamie was great at check in. Very fast and efficient and professional. He made this check in process a very good experience. Definitely recommend.

Staypineapple has built a brand around their friendly staff and it’s has really made a difference. Jamie at the front desk was really helpful. The hotel is very pretty and the rooms are comfortable. Great stay.

Excellent location! Super cool theme. Terry at the front was the best! Give that man a promotion!

Super helpful staff, specially Mr Terry who helped a lot in giving local context and suggestions.

We had a wonderful time. Terry and Brian are very friendly and welcoming, and the space is peaceful and cheerful. Thank you so much!

We really enjoyed our stay! While we ran into a few minor issues with our room, the staff was unbelievably kind, attentive, and helpful in resolving them. Truly top-tier hospitality that's hard to come by these days. The room itself was clean and comfortable. The surrounding neighborhood isn't the best given its proximity to the Tenderloin, but overall, the exceptional service made for a great experience.

Brian was great with us. Everything great

Had an amazing experience during a weekend away for my birthday! Staff made us feel super welcome and surprised us with a special birthday gift in the room. The view and location were all perfect. 10/10 would stay here again.

I couldn’t be happier with my stay here. Came here for a very special occasion and the hotel rose to the occasion by decorating our room and provided complimentary prosecco which was just such a nice touch. The rooms themselves are comparable to other Loop hotels size wise in this price point, in my opinion. The hotel is in a historic building and it all feels very charming, even while under some construction which you really don’t notice. Our room was quiet with exception to some occasionally city noise but that’s to be expected. The shower was AMAZING, IMO. Now, maybe some may not be able to appreciate it but I VERY much appreciated the water pressure and the temp was on point. Close to all L lines and a short walk to Chicago Theater, Clerk’s Office/Marriage Court. Highly recommend and will stay again!

We’ve stayed at Staypineapple three times now, including having our wedding party stay there last year, and it’s been great every time. The staff is really friendly and helpful. They made things easy for our wedding group and were just as great during our most recent stay. Rooms are clean and comfortable, and the whole place has a fun vibe that makes it feel a bit different from a typical hotel. The comforters and robes are seriously so soft and comfortable, and the pineapple-shaped sugar cookies are a great touch. At this point it’s one of our go-to spots. Would definitely recommend.

Booked for a birthday trip. The rooms are amazing, second time staying here because the first time was so great. The staff are awesome and really helpful, and really came through with early check in, and making sure the room looked great. (Decorations were from me) but they offered us wine and a little treat to make the surprise even more special. The beds are seriously the best sleep you will ever get.

We are a group of 4 women that just completed our 3rd annual stay at Staypineapple. We get a floor to ourselves since there are only 4 rooms to a floor which makes us feel pretty special! The staff is great. We love the cookies, the incredibly comfortable beds and location is so convenient.

We absolutely love it here! Currently staying and it has been a wonderful experience. The hotel is beautiful, the service has been excellent and the rooms are very comfortable. We are celebrating my partners birthday and when we got to the room, there was called champaign and a balloon. Then we got back to the hotel late last night and the door man greeted us and gave us each a bottle of water. Thought it was the nicest touch. Would highly recommend!

What a perfect trip. Booking was easy. Check in was transparent and quick. Even came with welcome drinks! We were in town to see a play and the staff went above and beyond to welcome us. The location is great and walkable. The bartender is super friendly and makes a mean handcrafted cocktail. The beds are heaven. Pineapple cookies and coffee in the afternoon. But the real star that makes this property shine is the fabulous and creative general manager, Kristin. The attention to detail is better than any “5 star” property with amenities that you really need.

Cassandra was exceptional! Her service at the front desk truly made our Chicago trip unforgettable. The complimentary coffee and pineapple cookies every afternoon were a delightful touch. We also loved the free drink at the bar and the unlimited sparkling or still water—fantastic amenities. This hotel is truly one of a kind.

This place is amazing! The location is killer. The beds are like clouds. I took a gummy and woke up upside down in the bed I slept so hard. 😀 it’s so clean and quiet. The staff are great and the prices can’t be beat. A must stay!

We stay at StayPineapple in Chicago every time we go to the Windy City. The location is just a step away from the Art Institute, Millennium Park and some of our favorite restaurants ....like Eggys! We also love the food and bar at the Atwood right in the hotel. Sooo convenient and lovely. Choices for the adults and kids. Everyone is happy--especially with the free drinks that come with every visit. The folks at the desk are always helpful and even greet us personally when we arrive. Go on your birthday and you are treated like a queen. The building itself oozes with history because it was lovingly restored. I love staying a boutique hotel with excellent service rather than a huge multinational chain. I know I’m in Chicago. Love it!

We had a wonderful three-day stay at Staypineapple in Chicago! The hotel is beautiful, clean, and well-maintained. The staff truly go above and beyond to assist with any requests, which made our stay even more enjoyable. Our room was spotless and had a nice view of the street. The location is perfect - walking distance to The Bean, surrounded by great restaurants and shops, and very close to bus stops, making it super convenient for exploring downtown. We’d definitely stay here again on our next trip to Chicago!

Oh my goodness….we have lived in NW Indiana for 20 years and I don’t know how I’ve never stayed here. This is my new go to downtown staycation hotel. My bff and I had a superb stay to celebrate my 50th birthday. Kudos to Cassandra at the front desk for exceptional customer service and for making our stay amazing. The location, comfort of the beds, and sheer beauty of this historic building makes it a must for your next Windy City adventure!

Very cute for girls, kids, and some people that like feminine things. Flowers, butterflies, pastels.... The rooms are tiny. We got a connecting room, which was just 2 end rooms, we closed off the door to the hallway and left both room doors open. Then we had 2 bathrooms, a living area, and the bedroom. I enjoyed the atmosphere even though it was tiny. Everything was clean and in working order. The staff were friendly and helpful. I would go back, especially if I wanted to do something with some young ladies. Nice for a slumber party away from home!

Just got back from a girls trip and this hotel was great! Clean rooms and comfy beds. Great location. The bartenders at the lobby bar are great!

Freddie was friendly and great. We really enjoyed our stay and will be back!! Thank you Staypineapple and staff!

My friend and I decided to book three nights at this hotel for our girls trip and we couldn’t be happier. The customer service was great and both Cass and Marshay were very sweet and helpful. The rooms were a bit on the smaller side but the amazing view made up for it, the area was very safe even at night with lots of restaurants and things to do all around. The hotel was beautiful and very clean. Overall, very happy with our experience and would definitely book again.

Great location, comfortable rooms and wonderful employees. We had a wonderful stay at the Staypineapple. The beds are super comfortable. The water filling station in the lobby was super convenient. The staff went above and beyond and even decorated the room for my daughter's birthday! We had a wonderful time and would stay here again.

I had the pleasure of staying at Staypineapple this past weekend for my brother's bachelor party. There was a group of about 15 of us that come and went during the course of the weekend. First off, the staff was very friendly and accommodating throughout the course of our stay. We all liked the little amenities like the free drink pass, water and coffee stations. Location-wise, it was the best possible area to stay and you were within 10-15 minutes of most of the biggest attractions. I plan on staying there again the next time I'm in Chicago.

Great, friendly staff that went above and beyond for my nephew's birthday

The staff go above and beyond at Staypineapple! The concierge at the check in desk was friendly and welcoming. I went to Chicago with a friend to celebrate my birthday and the staff had cupcakes and a birthday card in the room for me. The location was perfect, so many destinations downtown were walkable and we utilized the valet parking which was convenient and reasonably priced. I would definitely stay here again!