The Best Towns to Own a Short-Term Rental

In today’s competitive, oversaturated short-term rental market, it can be tricky to find the perfect location that checks all the boxes for owning and operating a five-star rental property. Play your cards right and a short-term rental has the potential to be more than a side project, but a profitable investment that does more for you than merely breaking even, can provide a reliable flow of cash that’s stable enough to survive market trends, economic fluctuations, and more.  

A lucrative rental property isn’t solely about finding a dreamy location (but don’t discount that!), the secret sauce lies in discovering a market with untapped potential. Think: a scenic destination, available property with great earning potential, and a high-quality modern cabin that you can transform into a successful, rentable retreat. 

After digging into the data and daydreaming about the many amazing places one could go to getaway — and yes, of course, build a dream DEN cabin — we found five of the best towns across the US for owning an outdoor-centric short-term rental property. 

From a coastal hamlet in Maine to secluded hideouts in the Midwest and creative hubs within an hour drive from downtown Manhattan, here are the five best towns to build your DEN and become a short-term rental property owner.

Southwest Harbor, Maine

A tiny seaside town on Mount Desert Island, Southwest Harbor, Maine is only minutes away from famed Acadia National Park. As its name implies, the harbor is a popular destination for world-class boaters and watercraft owners and builders who drop anchor in its waters, eager to explore the charming downtown, top-notch eateries, and of course, the sprawling trails of Acadia. Since the winter climate renders this coastal hamlet an isolated and well, chilly, place to be, Southwest Harbor has lots of potential as a great short-term summer rental when visitors can enjoy everything the town has to offer, as well as the fall when leaf peepers come from all over the world to see coastal Maine’s changing colors.

Three Rivers, California

In a canyon filled with oak forest, rivers, and lake, Three Rivers, California sits in the foothills of the Sierra Nevada mountain range and is colloquially known as the “Gateway to the Sequoia-Kings Canyon”. Conveniently located halfway between San Francisco and Los Angeles, Three Rivers is attainable for folks in the city looking to book a vacation in a scenic destination that isn’t too crowded or overpriced. The short-term rental market trend company, AirDNA, found that Three Rivers is a location with a high demand for rental properties, which means its ripe for aspiring hosts looking for the perfect spot to build and rent a DEN.

Cold Springs, NY

A simple one-hour train ride or quick drive up the interstate gives urbanites easy access to the mountains, river, and picturesque landscape of New York’s much-loved Hudson Valley. This half-mile long town is situated on the banks of the Hudson River and has become a popular place for city dwellers to escape the crowded streets of Manhattan for a long weekend and a slower pace — that’s not just hearsay, statistics from a property management company show that the region generated $280 million from visitors who booked short-term rentals. So, if close proximity between the city and the mountains didn’t already convince you that a Hudson Valley town like Cold Springs is one of the best places to own a short-term rental, then we bet the numbers will.

Galena, Illinois 

A small town boasting big attractions, Galena, Illinois might not ring a bell to some, but in the Midwest, this little city has earned a reputation for weekenders who crave creature comforts and the restorative effects of being in nature. Don’t believe us? DEN Barnhouse builders and short-term rental owners of the Ten Mile Cabin in the woods of central Illinois prove that the area is an ideal place to put up your “Out of Office” message and unwind.  

Brookings, Oregon

Located on the state line in the southern terminus, Brookings is a gateway to some of Oregon’s most scenic (and famously warmest) coastline. Explore twelve miles of rugged shoreline along the Samuel H. Boardman Scenic Corridor or venture inland to see the towering redwoods,  not to mention the wild rivers and state parks that make this a veritable adventure hub. The outdoor recreation alone makes Brookings, Oregon an ideal city to invest in a short-term rental property — it’s not hard to imagine an A-Frame cabin tucked away beneath a canopy of trees in the redwood forest, or a small cabin with ocean views. However, there’s also a vibrant culture for the locavores who come for the food and drinks and a cozy stay in a modern cabin.