Hotel Review: The Liberty, Boston

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I headed to Boston for my first PAX last week and, having waited way too long to book, took the opportunity to stay at The Liberty, a Luxury Collection Hotel within the Starwood brand, and as good a place to launch our hotel coverage as any.


The Liberty is probably the coolest and one of the most beautiful hotels in Boston. It’s plethora of restaurants and bars make it feel like a Vegas resort in miniature, and it’s dog-friendly. On the other hand, its location isn’t ideal, it’s pricey, its best amenities will cost you additional $$$, and walking through a party to get to your room at the end of the day isn’t for everyone.

History and Location

Built in 1851, the architecturally stunning Charles Street Jail (they really don’t make ‘em like they used to) would eventually become The Liberty Hotel. Located at the Charles River edge of Boston’s Beacon Hill neighborhood, The Liberty is off the beaten path, but very much within walking distance of both historic and touristy Boston.



I stayed in two different rooms at The Liberty, but more on that later. The rooms are beautifully appointed with touches informed by the building’s history that go just far enough, and beautiful city views contingent upon which room you’re in.

Expect great water pressure for a hotel in the walk in shower, along with a comfortable separate tub and Molton Brown toiletries.

Rates start under $200 according to some quick searches, but my room(s) were 3X that due to the amazingly busy time Boston was experiencing.

Dining and Amenities

There are a lot of people eating and drinking at The Liberty who are not guests of the hotel on any given night. The food and booze are pricey but great, but the real draw is the stunning lobby, which reserves the catwalk (as in the one from the prison) for guests to work on during the day and drink from at night.

Dining includes Clink., part of the new SPG Cravings program, which offers 10% off for SPG members.


The Liberty, thankfully, offers 24-hour room service, though be prepared to pay up. Room service isn’t known for being cheap, but a sandwich and a pasta dish with no additions rang up at $73, before additional tipping.

The hotel also leans heavily into nightly events, with everything from live music to fashion shows to puppy play dates happening at any given time. Speaking of, they’re dog-friendly, and I wasn’t charged the $100 dog deposit.

Don’t expect a rooftop heated pool here though.

What Went Wrong

I wasn’t too surprised to get a “come back tomorrow” after asking about a room upgrade for my Gold status, given I checked in around 11pm. Walking into a room to see it was clearly a lesser tier than the one I booked was a different story.


To greatly summarize what was a comedy of errors that I really didn’t have time to sit at the hotel to deal with, it appears that the hotel put me in a handicap room when I checked in due to low inventory at that time of night. They had a note about my room being “moved” in their system, which never happened, and also had my third night entered as a separate reservation, which it wasn’t.

I checked in late Wednesday night, and didn’t make it into the right room until Friday around lunchtime. I called the hotel yesterday to ask for a make good and they readily issued me 5000 Starpoints.


Maximizing Points

Whether you have Starwood status through your Amex Platinum or you got it the hard way, enjoy your bonus point return, take your welcome gift as points, and decline housekeeping to get even more points.

It might be intuitive to book your Starwood stay with your Starwood Preferred Guest Amex, but no, use your Chase Sapphire Reserve for maximum return.


This was also a great reminder for me about how important it is to confirm you’re signed up for all of a hotel brand’s promotions prior to booking. I got around 12,000 Starpoints for this 3-night stay, not counting the 5000 point make good, or the Ultimate Rewards points.