Penny Weight Hotel
About Penny Weight Hotel
Unleash Your Inner Artist at 155 Portland, Hilton Pennyweight Hotel: Boston's Premier Paint Nite Destination!
Looking for the ultimate night out, a unique date night, or a something different to do in Downtown Boston? Discover 155 Portland, the signature restaurant and bar within the stylish Hilton Pennyweight Hotel! By day, it's a modern culinary hub, transitioning seamlessly into a classy and high-end cocktail and wine bar by night.
We're thrilled to partner with Paint Nite to bring you unforgettable paint and sip experiences in this vibrant space. Sip on expertly crafted cocktails and explore our curated selection of beer and fine wines while you unleash your creativity. Located in the heart of the city, our venue is easily accessible by subway North Station and Haymarket station, and just a stone's throw from iconic landmarks like TD Garden. In warmer months, enjoy our expansive outdoor patio with comfortable seating and mood lighting – the perfect spot to savor your drinks.
Upcoming Paint Nite Events at Penny Weight Hotel
Artists Who Host Here
What Guests Are Saying
The Pennyweight Hotel was a solid value for us during a quick two night stay in Boston. Even though the street itself can feel a little empty, the location is quite well-situated with easy walks to many North End historical sites like Old North Church and Faneuil Hall and I was able to smoothly get to the Charles River Esplanade one morning for a nice run. The location has great access to North Station and a ride to Fenway is no problem because the T is right there. Easy! The parking was straightforward and the valets friendly and attentive; the cost per night reasonable for the city. We brought our dog, too, and that was no hassle (Red Dog Pet Resort & Spa is just around the corner–very convenient for day care if you plan ahead!) We did not utilize the breakfast or bar area. Our room was compact–expected in a center city environment–but comfortable. There wasn't a lot of space in our room for work though I saw guests doing so at lobby tables during our visit. I read a comment about the size of the refrigerator and that's strange to me because it's basically the size of any small hotel room mini-fridge; it held a to-go pack of beer from Night Shift Brewing nearby at Lovejoy Wharf just fine. There was a little wear and tear to the room, though, which was surprising since the hotel seems recently remodeled. For example, several bars in the bathroom were nearly detached and the handheld shower head was not operable. These seem like easy fixes. I would definitely stay at the Pennyweight again.
My stay at the Pennyweight Hotel was outstanding from start to finish. The room was absolutely immaculate, clean, comfortable, and well-maintained. The level of service throughout our stay was exceptional. I would especially like to recognize Shared, the manager, for going above and beyond. During the second leg of our trip, when we were planning to visit Cape Cod, Shared took the time to provide wonderful recommendations on places to see and things to do. His local knowledge helped make our trip even more enjoyable. The hotel also had a centralized location which made it very easy to walk anywhere in boston
Dear Management, I would like to express my sincere appreciation for the outstanding hospitality my guest, Elizabeth Strickland, and I received during our stay at The Pennyweight Hotel in Boston from June 29 through July 2, 2026 (Confirmation #3461122350). From the moment we arrived until our departure, every member of your team made us feel genuinely welcome and valued. I would especially like to recognize Ashley and Edward at the front desk. They were consistently friendly, professional, and accommodating, always greeting us with a smile and making sure our needs were met promptly. A special thank you also goes to Tyrone, Account Manager, and Katland, Supervisor, for their exceptional customer service and commitment to ensuring we had a wonderful stay. Their attention to detail and dedication to guest satisfaction did not go unnoticed. Finally, I would like to commend Hansen, our valet. He provided excellent service and offered outstanding recommendations for restaurants in the area, which helped make our visit to Boston even more enjoyable. It is employees like these who make a hotel truly memorable. Their professionalism, warmth, and commitment to exceptional service reflect very positively on The Pennyweight Hotel. Because of this outstanding experience, I will gladly recommend your hotel to my friends and family, and I look forward to staying with you again on my next visit to Boston. Please extend my sincere thanks and appreciation to Ashley, Edward, Tyrone, Katland, Hansen, and the rest of your outstanding staff. Sincerely, Rich Cohen
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Book the whole room at Penny Weight Hotel
Birthdays, team offsites, bachelorette parties. You pick the painting, we bring the artist and the supplies, the venue handles food and drinks.
Reach Out to Penny Weight Hotel
Messages go straight to the venue's inbox — Paint Nite keeps a copy so we can help if it's about an event.
Paint Nite at Penny Weight Hotel — FAQ
None. Your artist walks the whole room through the painting stroke by stroke over about two hours, and everyone leaves with a finished canvas. Most guests have never painted before.
Parking varies by night in Boston — check the venue's website or give them a call before you head out.
Most venues keep food and drink service running during the event — ordered from and paid to the venue, separate from your seat price.
Doors open 30 minutes before the painting starts. Come early, grab your seat and order a drink — the artist starts on time.
Yes — Penny Weight Hotel has a wheelchair-accessible entrance. If you have specific seating needs, contact the venue ahead of the event and they'll set you up.