Brandon Asks: Looking for a Hotel Near Fenway Park While the Red Sox are in Town

“Brandon asks” is a Reader Q&A series where we take real questions from real people and do our best to provide helpful unbiased information on navigating the points & miles space.

This week’s question comes from Karen who asks:

“Can you suggest a hotel near Fenway Park with reasonable pricing? I’m planning to visit Boston June 7th – 10th and go to a couple Red Sox games. Hotel rooms near the park look expensive for these dates so I’m motivated to consider signing up for one credit card to help take the edge off but I’m new to this points & miles stuff so if it’s too complicated I’d probably just pay cash and stay further away from the park to save money.”


Robert: Thanks for the question, Karen! I live in the Boston area so although I don’t stay in Boston hotels often I know the area around Fenway Park well. It’s a great city and the energy in the air when the Red Sox have a home game is incredible. You’re going to have a great time – even if you’re rooting for the visiting team.

This is a very “targeted” travel goal. I like that we have some time to generate the points needed, if points hotels are indeed the best option. But in general, we’d recommend gradually building point balances in flexible travel rewards programs so that when you have a need to travel you can do so deeply discounted without needing to suddenly earns some points.

Karen is new to this game and likely to give up if this gets complicated so we’ll have a rule like the Somali pirate in Captain Philips: “No tricks, Irish”.

That means no manufactured spending, no signing up for small business credit cards, no high min spend cards, etc. We want to keep this as simple as possible.

The first thing I did when I heard this question was spot check a couple of chain hotels near the park. Not necessarily because I think they’re the best option – I’d just like to get an idea of the going rates this time of year when the Red Sox are home.

First I checked the Sheraton Boston Hotel. It’s a short walk from the park, a safe/clean known commodity, and also near the desirable Back Bay neighborhood full of shopping and dining options. It checks in a whopping $538/nt. Ouch!

The nearby Hilton Back Bay goes for $351/nt.

If you look at the price of the Sheraton the next weekend (when the Red Sox *aren’t* in town) the price drops from $538/nt to $276/nt. Still pricey for what you get, but notice how the price when you pay with points stays the same irrespective of the cash price of the hotel. I’ll use this trend to your advantage when formulating a strategy for your visit.

Sam: Hi Karen, and thanks for the question. I’ll try to keep up with Robert here–being a Boston local he’s really going to get to the heart of the issue and give you the best local advice. But I can definitely add a bit here and there.  I’ll preface my answer with a little bit about my bias: I’m located on the west coast and I’m not a big fan of hotel points. That’s not to say I don’t collect some, but I think they’re not always the best solution.

With that said, it isn’t much help to recommend a hotel that’s not RIGHT near Fenway for a trip such as this.  I like to call this a ‘Suspension of the Rules,’ type situation.  My basic rule with hotels is that as the amount of time you’re in a city increases the number of places you want to see likely increases as well. You can expand where you search to stay anywhere in that area and still spend roughly the same amount of time traveling to see everything on your list.

In your case, you’re going to Boston to watch multiple games at Fenway, and staying as close to that focal point represents the best possible location for the relatively short trip you’re taking.  The hotels Robert recommends above know the game–when the Red Sox are playing they’re in a prime location. When the Sox aren’t in town they’re discounting their rooms in response to that.

The reason I’d stick with chain hotels, and specifically one of the two properties Robert pulled ties into Robert’s last point above, the room rate in points doesn’t fluctuate.  Robert’s picked a hotel (Sheraton) with a high cash price but a relatively low point price.  With a situation like that you’re going to be able to leverage an abnormally weak dollar against an abnormally strong hotel point.

I’m not going to recommend you stay anywhere but the Sheraton. This question has actually been a tough one to answer, because there’s a clear choice, but the why is something I’m struggling with explaining concisely.

For a full 3 night stay you’ll need 36,000 Starpoints vs. 210,000 Hilton Hhonors points.  36,000 vs 210,000 might seem like an easy choice–Starpoints and the Sheraton all the way. But those points aren’t worth identical amounts.   I’d ballpark (see what I did there?) the value of a Starpoint at about 4x the value of a HHonors point. For the sake of a quick discussion I’ll use current offers for the credit cards of each brand as an explanation why I value one at 4x the other:

The bonus is 4x the number of points, the earning is 3x. This is a quick and dirty way for someone with no prior experience with either program to compare the points. Nothing under the X is important so don’t read it.

So you’re looking at a 4x higher value currency in Starpoints. That helps you compare apples to apples a bit: 36,000 Starpoints are roughly equal to 144,000 Hilton Honors points. Again, this is really just to show you the reason I’m recommending the Sheraton. This kind of analysis is done near instantaneously if you’re already in the points/miles sphere and know these programs.

Since you’re just starting out Karen I hope I didn’t lose you with the above, because I haven’t even touched the second part of your question; how to pay for this hotel with a single credit card. I have a pretty good idea what to recommend, but I’m going to pass it back to Robert to see what he’s thinking, and if he agrees the Sheraton is the place to be, and to see if he thinks he can do this with 1 card as well.


Robert: Yeah, I hope we don’t lose her either.

I really do think that staying near the ballpark is the way to go for this trip, for two reasons. First, she’s going to the game 2 nights out of 3 she’s here. Second, because Fenway Park is uniquely situated in a great part of the great city of Boston. It’s an area you absolutely want to be in. You don’t get that in most cities.

Here at Milenomics we’re always more interested in the methods than specific solutions. If we share our methods with one another we learn to be more self-sufficient. So here are a couple of tools I’d use for a search like this.

If you search for Hotels on Google Maps it shows you paid rates for specific dates displayed on a map. Quite useful!

The next tool I’d use is Hotel Hustle. It consolidates points hotel rates on a map for the specific dates you’re looking for. It’s very useful for quickly surfacing up points hotels in general and shows you the cash rate, the points rate, and even the cash + points rate (if applicable) for quick comparison.

I don’t mean to latch on to this Sheraton too much, but my goodness: It’s a great points redemption.

Notice a couple of things in the rate page below. First, you can pay with all points or with cash + points. This could be useful if you can’t quite generate 36,000 Starpoints in time for the stay. Second, the $547 rate is a *prepaid* rate (non-refundable) and doesn’t include tax.

If we look at refundable rates things are even more expensive. A total of $2,249 for 3 nights in a Sheraton? Wild. But for 36,000 Starpoints that’s a whopping 6.24 cents per point of value. I think we can see why some people do crazy things to remain loyal to Starwood properties, and great lengths to gin up Starpoints.

There may be some funky independent boutique hotel or AirBnB I’m missing. But I’m liking this redemption.


Sam: I love what Robert said above about being more interested in the methods than the solution.  I think it’s also really interesting to see how everyone has their own ‘style’ in searching for travel. I use Hotel Hustle as well, but that Google search is really slick, new to me and definitely something I’ll be using from now on.  

And I love the Cash + Points option for something like this hotel, the value there is really great as well. But I really do fear I’m going to overly complicate this discussion right here and totally lose you Karen:

All of the pricing Robert lists above is ‘retail’ price. We’re Milenomics…we never pay retail.  For this hotel, in this situation there’s a really easy solution that gets the rate for this exact room down to about $270 a night:

Buy the points.

Yep. Almost never makes sense, almost universally a terrible deal. But I didn’t call this a “Suspension of the Rules” booking for nothing.  Take a look at the current SPG promo on buying the points outright:

I’ve done this before myself when there were really high cash prices and really low SPG point costs. I just didn’t have the time to earn these the old fashioned way… 

Seems crazy, right? That they would list this room at a price and then allow *anyone* to buy enough points for the room for $409, and $125 a night?

There’s no special credit card needed, you just buy the points for $409.50, and book the room for $125.89 a night.  This also significantly increases the number of cards I can now recommend you to apply for and get. The 28,000 SPG sign up (+3000 for min. spend) is just not enough points to book the room on points alone. But the current buy points promo has me thinking of some really off the wall card ideas for you.

Robert’s right; I like to find hidden boutique hotels, or AirBnBs, but not today. Any chance that I was going to recommend an AirBnB, or a cheaper hotel kind of gets thrown out the window when the exact hotel we want you to stay at is now more than 50% off  the retail price and competitive with even the low end properties out there.

Robert: Wow, that is slick Sam. Didn’t see that one coming, and I even saw the Starwood 35% off points promo in my inbox today. But absolutely, it’s right their on their website. Just go to -> Buy Starpoints and it takes you the page where you can buy Starpoints:

The per-night cost (if Karen were to buy those 18,000 Starpoints at 35% off the going rate) is $262.39/nt including taxes. That’s a savings of 65% off the refundable rate.

All Karen would have to do is create an SPG account, buy the 18,000 Starpoints, and book the room. How easy is that?

I always like to think of what could go wrong with an approach before diving in head first. This one looks pretty sound, but let’s work through it.

One scenario that’s not great is if Karen decides to cancel the trip. Her cash + points reservation is refundable up until 3 days before arrival (just like a regular cash reservation is) but she’d get refunded in cash + points, leaving her with 18,000 Starpoints. If she’s not a regular traveler this might not be ideal. Sure she could always transfer them to an airline, often a uniquely good option with Starwood, but that’s obviously more complicated than just getting a refund and moving on with your life.

On the flip side, one risk of delaying booking is that the points redemption options at this hotel could disappear. I think of that as a risk associated with earning the required Starpoints, or most of them, through a credit card signup.

One scenario could be that Karen signs up for a new credit card with a signup bonus roughly worth $500 towards any travel, buys the 18,000 Starpoints with that (which helps towards min spend), then “erases” a little over $500 of the $787.18 total cost. But I think that’s getting too complicated. The Startpoints purchase isn’t going to code as travel and she’s bound to get frustrated [rightfully] even with the simplest of travel rewards credit cards.

I’m going to cut to the chase (no bank pun intended) and recommend she signup for an AmEx Starwood Preferred Guest credit card.

The AmEx SPG card has a signup bonus that bounces around between 25,000 and 30,000 points (if you’re lucky). Sometimes it goes up to 35,000 points (if you’re really lucky). The standard signup bonus for the card at the moment is 25,000 Starpoints.

Now, I know we said “No tricks, Irish” but I think we can get a 30,000 point offer to appear.

See, AmEx does like to play tricks and depending on how you arrive at their site they show different offers. Try doing a Google search for “spg amex”, then follow the first non-Ad link:

What I see when I do that in an Incognito web browser (or a browser with no AmEx cookies) is a better offer, for 30,000 Starpoints:

We don’t get anything from this card application. We’re recommending this because it is a solid offer, not because we get paid when you apply for this card.

As you can see from the offer if you spend $3,000 on the card you’ll get 30,000 Starpoints. The $95 annual fee is waived the first year.

So Karen would:

  1. Create an SPG account at (and take note of her SPG account number)
  2. Sign up for an AmEx SPG credit card (and enter her new SPG account number on the application so they know where to credit the points)
  3. Once the card arrives, spend $3,000 on it
  4. At the first statement close after spending $3,000 she’d have at minimum 33,000 Starpoints (3,000 from the spend)
  5. She could use those 33,000 Starpoints to pay for the room (and buy some additional Starpoints if needed to top off her SPG balance)
  6. Enjoy the game!


Sam: 30,000 SPG through an incognito link. Really nice find Robert, I hadn’t heard of that offer yet. I am able to see it on my end doing the same google search (incognito).  I think that card is a really good fit for you Karen. I could recommend something else that earns really good Cash back, but Robert’s incognito link is the better move. He’s also covered the potential pitfalls of each path (buying the points vs. earning them via signup bonus).  I’ll use my closing time to just go over some basic information Karen should keep in mind.

The card above gets you really close to the points you need for the room.  You’re getting a $2200 $787 room with the points from this sign up and about $125. By using the 33,000 points Robert outlines above for two room nights and booking the last night as Cash ($125) + points you’ll end up with about 3,000 Starpoints left over. Back of the envelope I’ll call that ~$60 in points.

I would caution Karen from thinking the kind of results we were able to make happen above can be repeated with Starpoints anywhere/everywhere. This time they were the right tool for the job. Next time they might not be. Karen probably won’t want to keep using that SPG Amex card for daily spend.  But again, I’m biased against hotel points and I don’t know your travel pattern well enough to say that with complete certainty.

Robert and I both spent about an hour each going back and forth on this piece, but someone who’s new to all of this would have easily spent much more time learning what we just went over.  That investment in time is not insignificant, but can be extremely lucrative. We’ve shown you how to attack a hotel booking, and how to apply for a card that gets you pretty close to your hotel goal for this trip. We also put a pretty strong argument up for a deeply discounted cash booking through buying Starpoints.

One thing is for sure: You’ll want to start reading more Milenomics and trying to put together your own best system.

Now you just need to score some game tickets…. paging Vinh.

Did we get it right? Join the conversation by leaving a comment below. And drop us an email or hit us up on Twitter @Milenomics if you’d got a question we can tackle.

About the author

– Written by Robert Dwyer, contributor at Milenomics. Connect with me on Twitter @RobertDwyer


    1. Great point ABC.

      Since she’s new to all of this I’m guessing we scared her off with this wall of text and ideas and she’ll just buy the points and call it a day. We’ll hopefully hear back and can update with what she actually went with.

  1. I love how you guys are explaining the methods and not specific solutions – I’m learning new strategies I can apply to my own travel scenarios. Extremely helpful!

  2. Thank you for the time and effort clearly put into this post and the Brandon Asks posts. I check the points blogs regularly and these posts have stood out to me as valuable and helpful. I have a family of 5. I’ve been collecting points since 2014. I don’t MS so I don’t have a huge stash of points and I’m always looking for how to put the points I have to the best use to create great memories for my family. I appreciate the helpful information on how to put the points I have to the best use. Thank you and I hope you keep putting out content like this!

    1. I just checked again and I too see 25,000 now. 🙁
      You never know with these AmEx incognito deals though, maybe try mobile devices/other browsers/connected to a VPN in another part of the country?
      Good luck.

    2. I saw your comment this morning and it wasn’t working for me either. But I just tried again (Chrome, incognito) and it is working for me right now using Robert’s instructions in this post.

  3. Hey guys,

    Great job. As a former Bostonian (in fact I used to live kitty corner to Fenway Park on Jersey St / Peterborough), I would actually look at recommending a different hotel. You guys are in love with the Sheraton Back Bay, but I would see a lot of potential value in the Holiday Inn Brookline. That hotel is about a 10 minutes walk from the park, in the direction opposite to the craziness. Also the hotel is a category 6 (35K IHG points). The cash rates on that hotel are also much more reasonable than the Sheraton should you need to go that way. That being said, I think that the IHG program is great in specific situations, and that includes doing an IHG Accelerate promotion. I think that with an IHG Accelerate promotion that is favorable, the earning of 70K points can come at a very low cost. This should not be ignored.

    The Sheraton is charging a very healthy premium for being in Back Bay in the summer. The Holiday Inn is in Brookline and really not far from the “action” and their value really depends on which “Boston” Brandon is interested in. I know that my stepbrother came to visit me when the Jays were in town and he didnt care to go anywhere but the games. Assuming Brandon has a //similar laser focus, he is paying a large premium to stay at the Sheraton over the Holiday Inn Brookline. That premium is in not only the amount of points, but also in the fact that everything in the hotel and in Back Bay is going to come with a premium over Brookline.

    The Holiday Inn can be a redemption for an annual free night on the $49 fee IHG credit card (though I would argue that this is probably poor value). A new sign up of the IHG credit card gets you at least 70K, which is 2 nights (similar to the SPG card) noted above.

    As mentioned above, I like the Holiday Inn as an alternate option, only because it is slightly closer to the park, in a nice but quieter neighbourhood. And I think that IHG points are very easy to earn with an IHG Accelerate promotion.

    My personal bias is against SPG hotels only because I find it surprisingly difficult to earn those points and those 36K points could have value in the range of $800 or so.

    The Holiday Inn Brookline wont be nearly as nice as the Sheraton, but I think there is more likelihood of getting a

    1. Buying IHG points outright at $0.007 each would mean the Holiday Inn Brookline would be $245. Not ideal to buy straight out, but that puts a cap on that price.

      With an IHG Accelerate promo for Q1 2018, I bet 70K IHG points would be easy to achieve with 2 or 3 nights, especially if Brandon hasnt had any Accelerate promotions before.

      The Sheraton will be a nicer hotel than the Holiday Inn, for sure.

      I think there is value in evaluating the Holiday Inn as an alternate option.

      1. Al: I really appreciate this detailed response. I think the option you outline is a good one. The strategies you’re recommending seem to mirror the ones in the post as well. I’ll make sure to forward your comment to Karen for her to consider it as well.

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