Finding Unique Places to Stay While Traveling

I am definitely a rebellious traveler. Rebellious travelers avoid anything on the beaten path, especially corporate chains. For rebellious travelers, accommodations are more about the potential experience than the mattresses, sheets and towels. Most are frugal, not necessarily out of necessity, but because rebellious travelers have learned that the value of an experience has no correlation to its cost. This is exactly why one of the primary goals of a rebellious traveler is to find unique places to stay while traveling.

I became conscious of my travel rebelliousness several years ago on the islands of Maui and Kauai.

A business conference brought my then-husband and I to Maui where we were lavished with corporate perks, including a spacious beachfront hotel suite with a bathroom as big as my bedroom at home. My husband reveled in the luxuries and brought all of his employees in to marvel alongside him. I didn’t complain—the view was breathtaking, our suite was institutionally attractive, and we weren’t footing the bill—but, I was far from revelry.

Fast forward five days forward to a tiny studio on the North Shore of Kauai where I would relish a week of solitude and mind cleansing.

I couldn’t help but chuckle at the dichotomy in my accommodations—from a ginormous 5-star bathroom to a tiny outdoor shower next to an active pasture and lush rainforest. Now, here I reveled, especially when I discovered that the water was piping hot.

Since my first outdoor shower, I have slept in some unbelievable places—from retro motor inns to converted wheat mills to a room in a crumbling castle. Each one has gifted me an experience I would have missed had I slept within the corporate lines.

I hope to fuel the rebellion by sharing some of my best resources.

Unique Hotels, Motels & Inns

Rarely do I have to search further than these four websites to find unique hotels, motels, and bed and breakfast inns:

  • TripAdvisorHead straight for the “B&B & Inns” and “Specialty Lodging” tabs first, then shop the “Hotels” tab.
  • Bed and Breakfast—You’ll find a wide variety of inns here, all with the wonderful perk of breakfast.
  • Yelp—Type in the location you’re wandering in the upper right box, click the Search icon, then choose “Hotels and Travel” followed by “Highest Rated” and start moving down the list. Move past the corporate chains that are doing a fine job and look for the eclectic gems.
  • All The RoomsThis site claims to have access to “every room on the planet,” so you’d have to try hard not to find something cool here.

Vacation Rentals

I am a passionate cheerleader for the “sharing economy” team that was reborn during the recent recession. Not only are you likely save a sizable amount of cash because of much lower nightly rates as compared to hotels, but you’ll likely have access to a kitchen to help minimize your restaurant tab.

  • Airbnb—From hammocks to castles, this site is rife with fodder for awesome experiences.
  • TripAdvisor—Yep, they also have vacation rentals. Type in the location and look for the “Vacation Rental” tab.
  • VRBO—An acronym for “Vacation Rental by Owner,” this site is best for stays of at least one week.
  • Get My Boat—Yes, you can even be rocked to sleep by the gentle bobbing of someone else’s boat.


My stint as a Hostelling International volunteer cured me of a nasty hostel stereotype. I saw firsthand that they were not all filled with inebriated international students who missed the toilet by 12″. Hostels are like people—there are countless types, shapes and sizes—and it’s entirely wrong to slap them with a single label.

Some of the hostels I’ve stayed in were as cozy as home, while others were institutional. Regardless of their personal style, they will stretch your travel dollar far. I recommend poking around—and reading the reviews—on these two sites:

A Few More Tips

Here are a few more tips I’ve learned along the way:

  • Never pass up the opportunity to talk to a local, especially one that is familiar with the local tourist industry. They’ll often be able to point you the best of the unique.
  • Don’t forget to just Google Type in where you’re wandering and pertinent details about your trip theme (i.e., romance, hiking, cooking, girl’s weekend, etc.) and you’ll almost always be directed to just the place you’re looking for or someone who can help you find it. I’ve helped a fair amount of people myself!
  • If the independent booking site says the place you had your heart set on is fully booked, email or call it directly. More often than not, I’ve gotten just the room I wanted by being persistent.
  • Go with your gut…it’s usually right.

My Favorite Unique Places to Stay

Here are some my favorite unique places to stay while traveling: