Winston Club is a startup company that offers hotel rooms at a steep discount.

Although they are just getting started and will be adding more cities as they go, if you are looking for a room in the following cities you might be able to snag a great deal:

• Seattle
• San Francisco
• Los Angeles
• Miami
• Chicago
• New York City


Prices are half of what you’d normally pay and are at name-brand hotels, but there is one catch – you have to share your room with a stranger.

How does it work?

Per their website, you sign up as a member and create a trip. This involves choosing the city where you’d be staying, and selecting a hotel from the available options. When another traveler has dates/preferences that coincide with yours, the company sends you an email and you can then choose to accept. Once the stay is completed, you will have ended up paying just half of what you normally would for your hotel room.


Geared towards those who are comfortable with the “sharing economy”, it could be a way to make a new friend or simply have overlapping travel schedules where you happen to share the same hotel room.


According to Winston Club’s website, safety and security are important to them so there are multiple levels of verification checks done on members. There is also a focus on same-gender pairings.

Checking out the random date of February 17, 2017 for Los Angeles, I was immediately given two properties to choose from. There was the Kimpton Hotel Palomar, and The Hotel Wilshire. Both displayed typical rates with the Kimpton at $240, and a note that upon accepting a roommate there would be a refund of $139 (half, including taxes and fees).


I checked Kimpton’s website as well, to see what kind of rates there were for those dates. The advance purchase rate was $281, the AAA rate was $290, and the best available rate was $330.


Winston Club’s Terms of Use  says that bookings have specially negotiated rates, and confirmed that they are prepaid rates. Note that even though the rate looks like a much better deal with Winston Club, there is also a Facilitation Fee for each booking that will be tacked on. I don’t see the fee amount listed anywhere but when new members sign up they are surely informed of the amount (maybe a reader can report back if they find out the fee). Maybe $25?

The name brand hotels that Winston Club focuses on have free Wifi and free breakfast. One perk I think is neat is that on their website it says that Winston Club will offer you a free credit at local breakfast locations if the hotel doesn’t include it –

If breakfast isn’t included, Winston Club offers you a free credit at some of our favorite local breakfast locations.

I still have questions though.

When I pull up the calendar for any two months, why are Monday, Tuesday, and Wednesday nights blocked out? I would think those would naturally be the days where entrepreneurs needing a quick trip might use this sharing service to help keep their costs low (unless a company is paying for their trip).


As they are pretty new, I’m guessing that Winston Club simply doesn’t have enough negotiated deals with hotels yet so they cannot offer full calendar dates much like they don’t have hotels in all cities yet.

It sounds like they have thought of some of the potential stopping blocks that could make this service tricky, but I am so curious about how the loyalty points work. Most miles & points hobbyists will agree that it is great when everyone around the dinner table pays you cash and then you can use your credit card to pay for the entire meal (and earn the points!).

If you are the first to make the reservation with Winston Club, a roomie accepts to stay with you and pay half, do you get to keep the loyalty points? What about loyalty benefits, do they extend to both people in the booking as they would with a typical hotel reservation? I skimmed their Terms of Use and didn’t come up with anything conclusive. It could be that you are not eligible to receive points for the stay at all, depending on what was negotiated between the hotel chain and the Club.

Today is also Day 8 of the 12 Days of Giveaways.


For those just joining, click here for full contest details.

To enter today’s contest, leave a comment about hotel room sharing. Would you use it? Have you already signed up? Think it is weird and creepy? I don’t think I would use this service myself but can see how it could be an excellent way for people in college or just wanting to save some money to really cut down on costs.

Today’s contest ends at 9pm PT December 20, 2016.

Good luck!