Half Priced Hotel Rooms if you Share Your Room with a Stranger, Plus Enter Day 8 of the 12 Days of Giveaways

Please note that I receive compensation for many links on this blog. American Express and other banks are advertising partners of this site. Read my Advertiser Disclosure policy to learn more.

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!

Editorial Note: The opinions expressed here are mine and not provided, reviewed or endorsed by any bank, card issuer, or other company including (but not limited to) American Express unless otherwise stated. Comments made in response to posts are not provided or commissioned, and they have not been reviewed or endorsed by any bank. It is not the responsibility of any advertiser to make sure that questions are answered.
Unauthorized use and/or duplication of the material on this site without express and written permission from this blog’s author and/or owner is strictly prohibited.

  1. Kenya F

    I definitely would not use hotel room sharing with a complete stranger. There’s just way to creepy and unsafe to me. Nope..no way!

  2. JP

    I might use it if they screened participants somehow – otherwise it seems like a great opportunity to be assaulted and/or robbed by a stranger.

  3. Jennifer

    I will not be participating in room sharing with a complete stranger. No way!

  4. Mike

    I could see this being useful for the type of individuals who like to couch surf, but no thanks for me.

  5. Denise L

    I would never book a hotel room to share with a stranger. I will be interested to see if Winston Club ever makes it out of the startup mode.

  6. iamalighthouse

    Um nope! No way booking a hotel with a random person!! 🙂

  7. Eddie Shih

    I don’t think I would ever want to share a room with an unknown person. It’s just too risky.

  8. Stacy

    No room sharing for me! But I’m old too 🙂

  9. Katie

    No, I don’t think I would use this service either….Share a room with a stranger? It is way too uncomfortable and risky.

  10. Steve

    I’ve stayed in plenty of hostel dorm rooms and airbnbs, but one-on-one hotel room sharing still sounds like a terrible idea.

  11. Mary Whitcomb

    Sharing with a stranger is not for me.

  12. Nancy

    Too weird and creepy and for me!

  13. Christina

    I would never do that!

  14. Michael H.(oldfox)

    I definitely would not use this hotel room sharing service. What….with a complete stranger? I love my privacy. Guess that is why I am still single.

  15. AannaT

    A hostel is one thing: lots of folks sharing a “public” room. Sharing a private room with a stranger, though? No, thanks! Bad combination of too much privacy and too much togetherness.

  16. Tiffany B.

    This sounds very similar to cabin sharing to avoid the single supplement on cruise ships. I would be concerned about safety.

  17. Cathy Krasnianski

    Having read so many horror stories about hostels, I can’t imagine ever sharing a private hotel room with a total stranger. No way!

  18. Jen

    It seems like they verify people, to whatever extent that is, and also pair same genders. It might catch on and if it becomes popular it wouldn’t seem so creepy.

  19. r hirsch

    i’d do it. why not? by and large, people are kind (it’s just you never read about kind people!).

  20. Swisspotluck

    I don’t think I would do it. If it was that important to save costs and I didn’t mind sharing a room, I would just stay in a hostel.

  21. Ricky Wolfe

    Very intriguing! Kind of like a higher end version of a hostel. Not sure it would be for me, but cool concept

  22. Marilyn B

    Not for me. Many years ago, when I was in my 20’s, I shared a room twice on bicycle tours – but that was a group tour with others in the group, and it was mostly geared towards singles anyway. Didn’t really enjoy that part of the experience, even though it was with like minded individuals, it was still uncomfortable but at least it wasn’t risky because we had tour leaders, etc. More like being in a hostel. But I would never share a private room with a complete stranger – the savings is not worth the risk to me.

  23. J.

    No sharing.

  24. Rich

    No way !!!!
    I don’t even like sharing a hotel room with a friend!!!

  25. dot cahill

    strange and scary

  26. nbdona

    my partner snores

  27. Paul

    Nope. Not worth it to share.

Leave a reply

Your email address will not be published. Required fields are marked *