Here’s the Lucky Winner Who Will Receive $10,000 to Redo a Failed Vacation

See recent posts by Alisha Prakash

This one’s for all of you who have ever booked a hotel online, only to arrive at your accommodations to realize your expectations and reality don’t align. Perhaps that pool wasn’t as big (or blue) as it was advertised, or the beach was photoshopped to create a false illusion of serenity. Well, you aren’t alone. A staggering $6 billion is wasted every year on bad hotel stays, due to things like a lack of cleanliness, dated decor, unhelpful staff, and sky-high prices.

Though you can’t return a bad vacation, stepped in to help one lucky individual redo it. Earlier this year, we asked travelers to share their tale of a vacation gone awry for the chance to receive $10,000, plus our unparalleled expertise, to do-over their failed trip. After reading through 6,367 responses, we’ve chosen our lucky winner.

Cheryl K. embarked on a couples’ trip to the Caribbean. She picked a resort with butlers, and even paid for a swim-up suite. Upon entering, however, her dream vacation turned into a disaster. The room smelled like a “wet basement,” Cheryl recalls, but that was just the beginning. Black mold on the decor pillows and crawling ants on the bathroom counter soon followed. (Cheryl went to the gift shop and bought aromatherapy to kill the stench in the room as a temporary fix.) While Cheryl admits the beach was nice, she said, “As soon as we returned to the room, it was hell again.” 

Even worse, night number two brought mice to their room — not to mention, rude, unhelpful staff. Though Cheryl and her husband were moved to a different room — sans bad odor — no one came to restock the minibar, and their butler was nowhere to be found. 

But the nightmare doesn’t end there. Water seeped through the ceiling and into their new accommodations — a result of the room above using their Jacuzzi. After a lot of unhelpful responses from the hotel staff, the manager eventually came to apologize and offered them an upgrade, under the condition that signed a paper stating they wouldn’t tell anyone what had happened here. “I already knew I would never return,” Cheryl said. To top it off, Cheryl got ill from the food at the resort. “This was the worst trip I’ve ever taken in my life,” she said. 

Cheryl wasn’t the only one with horror stories to share. Some participants told tales of bedbugs, unpleasant sewer odors, sketchy stains, water leaks, lost reservations, and dead chipmunks in the toilet. Others spoke about being duped by a hotel’s misleading marketing (one family’s mountain view room was obstructed by power lines and an advertised “private balcony” was not so secluded). Mishaps of missing one’s own wedding due to a violent illness and how a sunrise bike down Maui’s Haleakala Volcano resulted in 56 stitches also made their way on the list.

Now, Cheryl will be heading back to the Caribbean for a second chance at her trip. Stay tuned as we reveal more details about her getaway, including where she’ll be going, the resort she’ll be staying at, and more. And don’t forget to check for honest reviews and undoctored photos of hotels to make sure you know exactly what you’re going to get before you check in!

All products are independently selected by our writers and editors. If you buy something through our links, Oyster may earn an affiliate commission.