Okay, okay. You may have a lot of questions, and I have some answers…

I needed a last minute hotel that was pet friendly, and thus I came upon StayPineapple. It’s in the South End and while I had a wonderful stay, there are definitely things that I wish were different. But let’s start with that BURNING question you have. (I know you have it).

Is it a swinger hotel?

Why is that even a question, you ask? Because if you didn’t know… upside-down pineapples are widely recognized symbol for swingers or people open to consensual non-monogamy. Right-side up pineapples are not and typically a symbol of warmth, friendliness, and generosity. Pineapple stay has RIGHT-SIDE-UP Pineapples! Get it right, people.

Dog Friendly x10!

So, I did bring my dog and she seemed to have a blast. Yes, even my DOG loved the naked experience (i.e. the bed sheets). Do you see that little smirk? Aww! Yes, this is Tess, my 12 year old Coonhound-mix.

The hotel is also conveniently located between a veterinary clinic, animal rescue and pet boutique! Quite the pet friendly area, wouldn’t you say!

This hotel is super dog friendly, if you go on their website (linked below) you’ll instantly know! They do have a fee and offer pup amenities for a special price as well. Taken straight from their website, Pup Amenities include:

• A special Staypineapple dog bed for use during your stay
• Staypineapple treats; we like to think of it as afternoon delights for your dog
• A collapsible water bowl that’s yours to keep
• Walk-friendly waste bags in a yellow holder to show your Pineapple pride for many walks to come
• Access to our Pet Wellness Program: includes a free trial of Zoundz, a sound therapy app to keep your pup zen, and VEG ER for Pets services, offering emergency vet care located near almost every Staypineapple hotel for those “uh-oh” or “oh no” moments.

You can find out more here.

There are always going to be those hotels that say they’re dog friendly, but when it comes down to it…they’re more like “dog neutral.” So if I haven’t convinced you yet…

• 2025 Bronze Medal Winner for Best Pet-Friendly Getaway in The Seattle Times Best in the PNW
• 2025 Listed as one of the Best Pet-Friendly Hotels in Newsweek Readers’ Choice Awards
• 2024 Most Pet-Friendly Hotel Brand in Good Housekeeping’s Family Travel Awards
• 2024 Winners of Silver & Bronze Medals for Best Pet-Friendly Getaways in The Seattle Times Best in the PNW Awards
• 2024 Listed as one of the 20+ Best Dog-Friendly Hotels in the U.S. by Parade
• 2024 Listed as one of the 15 Best Pet-Friendly Hotel Chains in America by Reader’s Digest
• 2023 Ranked #1 in BringFido.com’s list of Top Dog-Friendly Hotel Chains
• 2023 Winners of Gold & Silver Medals for Best Pet-Friendly Getaways in The Seattle Times Best in the PNW Awards
• 2023 Listed as one of the Best Pet-Friendly Hotels by Forbes

And if I STILL haven’t convinced you… well, I don’t know what else to tell you at this point LOL!

Amenities:

Considering the hotel was so convenient and within walking distance of many local stores, restaurant and big attraction in the South End Boston area, it was very moderately priced ($60-70/night), whereas most in the area around over $100/night. So I would’ve assumed they had little to no amenities, but I was so wrong!

I only stayed for a few days, so I didn’t need much, but one that I LOVED was the free coffee/tea. Yes, that’s right! So many hotels and even cruises have drinks in the rooms, but if you drink it- you’ll be charged. With Staypineapple, they give you unlimited in-room coffee and tea (plus creamers). If you need more of anything, you can always go to the front desk to ask.

They also have a SmartTV in your room, wifi, a complimentary reusable water bottle (which is in your room when you arrive, next to the Keurig), a free welcome drink, bikes to explore the city, a water bar to fill up your water bottle in the main lobby and signature pineapple treats from 3:30-6:30pm daily. So I’d say they have quite a lot!

Decor:

The decor of this place was cute! Pineapples and yellow/green everywhere 🙂 I don’t have much to say, but I hope the photos speak for themselves!

Parking:

I loved the hotel experience as a whole, but the one thing I wished was different was the parking. The Boston location, at least, had no parking available on site. There are metered parking spots (with a 2-hour limit and no allowed parking between 6-8am unless you have a residential permit) 2 hour parking directly outside of the hotel and other than that, a few garages in the area. You can also use SpotHero or another parking reservation online service.

I ended up parking my car in a parking lot about 0.3 miles away. It was around $50-60 but I wasn’t allowed to come in and out. Honestly, this area is super walkable, so it wasn’t really a problem and since my last stay in Boston, parking is a nightmare, so I walked pretty much everywhere, but if I had wanted to go further or explore more- I could definitely see it being an inconvenience. During this trip, I had only stayed 2 nights and one of those says was during a major snowstorm so I just visited restaurants, really. Last time I had come to Boston, I visited the Boston Commons (Freedom Trail), two museums- Isabella Gardener and the Museum of Fine Arts , the aquarium plus some restaurants/cafes- so I’m sure that would have been more inconvenient if I didn’t have my car. (But would it have because some of those parking spots were like $20 or more!?)

Fees/Not Included:

They do have a $50 deposit fee, but that should drop off after you leave. If it doesn’t, reach out to the hotel directly and they should be able to fix it.

Many hotels do offer a continental breakfast and unfortunately the PineappleStay does not. They do have the Trophy Room, an American restaurant, connected to the hotel, but it’s not free.

Do I recommend the PineappleStay?

I do! I thought it was a great place to be for a lower price in the area. The staff were nice and knowledgeable about the area, or at least could point me in the right direction. My room was right next to the elevators/staircase so I could hear people coming and going, but I wouldn’t say that it was “loud” or obnoxious. The hotel was also in a very convenient spot. Would I go here again? Probably, yes. Especially if I had my dog! When I don’t bring my pup, I usually stay with a friend so…there’s my incentive haha! But yes, I thought it was a lovely hotel, offered quite a few amenities and had a lovely clientele. It may not be the best for more conservative folks though 😉

– Sho

~Founder of Backroad Butterflies ~

Cheers Friends & Travelers! ✈️

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