As (crazy) busy on-the-go professionals and digital workers of tomorrow…it’s more critical than ever to set time aside and escape our bubbles, immersing ourselves in fresh environments outside the hysteria of relentless progress.

We’ve got to remember to build ourselves as much as our products, projects, and profiles!

Something I highly recommend to people who haven’t delved yet…is VRBO and AirBnB. They’re very similar in how they work – you can rent a furnished property for a set amount of time – but here’s the differences in brief:

  • Vacation Rentals By Owner tends to offer more upscale properties, while with AirBnB there’s a wide selection from as low as $50 a night to the more expensive and luxurious.
  • I prefer the mobile version of AirBnB, primarily because it loads faster! If you’re using wifi and an inexpensive laptop/phone, navigating VRBO can be frustrating.
  • The key is going with groups and splitting costs. So, with 5 people spending $70-120 a night you can rent a roomy 5-bedroom oceanfront wonderland. No, really.

Life’s short. If you can pull together this kind of trip, I can’t speak highly enough about it. Get some friends to join the crusade and do something wild. Or hey, gather your small startup team for a road trip-style mastermind retreat.

As an example, eight friends and I recently returned from Breckenridge, Colorado, where we split the cost of this amazing 2BR with a loft. Got the price-per-person down from roughly $550 to $70 a night.

Breckenridge VRBO

Hot tub, pool, less than two blocks from town and the ski resort’s main lift…it was actually quite nice. For my troupe and I the pull is skiing and snowboarding.

That’s us in the header image of this article. I’m the guy on the far left.

Sure, if it were up to me we’d talk shop and get heavy into business chatter all day, but my work retreat group just aren’t into it. Gives me a chance to really escape my clients, my startups, new software product going live, and yeah, you know exactly what I’m talking about.

Instead, it was about skiing and enjoying the beauty of Breckenridge mostly from the slopes. Here’s a pic on that VRBO property’s page that shows peaks 7 & 8 in the distance from Blue River Plaza.

VRBO Breckenridge CO

So, I’ve got a challenge to just put out there on the net and see if by chance anyone goes for it.

And yes, this is more designed around folks that live on the western side of the U.S. who can reach each destination within one driving day. If you have to fly to Montana and rent a car the costs increase dramatically, but hey, maybe that’s no big deal for you and your squad.

You just needed someone to suggest a brilliant scheme.

  • 4 Friends, 4 Cabins, in 4 States, in 14 Days.
  • 1 day of travel and 2 nights for each location.
  • From Montana, to Idaho, to Oregon, and then cap it off in Washington.
  • I split the example ideas up, alternating between two from VRBO and two from AirBnB.
  • These may be completely booked as you read this, but there’s plenty of other options.


Cabin #1: Montana – Whitefish Lakefront Cabin

Montana Cabin Vacation Rental

Source LinkWhitefish Lake VRBO Cabin

Right? Doesn’t matter the time of year, whether the pristine lake’s encircled in green or flakey white snow-covered trees. Your ensemble at your side, surrounding peak-lavished scenery will help you escape the mayhem without breaking the bank. A private dock and beach, the hot tub, and all that outdoor space to stretch your wings…a great beginning.

Here’s a little snippet from their info section:

Glacier National Park’s wonders are about a 30-mile drive from this home – an easy day trip. Check out the Jewel Basin for hiking options a little closer to home, or take this rental’s own kayak out on Whitefish Lake for some summer fun. Whitefish Mountain’s ski slopes, renowned for their pristine powder, are an 11-mile drive around the lake – on a clear day, you can catch a glimpse of them from this home’s balcony.

It’s about an 8 hour drive to the next destination, so you’ll want to get up early and on the road. Try to get to the next cabin by 5-6pm same day.


Cabin #2: Idaho – Fireweed Cabin McCall

Idaho Vacation Rental

Source LinkIdaho AirBnB Vacation Rental Near McCall City

The selection in terms of Idaho cabins is growing more astounding by the year, but right now one I’ve definitely got on my bucket list is the Fireweed Cabin close to downtown McCall city – a neat resort town up against the southern shore of Payette Lake.

Because it’s an “all-season tourist destination for outdoor recreation” it doesn’t really matter which season you choose for your visit – cozy inside year round.

Vacation Rental Idaho

You’ll love this cabin and Spring Mountain Ranch because of the simplicity, quietness, outdoor living area, clubhouse pool, hot tub, steam room and workout room. This is a cabin/second-home subdivision so typically you are one of the only persons there!

If you dig hiking and go in a warmer season, make sure to spend some time in nearby Ponderosa Park. I’m not kidding, I’ve had many ‘light bulbs’ go off while on trails just moving through the moment amongst nature’s splendor. How about you?

It’s another 7 to 8 hour drive from McCall city to Mt. Hood. Based on 200+ reviews, looks like a great place if you want amazing locally-sourced burgers for breakfast in McCall if you don’t plan on leaving till closer to noon, would be My Father’s Place (opens at 10:30 a.m.).


Cabin #3: Oregon – Mt. Hood Hideaway

Oregon Vacation Rental By Owner

Source LinkMt. Hood VRBO Luxury Cabin

Yes! Although be prepared for a bit of an elevation jump, this mountain jewel cabin comes with 3 beds, a loft and 2 baths. You’re within reach of world-class dining, shopping, and the renowned Timberline Lodge – often a networking extravaganza of ‘who’s who’ if you’re a social butterfly.

Tucked away in a quiet area, nestled into a hillside our beautiful mountain home is near 3 major ski resorts, hiking, biking, fishing, the sandy river, lakes, wildwood recreation and everything the mountain has to offer.

Oregon Vacation Rental Cabin

What really put this on my personal bucket list is the charming wood burning stove, and how homely (in the British sense) the cabin is designed. Hardwood floors, river rock floors in the 2 full bathrooms, of course a fully-equipped kitchen, and a relaxing rustic feel surrounded by forest.

See how amazing this is for the road trip-inclined? With four friends, at the current pricing I see, it would cost you about $35 a night to stay there. Peanuts!

It’s about rejuvenating yourself and your entrepreneurial spirit. With a group of friends the costs get way down there, yet you can live like millionaires and let loose…

This final cabin was suggested by a friend of mine who lives in the town nearby. As the crow flies, depending on traffic, it’s another 6-8 hours from Mt. Hood to Mt. Baker but this last location will be so worth it!


Cabin #4: Washington – Mt. Baker Twin Tree House

Vacation Rental Washington

Source LinkMt. Baker Treehouse AirBnB Rental

Located in Whatcom County, WA, this is a “rustic, clean, comfortable, cozy, pet-friendly, and classic cabin with a large hot tub, updated kitchen, and main bathroom.” You’re right by Mt. Baker Ski Resort, and about 30 or 40 minutes to downtown Bellingham.

If you don’t want to utilize the kitchen below, no problem, Bellingham is one of the most intense foodie cities on the West Coast. There’s over 20 amazing breweries and most of them sell food as good as their beers!

Should you be down for that kind of sudsy thing, check out Kulshan Brewing and Aslan Brewing.

Interior Washington Vacation Rental

Bellingham is an outdoor lover’s paradise, with little gem-cities like historic Fairhaven to the south and Birch Bay to north. A great place to cap off the trip and spend any extra time you have. It’s another town that you’ll love regardless of the season. Don’t be afraid to talk to locals. There’s tons of college kids from WWU, but the locals are so nice and will help you enjoy your time.

What do you think? Sound like an adventure you could pull off? Whether it is or not, I hope I’ve inspired you to book your first or next AirBnB or VRBO. Get out there. Immerse yourself in new different spaces and stir your entrepreneurial innovative soul.

Then, after you’ve reached Zen, leave a comment below and share a destination with me and other readers that really knocked your socks off.

Happy Trails!