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Jessica Litras

Staypineapple South End Boston

Staypineapple South end Boston REVIEW

One of the most interesting, funky and fun hotels I’ve stayed at to date. Staypineapple is a unique collection of boutique hotels with locations in New York City, Chicago, San Francisco, Boston, Seattle, Portland and San Diego. Their vibe attracts a tribe of the young, young at heart, savvy travelers and seekers of something different. Staypineapple is described as a badass experience where all your wants and desires are met. That includes the hotel being dog-friendly! If you’re a dog mom or dad, you can bring along your pup as they highly encourage it and accommodate here at Staypineapple. More and more hotels are becoming dog-friendly and it’s about time! 

I had the pleasure in staying at the Staypineapple, a Delightful Hotel, in historic South End Boston. Let me start out by saying that South End is an awesome location to stay in the city, especially if you’re visiting for the first time. South End Boston is known as being a culinary hub with entrepreneurial restauranters and delectable cuisine. Victorian brownstone buildings, fine restaurants, thriving arts, several outdoor parks and famous streets like Tremont Street, Columbus Avenue and Massachusetts Avenue are some of the things you have to look forward to. 

Staypineapple South End Boston Review
JESSICA LITRAS

Staypineapple South End Boston

Staypineapple South End Boston Hotel Review

If you’re interested in visiting Boston and like the sounds of the South End Boston culture and offerings, then Staypineapple is a “wicked smaht” choice for you, especially if you’re looking for more of a budget-friendly hotel. Staying in cities can be quite an expensive experience between the hotel, restaurants, bars and activities. Staypineapple can help enhance your city experience through it’s laid-back vibes with authenticity and class.  

There are a few things that make Staypineapple special that are worth mentioning. They have sanitation protocols that help keep the environment safe, healthy, and super clean for all guests and pets. Being that the hotel is dog-friendly, the cleaning and sanitation are taken up a notch to make sure everyone is comfortable. This includes a zero contact guest experience with a mobile check-in feature, a Stayclean Staypineapple room seal to let you know they’ve sanitized the room before entering and certified team members that go through comprehensive training and education when it comes to sanitation as well as sanitizer stations available throughout the hotel. 

Generally, if you need anything at all during your stay, you can always approach the friendly staff at the front desk for assistance. 

One of my favorite features of the hotel is what they like to call “The Naked Experience.” 

They offer a cozy, fresh, cuddly and luxurious atmosphere with extremely large and comfortable beds, that you feel like you’re sleeping on a cloud. Cozy is my middle name, so this was right up my alley. 

Being dog-friendly in itself is a unique and appealing feature for dog lovers alike. Staypineapple encourages you to “bring your best friend with you” on your journey at Staypineapple. They even offer a Pineapple Pup Package with 50% off your daily pet fee when you book directly on staypineapple.com. Dog amenities include a Staypineapple dog bed, a treat tin in the main lobby, colorful water bowls in the room that are yours to keep, as well as a walk-friendly waste bag in a yellow holder to show off your Staypineapple pride when you go on walks with your dog. The coolest part is if you want to go out and explore areas of the city where you can’t take your dog, you can absolutely leave them in the room! It doesn’t really get more convenient than that. 

Dog-friendly hotel in Boston

How to Get There

Staypineapple South End Boston is located at 26 Chandler St, Boston, MA 02116 Lexington, MA 02421. The closest airport to the hotel is Boston Logan International and is only a 17 minute drive away. Ubers anf Lyfts are plentiful, so you won’t have a hard time getting one to and from the city. Budget car rental return and pick up at Boston Logan Airport are located at 15 Transportation Way, East Boston, MA. Drive to Logan Airport and follow signs for the Rental Car Center. After returning the car, customers may take the complimentary shuttle to the airport.

If you’re looking for directions from out of town, you can find the exact location here. 

The Room

The Staypineapple room is a lot of fun and has everything you need. There’s a plush king bed, large TV screen, cozy Staypineapple yellow robes, a coffee machine with branded mugs, a standup shower and an elegant yet laid-back atmosphere. I truly felt very comfortable in this room and slept great!

Hotel close to Boston Logan International
Staypineapple South End Boston Room
Staypineapple South End Boston Room beddings
Staypineapple South End Boston Review Room View
Staypineapple South End Boston Review Coffee
Staypineapple Boston Yellow Robe

Staypineapple South End Boston Amenities

Special amenities you have to look forward to during your stay include The Naked Experience featuring double duvet European-style bedding, cozy lightweight robes, dog-friendly, smoke-free, afternoon delights including coffee and signature pineapple cookie treats, pineapple quick bites and bevvies, in-room coffee and tea, unlimited bottled water and beach cruises. One of the most unique and active features includes their beach cruisers otherwise known as the official yellow and green Staypineapple bikes you can borrow and ride around town. It’s an excellent way to get in a workout and explore the city. There’s plenty to do within walking distance, but bikes make it all the more fun to get around. 

laid back hotel boston
Staypineapple South End Boston
Staypineapple South End Boston

My honest review of Staypineapple South End Boston

My experience at Staypineapple South End Boston was definitely a positive one. I’m used to staying at bit more high-end hotels and this one was super laid-back and fun. I love their pineapple theme and that dogs are welcomed here. I love the double duvet covers, one for me and one for Bubs. And I love the lightweight robes, the in-room coffee while getting ready and the fact that you can see the city street from your window for that classic South End feel. 

The hotel building itself definitely has an older feel to it. The ground floor feels a bit outdated and somewhat dusty from the constant traffic indoors and outdoors, but we got used to it pretty quickly. The hallways also had a somewhat musty smell to it, but not to the point where it was gross or overwhelming. The room itself was the cleanest and most immaculate part of the hotel which is most important. The hotel is great for more low-maintenance, laid-back, adventurous folks, and of course dog-lovers!

Overall, we had a great experience. I don’t think I would personally stay at another Staypineapple and that’s only because I prefer a bit more luxe vibes. 

Staypineapple South End Boston honest review

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Local Eats Week is officially here, and it’s the perfect excuse to explore the incredible restaurant scene right here in Plymouth, Massachusetts. 🍽️🍹  From cozy neighborhood favorites to elevated coastal dining, participating restaurants are offering 2- or 3-course prix fixe menus starting at just $20.  ✨ March 6–13, 2026  Participating restaurants include:
@carmelasrestaurant
@indieferm_brewing
@mammamiasrestaurants
@martinisplymouth
@mayflowerbrew
@mirbeauplymouth
@plymouthbaywinery
@sobol_duxbury
@sipat1620winebar
@thespeedwelltavern
@stuzzi.co
@threevrestaurant  Which restaurant are you trying first? 👀  #plymouthma #southshorema
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Local Eats Week is officially here, and it’s the perfect excuse to explore the incredible restaurant scene right here in Plymouth, Massachusetts. 🍽️🍹 From cozy neighborhood favorites to elevated coastal dining, participating restaurants are offering 2- or 3-course prix fixe menus starting at just $20. ✨ March 6–13, 2026 Participating restaurants include: @carmelasrestaurant @indieferm_brewing @mammamiasrestaurants @martinisplymouth @mayflowerbrew @mirbeauplymouth @plymouthbaywinery @sobol_duxbury @sipat1620winebar @thespeedwelltavern @stuzzi.co @threevrestaurant Which restaurant are you trying first? 👀 #plymouthma #southshorema
10 hours ago
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Welcome to my cozy, coastal life on the south shore of Massachusetts 🌊🤍 #southshorema #coastalliving #cozyliving
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Welcome to my cozy, coastal life on the south shore of Massachusetts 🌊🤍 #southshorema #coastalliving #cozyliving
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Stepping into my “it’s almost spring” era. 🌷✨  Moving to a coastal town at the tail end of fall was an interesting time because it was freezing within a week of being here. Meaning, we have yet to experience a true summer on the coast. Prepare to be sick of me because I don’t think I’ll ever shut up about living in such a beautiful place.  Home is where the ocean is.🌊  #plymouthma #southshorema #coastalliving
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Stepping into my “it’s almost spring” era. 🌷✨ Moving to a coastal town at the tail end of fall was an interesting time because it was freezing within a week of being here. Meaning, we have yet to experience a true summer on the coast. Prepare to be sick of me because I don’t think I’ll ever shut up about living in such a beautiful place. Home is where the ocean is.🌊 #plymouthma #southshorema #coastalliving
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If you’re interested in transforming your smile, I can’t recommend @plymouth_orthodontics enough. From day one, every visit has felt comfortable, effortless, and honestly fun. The team genuinely listens to your concerns, explains every step, and brings such a high level of expertise to the process. And yes, it’s completely painless.  Of course, I wanted a more aesthetic smile. But Invisalign isn’t just cosmetic. It’s about long-term dental health, proper alignment, improving your bite, preventing uneven wear, reducing strain on your jaw, and helping you avoid bigger (and more expensive) issues down the road.  And the technology is SO advanced. You get custom aligners made specifically for your teeth, fewer in-office visits, the ability to remove them to eat and brush, and tools to track your progress at home. I’m not going to lie…I fully geek out over this stuff and love that we have amazing options like this available to us.  If you’ve been putting it off, don’t! Future you will be very happy you started now.  Use my name when booking your consultation at Plymouth Orthodontics and you’ll get $250 off your treatment.  You’re welcome. 😌🦷✨  #plymouthma #southshoremass #southshorema
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If you’re interested in transforming your smile, I can’t recommend @plymouth_orthodontics enough. From day one, every visit has felt comfortable, effortless, and honestly fun. The team genuinely listens to your concerns, explains every step, and brings such a high level of expertise to the process. And yes, it’s completely painless. Of course, I wanted a more aesthetic smile. But Invisalign isn’t just cosmetic. It’s about long-term dental health, proper alignment, improving your bite, preventing uneven wear, reducing strain on your jaw, and helping you avoid bigger (and more expensive) issues down the road. And the technology is SO advanced. You get custom aligners made specifically for your teeth, fewer in-office visits, the ability to remove them to eat and brush, and tools to track your progress at home. I’m not going to lie…I fully geek out over this stuff and love that we have amazing options like this available to us. If you’ve been putting it off, don’t! Future you will be very happy you started now. Use my name when booking your consultation at Plymouth Orthodontics and you’ll get $250 off your treatment. You’re welcome. 😌🦷✨ #plymouthma #southshoremass #southshorema
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New England destinations worth visiting in the Spring. 🌷  After a record breaking blizzard in Massachusetts, we all need a little to look forward to. Here’s some of my favorite places:  📍Rockport, MA - THE quintessential New England coastal town. This is the number one place I tell people to go when they are visiting Boston and still want to see the coast. The shops, art scene and restaurants are phenomenal. We love staying at @addisonchoate.  📍Burlington, VT - The foodie town that everyone needs to visit at least once. Love the local cuisine, breweries, downtown energy and outdoor scene. We love staying at @essexresortspa.  📍Newport, RI - A stunning beach town to visit before the crowds hit. Love Newport for its mansions, outdoor hikes and events. The Oyster and Chowder Festival is a must! We love staying at @hotelvikingnewport.  📍North Conway, New Hampshire - My favorite area in New Hampshire with so many beautiful surrounding towns, parks and outdoor adventures. We love staying at @omnimountwashington.  📍Cape Cod, MA - Another gem in the spring since the crowds haven’t quite hit, yet there’s still so much to do between the historic landmarks, water activities, and outdoor dining. We love staying at @pelhamhospitality.  Who’s ready for spring travel?🌷  #newengland #newenglandliving #newenglandtravel
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New England destinations worth visiting in the Spring. 🌷 After a record breaking blizzard in Massachusetts, we all need a little to look forward to. Here’s some of my favorite places: 📍Rockport, MA - THE quintessential New England coastal town. This is the number one place I tell people to go when they are visiting Boston and still want to see the coast. The shops, art scene and restaurants are phenomenal. We love staying at @addisonchoate. 📍Burlington, VT - The foodie town that everyone needs to visit at least once. Love the local cuisine, breweries, downtown energy and outdoor scene. We love staying at @essexresortspa. 📍Newport, RI - A stunning beach town to visit before the crowds hit. Love Newport for its mansions, outdoor hikes and events. The Oyster and Chowder Festival is a must! We love staying at @hotelvikingnewport. 📍North Conway, New Hampshire - My favorite area in New Hampshire with so many beautiful surrounding towns, parks and outdoor adventures. We love staying at @omnimountwashington. 📍Cape Cod, MA - Another gem in the spring since the crowds haven’t quite hit, yet there’s still so much to do between the historic landmarks, water activities, and outdoor dining. We love staying at @pelhamhospitality. Who’s ready for spring travel?🌷 #newengland #newenglandliving #newenglandtravel
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Thank you Mr. Feeny for always reminding us what’s important in life. 🤍 #boymeetsworld
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Thank you Mr. Feeny for always reminding us what’s important in life. 🤍 #boymeetsworld
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