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Whimstay: Your New Go-To for Last-Minute Getaways

I have a confession: I haven’t been super happy with Airbnb lately. The platform was my go-to for cute, affordable vacation rentals a couple of years ago. I love “boutique” experiences, and it’s so easy to find one-of-a-kind getaways on the platform–even ones that allow Atlas to come with us. But since they’ve started bumping up all those extra fees, the platform has become less and less affordable. Which is why I was so intrigued to learn about Whimstay

If you haven’t heard of Whimstay, it’s like Airbnb for last-minute vacations. Now, you don’t have to wait until the last second to book, but the closer you are to the date of your stay (<30 days), the better the deals get. But even looking well ahead, Whimstay’s prices seem to come out ahead compared to Airbnb and other booking sites. They have an average 22% discount and $234 in savings per trip. I’ll take that any day!

Infograph from whimstay
Perks from Whimstay website

So, obviously, when Whimstay reached out to ask if I’d be interested in giving their services a whirl, I said yes. If this was really as good as it sounded, I needed to know about it, and I wanted you to know about it, too!

Spoiler: it was fantastic. And if you’re looking for a last-minute Valentine’s getaway or a good resource for other spontaneous trips in 2024, you’ll want to save their website.

How Does Whimstay Work?

Whimstay header
Whimstay website

Whimstay works with property managers from all over North America to connect them with people needing spur-of-the-moment accommodations. It works well for both parties because the travelers get great deals, and the property managers have a seamless way to fill empty nights. Some rentals even allow same-day bookings, so you can quite literally travel on a whim.

The platform is geared toward budget-conscious travelers who still want a nice experience, and by giving these last-minute rates, more luxurious accommodations become much more accessible! It also provides additional savings through low fees, so you’ll always come out ahead. And the closer to the date you’re booking, the better the deal. They also tell you exactly how much you save on each rental compared to the full price. I really liked that transparency.

Featured rentals from Whimstay website

Last but not least, Whimstay only works with professional property managers. So you won’t be sorting through listings for people’s spare bedrooms or wondering when the space was last cleaned. Whimstay’s site says, “This ensures that the properties listed on our platform are clean, consistent with descriptions, and managed with expertise and the highest service standards.”

Note: Currently, the platform only has hosts in North America (Canada, USA, and Mexico), so you can’t use it overseas. But I’ll definitely be keeping an eye out in case they decide to add those options someday.

Full Review of My Whimstay Experience

The Booking Process was Simple

If you’ve ever booked a hotel or vacation rental online, you’ll have no problem navigating Whimstay’s user-friendly website. You can check out their featured deals right on the home page or insert your search parameters if you have something specific already in mind. Just enter your desired destination, dates, and guests (don’t forget to switch on the pet-friendly filter, if applicable), and the search engine will bring up your results.

Whimstay search bar

Once the results are pulled up, you can fine-tune your selection based on price, features and amenities, house rules, etc.

Since we were checking things out over a weekend, I chose to keep things close to home and search for Whimstays in Virginia. I found a great list of properties, all within a super-reasonable price range. And again, these were all entire homes, guest houses, condos, etc.

I spent a decent bit of time looking through results for research purposes, but you could easily hop on and book a stay within 5 minutes if you wanted to.

I ended up booking us for a stay at the Legacy Inn, a historic home in Luray, VA, that’s been transformed into a series of suites. It wasn’t quite a “B&B” or a hotel, but it had elements of both. I loved the cozy look of the property and how each suite had a fun theme.

All in all, we saved $63 on our 2-night stay through Whimstay (versus booking directly through the Legacy Inn), which I loved! Also, the cleaning fee was only $20, and taxes were $23. Compared to your average hotel, that’s not necessarily “great.” (Although, in some cases, that’s still a steal!) But compared to Airbnb, that’s phenomenal. My last 3-day Airbnb booking included a $68 cleaning fee, a $64 service fee, and $31 in taxes.

The only negative is that the site works much better on the computer than on mobile. My results kept relocating me to California for some reason, so I’d have to scroll back to the East Coast to see my results. But other than that, it worked well on mobile, too.

The Communication from Whimstay and the Legacy Inn was Quick and Professional

I immediately got a booking confirmation in my email from Whimstay that had all my reservation details and the contact information for the property manager.

Confirmation email from Whimstay

One minute later, I got an automated email from the Legacy Inn confirming my reservation, asking if I had any questions, and sending us the rental agreement and check-in forms. Now, this was a little more intense than just booking an Airbnb, but it definitely felt more professional. I don’t know if this is standard across Whimstay, but I’m sure that going through this process helps with the quality control of guests and ensures that the property stays in good shape.

Once I filed the paperwork online, I got immediate confirmation from the Legacy Inn, and they followed up two days before with check-in instructions, parking details, and a direct phone number.

While there, we ran into an issue with our keyless access code, so I emailed the Legacy Inn for help (there was no staff on site, which felt odd but made sense since it was a vacation rental), and Emily responded within 5 minutes.

Our Stay was Enjoyable!

The Cash & Carter Suite at Legacy Inn

We ended up having a wonderful last-minute weekend in Luray, Virginia. Now, you may have picked up on the fact that we don’t usually spend much time at our hotel when we travel. But since it was winter and we’d had a long week, Daniel and I spent quite a bit of time just chilling in our suite, and it was great! It was perfect for some relaxing reading, a little bit of Nintendo Switch, and lots of hot tea.

As I mentioned, this historic home was renovated into a series of themed suites. So each guest has their own bedroom and bathroom, but there were some shared living spaces, including a well-stocked lobby (with a coffee bar, tea, water, and fresh muffins), a big front porch with chairs and a swing, and the “Fitzgerald Living Room.” Unfortunately, we could not access the Living Room with our code, but we were pretty content to chill in our suite. That was the only negative I had about our stay.

Legacy Inn lobby

We stayed in the Cash and Carter suite, named for and themed after Johnny Cash and June Carter. It was decorated with guitars on the wall and even had a record player and vinyl of the duo. The bathroom was surprisingly large, and I was so happy to see that it actually had a counter! (Don’t even get me started on how much I hate pedestal sinks when I’m trying to do my makeup.) I also loved how cozy it was with the fireplace, two comfy chairs, and an oriental rug over the wood floors.

Large bathroom in the Cash & Carter Suite

The space had a few other thoughtful touches, like a Keurig with mugs and coffee pods, a mini fridge, a large wardrobe, bedside tables with USB charging ports, and a desk with a lamp.

All in all, it was super cute, and I would definitely go back for another stay there. It was less than 5 minutes from the Luray Caverns and downtown, so the location was perfect.


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Closing Thoughts on Whimstay

I’m not typically a spontaneous traveler, but a good part of that is because finding a spur-of-the-moment stay can be stressful or expensive. But now that I know about Whimstay, I may be looking closer at a lot more last-minute flights, knowing I can easily find a place to stay, too. I’m seeing some fantastic potential with this tool for spontaneous getaways to Canada or Mexico.

And for all of you out there looking for a good last-second Valentine’s Day getaway this weekend, be sure to check out Whimstay! You may just find the perfect little luxury spot without the price tag!

So what do you think? Have you tried Whimstay before, or will you give it a whirl this year? Let me know in the comments below! I love hearing from my readers and value your input and questions!

If you found this post helpful, please do me a quick favor and like and share it with your friends so they can save money this year, too! And, of course, if you’re not already subscribed to the blog, please join before you go! It’s free, and you get a couple of freebies for signing up!

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I hope you’ll be back soon for more helpful travel tips, itineraries, gear recommendations, and more so you can always have the perfect trip! Until then, take care, and happy travels!


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