Asheville to the Smokies — STR Advisory & Co-Hosting

Your Property. Your Call.
Our Expertise.

Most property owners don’t need someone to take over — they need a partner who actually knows what they’re doing. Hillside Stays brings industry-leading tools, proven workflows, and hands-on advisory support to owners across WNC and the Smokies who want results without giving up control.

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$280+Avg. Nightly Rate
73%Avg. Occupancy Rate
$1,200/moFrom $1,200/mo Flat Advisory Retainer
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Sound Familiar?

Owning a short-term rental shouldn’t feel like a second job.

Most property owners in the mountains bought their cabin as a retreat or investment — not a second job. But between guest messages at 11pm, chasing cleaners, juggling platforms, and trying to figure out pricing… that’s exactly what it becomes.

Hillside Stays was built for a different kind of owner. One who wants to be a great operator — but needs the right systems, tools, and advisor in their corner to do it. We don’t take over your property. We build the infrastructure behind it, teach you how it works, and work alongside you to run a smarter operation.

See How It Works
💸

OTA Fees Eating Your Margins

Airbnb and VRBO take 3–15% on every booking. We build you a direct booking channel so you keep more of what your property earns — and own your guest relationships.

🕐

No Time, No Systems

Without the right tools and workflows, every guest message and cleaning coordination falls on you. We build the systems that handle the routine — so your time goes toward decisions, not operations.

📉

Revenue Left Behind

Static pricing, weak listing copy, and no direct booking presence means you’re leaving real money on the table every month. We audit, advise, and build the infrastructure to fix that.

Luxury mountain cabin nestled in hardwood forest in Western North Carolina, managed by Hillside Stays
⚡ What We Build For You
The Hillside Stays System
Smoky Mountains & WNC · Every Advisory Partner Gets This
🌐Custom direct booking website on your own domain
🔍SEO strategy built to rank in local searches
📲Social media setup & content scheduling
🤖Fully automated guest journey & communications
📈Dynamic pricing reviewed daily by our team
Direct
Booking Website Built
$0
OTA Fees on Direct Bookings
Ranked
SEO-Optimized Listing
Auto
Fully Automated Guest Journey
What We Build

Every advisory partner gets a direct booking home base —
built for them.

Most operators list on Airbnb and stop there. We build the infrastructure behind your property — a custom direct booking website, SEO strategy, social media presence, and automated guest journey — so your revenue isn’t held hostage by OTA algorithms and fees.

Every owner we partner with gets this system built for them from day one: your own domain, your own brand, your own direct channel. It’s the difference between renting a listing and running a business.

“Every owner we work with gets the same foundation — a custom direct booking site, an optimized listing, and revenue infrastructure designed to compete on any platform and win off of them.”

While other operators are dependent on Airbnb, we’re building the system that makes you less dependent on it.

See exactly how our system works →
What We Do

Advisory partnership. Systems expertise.
Results you keep.

We build your systems, advise your strategy, and work alongside you to run a smarter, more profitable operation — while you stay in control of your property every step of the way.

Most Impactful

Direct Booking Infrastructure

We build your property a custom direct booking website, SEO strategy, social media presence, and automated guest journey — so you own a revenue channel that works outside the OTAs. Every owner we partner with gets this built in from day one.

  • Custom direct booking website on your own domain
  • SEO strategy built to rank in local search
  • Social media setup & content scheduling
  • Booking engine + automated guest communication workflows
  • OTA fee savings compound over time as direct bookings grow
▶ See how our direct booking system works →

Guest Communication Systems & Support

We build and configure your automated guest communication infrastructure — AI-assisted workflows trained on your property, voice, and house rules. You stay the host of record. We make sure every message that goes out is accurate, warm, and on-brand.

  • HostBuddy AI configured and trained on your property
  • Automated messaging sequences for every stage of the guest journey
  • Escalation support — we advise on edge cases, you respond
  • Check-in & checkout communication workflows
  • Review follow-up sequences built in
▶ See exactly how our system works →

Weekly Pricing Strategy & Advisory

Every week we analyze your calendar, local demand, competitor rates, and seasonal trends — and deliver a clear pricing recommendation. You review it, you implement it. You always know why your rates are what they are.

  • Weekly rate review & advisory report
  • Event & season surge pricing recommendations
  • AirDNA competitor market analysis
  • Multi-platform rate strategy (Airbnb, VRBO + direct)

Operations Consulting & Vendor Framework

We build your operational infrastructure — turnover checklists, vendor sourcing, supply standards, and maintenance workflows — and document everything so your property runs consistently without you managing every detail.

  • Turnover SOP & quality checklist development
  • Vendor sourcing recommendations — you hire & direct
  • Supply standards & restocking protocols
  • Maintenance workflow documentation

Advisory retainers start at $1,200/mo. Flat fee, scoped to your property and goals. No percentages. No hidden charges. Book a strategy call to find the right fit.

Book a Strategy Call
The Real Math

What OTA fees are silently
taking from your bottom line.

OTA commissions remove a meaningful chunk of each reservation; by moving bookings to your direct channel you avoid those commissions entirely. Using a $280 nightly and 73% occupancy as an example, avoiding a 15.5% OTA fee adds about $950/month (~$11,400/year) to owner revenue on that property; at 8% the uplift is ~$490/month (~$5,900/year).

  • Real uplift (same price, direct): Avoiding OTA commissions adds between $490–$950/month for a $280-night property at 73% occupancy, depending on the OTA.
  • Capture more (direct pricing): By moving guest-facing fees into the nightly rate on direct bookings you can keep that money as owner revenue while keeping guest costs similar.

Want to see what your property could earn with a direct booking channel? Book a strategy call.

Platform OTA Rate Monthly Avoided Annual Avoided
Airbnb 15.5% $950.46/mo $11,405/yr
VRBO 8% $490.56/mo $5,887/yr
Generic OTA 10% $613.20/mo $7,358/yr

Assumes $280/night and 73% occupancy; actual amounts depend on platform settings and account type.

The Hillside Stays Difference

Powered by AI.
Built for the mountains.

Most operators in this space are running on spreadsheets and gut instinct. We’ve built a professional-grade tech stack — AI-assisted communications, automated workflows, dynamic pricing tools, and direct booking infrastructure — that we deploy for every owner we work with.

The technology handles the speed and consistency. We handle the strategy, the judgment, and the relationships. The result: a smarter operation, better guest experiences, and a revenue channel you own — not one you rent from Airbnb.

Learn More
<5min Avg. guest response time
Weekly Pricing review, advisor-delivered
$1,200/mo From $1,200/mo flat advisory retainer
Typical Co-Host
Hillside Stays
Guest Response Time
Hours
Under 5 min (AI-assisted)
Pricing Updates
Set it and forget it
Weekly advisor review
Direct Booking Channel
None
Built & optimized for you
Owner Reporting
Monthly PDF
Real-time dashboard
Systems & Automation
Manual workflows
Full stack deployed & configured
Who’s in Control
The co-host
You — always
Your Time Spent
Still too much
Focused on decisions, not operations
The Process

From strategy call
to a fully operating system.

Getting started is straightforward. We build your full system from day one — including the direct booking infrastructure most operators skip.

01

Strategy Call & Property Assessment

We start with a paid 60-minute strategy session ($150, credited toward your first month). We review your property, your current setup, your market, and your goals — and walk away with a clear picture of what your operation needs and whether we’re the right fit.

02

Advisory Agreement & Onboarding

We formalize the partnership with a straightforward advisory services agreement. You stay in full control of your listing accounts — we request co-host access where needed to configure tools on your behalf.

03

Infrastructure Build-Out

We deploy your full tech stack — PriceLabs, HostBuddy, Breezeway, Hospitable, and your direct booking website. We document every system, walk you through how it works, and hand you an operation you actually understand.

04

You Go Live — With Us in Your Corner

Your listing is live, your systems are running, and you’re in the driver’s seat. We deliver weekly pricing recommendations, provide ongoing advisory support, and are available when you need us — but you operate the property.

05

Review, Iterate, Grow

Each month you receive a performance report. We review it together, adjust the strategy where needed, and keep building toward a stronger direct booking share. Your retainer is invoiced monthly — flat fee, no surprises.

Everything included.
One flat retainer.

✓

Direct booking website built on your domain

✓

Full tech stack deployed & configured (PriceLabs, HostBuddy, Breezeway, Hospitable)

✓

Listing copy consulting — written by us, published by you

✓

Automated guest communication workflows — built & handed to you

✓

Weekly pricing recommendations & market analysis

✓

Real-time owner dashboard & monthly performance report

Book a Strategy Call
Our Markets

Two of the Southeast’s
strongest STR corridors. One team.

We operate across Western North Carolina and the Smoky Mountains of Tennessee — two distinct, year-round markets with complementary seasons and consistent demand.

Aerial view of the Asheville, NC mountains
🏔 Western North Carolina

The Asheville Corridor

Year-round demand driven by arts & culture, outdoor recreation, and one of the South’s most celebrated food scenes. Fall color season creates surge demand unlike anywhere in the region.

$270+/night
Avg Nightly Rate
73%
Avg Occupancy
12mo
Year-Round
Communities we serve
AshevilleWeavervilleBlack MountainSwannanoaHendersonvilleBrevardWaynesvilleMaggie Valley
Great Smoky Mountains mist over the valley
🌪 The Smoky Mountains, TN

The Smokies Corridor

Home to America’s most-visited national park and one of the country’s highest-volume STR markets. Tens of millions of visitors annually create consistent, year-round demand.

$265+/night
Avg Nightly Rate
71%
Avg Occupancy
Top 5
US STR Market
Communities we serve
GatlinburgPigeon ForgeSeviervilleWears ValleyTownsendCosbyWalland
🏔 WNC Market Performance
Asheville
$285/night avg
74% occupancy
Black Mountain
$245/night avg
71% occupancy
Brevard
$230/night avg
69% occupancy
Waynesville
$220/night avg
68% occupancy
🌪 Smokies Market Performance
Gatlinburg
$275/night avg
72% occupancy
Pigeon Forge
$260/night avg
70% occupancy
Sevierville
$235/night avg
69% occupancy
Wears Valley
$250/night avg
71% occupancy

Want to know what your specific property could earn — including direct bookings?

Get My Free Revenue Estimate
What People Say

Trusted by property owners
across WNC & the Smokies.

★★★★★

“Hillside Stays completely transformed our rental. We went from stressing over every booking to just collecting deposits. Our revenue is up 30% and we haven’t had to deal with a single guest issue.”

JS
Jane S.Cabin Owner, Asheville
★★★★★

“The direct bookings website they built for us is a game changer. We’re saving thousands in OTA fees and our calendar has never been fuller. The SEO work alone paid for itself in the first month.”

MR
Mark R.Property Owner, Black Mountain
★★★★★

“I was skeptical about co-hosting, but Dylan and the team have been incredible. The systems they built — the website, the automated messaging, the pricing — it runs like a real business.”

KT
Karen T.Mountain Home Owner, Pigeon Forge
Dylan in the mountains of Western North Carolina
Meet the Founder

Hi, I’m Dylan —
Builder. Operator. WNC local.

Hi, I’m Dylan — a Western North Carolina local, builder, and STR systems nerd. I’ve called WNC home for over a decade, after graduating from Appalachian State University with a BSBA in Digital Marketing and Sales.

My career has been in early-stage and high-growth environments — sales, marketing, and operations — before finding my way into the short-term rental industry, where I worked in national sales operations helping clients buy and position STR properties across the country. That work gave me a front-row seat to what separates high-performing rentals from average ones. Almost every time, it came down to infrastructure.

Over time I realized: most STR property owners aren’t lacking opportunity. They’re lacking systems.

So I built Hillside Stays to solve that — not as another property manager, but as an advisory partner and systems builder for owners who want to operate well.

I bring the tech stack, the workflows, and the expertise. I share everything I know. And I work with a small number of owners at a time, by design — because doing this well requires genuine attention.

If you’re the kind of owner who wants to understand your operation, not just outsource it, let’s talk.

Let’s Talk About Your Property
Common Questions

Everything you need to know
before getting started.

It means we build your property a complete direct booking system — a custom website on your own domain, optimized to rank in local search, with a built-in booking engine and automated guest messaging. Guests can book directly with you, cutting out OTA platform fees entirely. Over time this channel compounds: more direct bookings, more revenue per night, and a guest list you actually own.

Your retainer covers ongoing advisory partnership — weekly pricing recommendations, system maintenance and optimization, performance reporting, and strategic support. The initial tech stack build (your direct booking website, HostBuddy configuration, PriceLabs setup, etc.) is completed during onboarding and included in your first month. Retainers start at $1,200/mo and are scoped based on your property and goals. We walk through the right fit on your strategy call.

No — we can start from scratch. Whether you have an existing listing or a property that’s never been listed, we handle the full setup during onboarding: listing copy consulting, tech stack configuration, pricing framework, and your direct booking site. You’ll own every account and every tool — we just build and configure it.

Your property stays yours. We build in owner-block periods whenever you need them. We ask for reasonable advance notice — especially during peak seasons — so we’re not canceling existing reservations, but you have full rights to use your own property.

We serve Western North Carolina including Asheville, Weaverville, Black Mountain, Old Fort, Swannanoa, Hendersonville, Brevard, Waynesville, Maggie Valley, and the surrounding mountain communities. We also serve the Smoky Mountain region of Eastern Tennessee, including Gatlinburg, Pigeon Forge, Sevierville, Wears Valley, Townsend, and surrounding areas. Not sure if your property qualifies? Reach out and we’ll let you know.

Our standard advisory agreement is a 6-month initial term, after which it renews month-to-month. We believe in earning your continued partnership — not locking you in. Either party can exit with 30 days written notice after the initial term.

We document property condition before and after every stay and file claims with Airbnb’s AirCover (up to $3M in host protection) or VRBO’s equivalent programs when damage occurs. We handle the entire claims process on your behalf, and we recommend maintaining a short-term rental rider on your homeowner’s insurance as an additional layer of protection.

Get Started

Let’s talk about
your operation.

Tell us about your property and where you’re at. We’ll follow up within 24 hours to schedule your strategy session — a focused conversation about your property, your goals, and whether Hillside Stays is the right fit.

📍Serving Western North Carolina & the Smoky Mountains
⌛Response within 24 hours
📧dylan@hillsidestays.net

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No spam. No pressure. Just an honest conversation about your property’s potential.

✓

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We’ll review your property details and get back to you within 24 hours with your free revenue estimate.

🔒

Existing Owner?

Access your property dashboard, view upcoming reservations, download earnings statements, and message our team.

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