You're walking down Milk Street, the salt air from the Casco Bay hitting you right in the face, and then you see it. This massive, imposing brick fortress. It doesn't look like a Marriott or a Hilton. It shouldn't. The Portland Regency Hotel & Spa Portland is actually the old Milk Street Armory, built back in 1895 for the Maine National Guard. Honestly, if these walls could talk, they’d probably bark orders at you.
Most people visiting Maine's largest city get sucked into the shiny, new-build hotels popping up along the Fore Street waterfront. They're fine, I guess. But they lack the soul of a place that survived the transition from a military storehouse to a 1980s centerpiece of urban renewal. When you stay at the Portland Regency Hotel & Spa Portland, you’re basically sleeping inside a piece of neo-Romanesque history. It’s got that heavy masonry, those arched windows, and a vibe that feels like "old money" without being snobbish about it.
It’s kind of wild to think that soldiers used to drill where guests now sip local IPAs.
What Actually Sets the Portland Regency Hotel & Spa Portland Apart?
It’s the location. Period. You are tucked into the cobblestone heart of the Old Port. You step out the front door and you’re thirty seconds away from the best oysters of your life at Eventide or a weirdly expensive flannel shirt at a boutique. But the hotel itself is a bit of a labyrinth. Because it’s a converted armory, no two rooms are really identical. You might get a cozy nook with a sloped ceiling or a sprawling suite that feels like a captain's quarters.
The architects back in the day—Frederick Thompson was the guy—weren't thinking about "guest flow." They were thinking about defense. That gives the hotel a quirky, sturdy personality. You’ve got these thick walls that provide some of the best soundproofing in the city. In a neighborhood known for loud bars and late-night revelry, that’s a massive win.
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The Spa: Not Just a Marketing Gimmick
Most "hotel spas" are just a dark room with a massage table and a scented candle. The Regency is different. They’ve dedicated a huge chunk of the lower level to a full-service wellness center. It’s arguably one of the better spots in the city for a deep-tissue massage, especially if you’ve spent the day hiking around Bradbury Mountain or walking the Eastern Promenade.
They use a lot of local touches. Think sea salt scrubs and Maine-inspired treatments. It’s also home to a pretty decent fitness center, though honestly, most people are just there for the steam room and the jacuzzi after a long day of eating their way through the city.
Eating and Drinking at the Armory
Let’s talk about the Armory Lounge. It is dark. It is moody. It is exactly what a bar in a coastal Maine city should be. While everyone else is fighting for a stool at the trendy cocktail bars down the street, locals actually hide out here. It’s got that classic tavern feel—leather chairs, dark wood, and a fireplace that actually feels necessary about nine months out of the year.
The food is solid, standard New England fare. You're going to see a lobster roll. You're going to see clam chowder. Is it the most "innovative" food in Portland? No. Portland is a world-class food city with James Beard winners on every corner. But for a reliable, quiet meal when you don't want to deal with a two-hour waitlist at Honey Paw? It’s perfect.
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- The breakfast situation: It’s served in the Eighteen95 restaurant. It’s a bit formal.
- The coffee: Better than your average hotel swill, but seriously, go to Tandem or Bard Coffee if you’re a caffeine snob.
- The service: It’s "Maine friendly." Not fake-corporate-nice. Just real people who actually know the city.
What Most People Get Wrong About Staying Here
Some travelers show up expecting a cookie-cutter modern luxury experience with glass elevators and minimalist furniture. If that’s you, you’ll be disappointed. This is a historic property. The elevators are a bit slow. The hallways wind around in strange ways. Some people call it "dated," but I think that’s a misunderstanding of the brand. It’s "classic."
There’s also the parking situation. Like everywhere in the Old Port, parking is a nightmare. The hotel offers valet, which is basically a requirement unless you want to spend your entire vacation circling the block or feeding a meter every two hours. Factor that into your budget. It’s not a secret fee, but it catches people off guard.
A Note on the "Vibe"
If you’re looking for a party hotel, this isn't it. The Portland Regency Hotel & Spa Portland leans into a more sophisticated, quiet atmosphere. It’s popular with couples on weekend getaways and business travelers who are tired of the Marriott lifestyle. You’ll see people reading actual physical newspapers in the lobby. It’s that kind of place.
The Specifics You Need to Know
The hotel has about 95 rooms. That’s the "Goldilocks" zone—big enough to have full amenities, small enough that the staff remembers your face. If you can, try to snag a room on the higher floors. Some of them have views that peek out over the rooftops of the Old Port toward the harbor. Seeing the fog roll in over the brick buildings from your window is a very specific Portland mood that you just don't get at the highway-side hotels.
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They also handle a lot of weddings. If you’re visiting on a Saturday in October, expect to see a lot of bridesmaids. The Atlantic Ballroom is a big draw for locals because of that historic architecture. It’s one of the few places in town that doesn’t feel like a generic conference center.
Real Talk: The Cost
It’s not the cheapest stay in town, but it’s far from the most expensive. You’re paying for the footprint. In the height of summer (July and August), prices in Portland go absolutely insane. You might see rates triple compared to February. If you’re on a budget but still want the Regency experience, come in the "shoulder season." May or October are spectacular. The air is crisp, the crowds are thinner, and you can actually get a table at the bars.
Actionable Steps for Your Visit
If you’ve decided to book a stay at the Portland Regency Hotel & Spa Portland, don’t just sit in your room. Portland is a city that rewards the curious.
- Book the Spa early. Do not wait until you arrive. The locals know about this spa and they book it out, especially on weekends.
- Request a "Superior" room. The standard rooms are fine, but the superior ones often have those cool architectural quirks—like exposed brick—that remind you you’re in an 1890s armory.
- Walk to the waterfront. You are literally two blocks from the ferries. Take the mail boat run around Casco Bay for a few bucks. It’s the best "tour" in the city and it’s not a tourist trap.
- The Armory Lounge for a nightcap. Even if you aren't staying at the hotel, go into the bar. Order a local Maine beer (Allagash is the classic, but try whatever Bissell Brothers or Maine Beer Co. tap they have) and just soak in the atmosphere.
- Skip the hotel breakfast once. While their breakfast is good, you are a five-minute walk from The Standard Baking Co. Get a morning bun. It will change your life.
The Portland Regency Hotel & Spa Portland is a bit of an outlier. It’s a hotel that refused to change its DNA to match modern trends, and in a city that’s rapidly gentrifying and modernizing, that stubbornness is its greatest strength. It feels like Portland. A little rugged, very historic, and surprisingly comfortable once you get inside.
Check the seasonal packages before you book. They often bundle spa credits or dining vouchers that make the "Old Port" price tag a lot easier to swallow. If you want a stay that feels like you've actually visited Maine—rather than just a generic hotel room—this is the spot.