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Most Short Term Rentals Are Managed. Very Few Are Optimized.

Most Short Term Rentals Are Managed. Very Few Are Optimized.

We help Wisconsin property owners turn average-performing rentals into high-performing assets through design, branding, and hands-on revenue strategy.

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Owning a Great Property Should Feel Like an Asset Not Another Job

Most STRs do not underperform because of demand. They underperform because of positioning, design, branding, and revenue strategy. That is where we come in. Clear Trail helps owners improve how their property looks, how it is marketed, how it is priced, and how it performs, without giving up owner control. This is better because it matches your premium positioning and works whether the visitor is self-managing, unhappy with current management, or still considering launching.

Cohosting

Why Is Clear Trail Different?

Block 1

We prioritize performance over occupancy

Most managers aim to fill nights. We focus on increasing the value of each booking through better positioning

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We don’t rely on “set it and forget it” pricing

Automated tools are common. Real results come from hands-on strategy and active revenue management.

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We treat your
property like a
unique asset

We build a custom approach around
your property

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You Stay In Control

You receive payouts directly. No hidden fees. No surprises.
your property

What Makes Us Different?

Design That Delivers

We’re not just managers — we’re experienced creators.
Ashley is a top STR designer. She will help you transform your space into a vacation destination guests rave about and return to year after year. No matter the style or setting, she designs each property to stand out and perform at a higher level.”

Advanced Marketing = More Bookings

We don’t just list your home — we launch it.
From SEO-rich listings and dynamic pricing to targeted ads and social media, we use modern marketing tools to reach more guests than the big platforms alone ever could.

Revenue Strategy That Is Actually Hands-On

Most companies call it revenue management when they mean software. We combine tools with active oversight, manual adjustments, and strategy tailored to your property.

100% Transparency & Owner Control

Unlike traditional property management companies, you stay in full control. Payouts go directly to you, and we invoice transparently at month end

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Who are we?

We’re not a volume-based property manager.

Clear Trail Properties was built by STR investors who saw most rentals are run on autopilot—standardized, hands-off, and average.

We partner with owners who want more. Every property is treated as a unique asset, with intentional design, positioning, marketing, and pricing.

Because today, performance comes down to one thing: execution.

That’s why we stay boutique, hands-on, and strategy-driven.

What is Co-hosting?


Co-hosting is a partnership model where you retain full ownership and control of your property while we handle the day-to-day operations of running it as a short-term or mid-term rental.


That includes everything from guest communication and pricing to cleaning coordination, maintenance oversight, and listing optimization—so your property performs at its highest level without the hands-on work.

  • We do all the heavy lifting
  • You receive direct payouts
  • We invoice only at the end of the month

No hidden fees. No locked-in contracts. Just real results.


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How we get your property launch-ready

We’ve developed a streamlined onboarding system to make things easy from day one:

  • Discovery Call – Let’s see if we’re the right fit
  • Home Evaluation + Design Guidance
  • Setup of Listings, Pricing, and Systems
  • Go Live – Start Hosting, Earning, and Relaxing

We’ll walk you through every step and handle the rest.


Who We Partner Best With?

Clear Trail is perfect for:

  • Owners already renting and ready for a more strategic approach
  • Owners frustrated with their current management company
  • Owners preparing to launch a vacation home the right way
  • Investors who want a more hands-off, higher-performing setup
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From Ashley:


If you care about how your property is positioned, how it performs, and how your guests experience it, we should talk. Clear Trail was built for owners who want more than average management. If that sounds like you, book an intro call and let’s see if we’re a fit.


Ashley Lang
Professional Cohost | Clear Trail Properties


Frequently Asked Questions

What makes Clear Trail Properites different from the big box managers like Vacasa?

Unlike big-box companies that treat your property as just another number, we provide personalized service with dedicated managers, custom cleaning checklists, and proactive communication. We're locally focused and accountable to our performance guarantee.

How much do you charge for cohosting?

Depends! We manage both mid-term rentals and short-term rentals in many different markets. The rate varies from 15-25% depending on your rental. We meet to discuss this in deep detail and then we give you a quote.

Do you require long-term contracts?

No long-term contracts required. We believe in earning your business through results, not binding agreements. You can terminate service with 60 days' notice.

What markets do you serve?

We currently serve select markets where we can maintain our high service standards. Contact us to see if your property location qualifies for our cohosting services.

How do you handle guest issues and emergencies?

We provide 24/7 support with local emergency contacts and immediate response protocols. Our team handles everything from minor guest requests to urgent maintenance issues, keeping you informed throughout.

What cleaning and maintenance services do you provide?

We coordinate professional cleaning with custom checklists for each property, conduct regular maintenance inspections, and have trusted local contractors for repairs. All services are quality-guaranteed.

How do you optimize pricing and bookings?

Yes! We use dynamic pricing tools combined with local market knowledge to maximize your revenue. This includes seasonal adjustments, event-based pricing, and competitive analysis to keep your rates optimal.

How do I get started?

Schedule an intro call with us today! Let's see if we are a good fit.

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