A guest laughing beneath a canopy of string lights at a Pretty Creative event

Hospitality & Destinations

Build a destination people travel for.

Pretty Creative helps boutique hotels, retreat properties, cabins, restaurants, wedding venues, and experience-led places become more distinctive, more bookable, and more valuable.

Who we serve

Places with a point of view, and the owners behind them.

Boutique hotels · Inns · Cabins · Retreat properties · Wedding venues · Restaurants · Campgrounds · Experience-led stays · Tourism and lifestyle businesses

The business opportunity

Not just more visibility. More value.

If Booking.com and Airbnb are filling most of your calendar, they’re also keeping the guest relationship and the margin that should be yours. A distinctive property earns more than bookings. Stronger positioning supports stronger rates. Direct bookings protect margin from commission platforms. Retreats, weddings, and group offers turn quiet seasons into revenue. And a guest journey worth returning to compounds — reviews, referrals, and repeat stays that no ad budget can buy.

Good design gets attention. A complete experience earns loyalty.

Jenn Dieas seated before the Bahá'í House of Worship in Wilmette

The Destination Framework

From first impression to return visit, we design the full journey.

01

Position

Clarify the property’s strongest story, ideal guest, competitive difference, and most valuable revenue opportunities.

02

Present

Build the brand, messaging, website, photography direction, and digital experience.

03

Attract

Create content, campaigns, creator partnerships, local collaborations, and direct demand.

04

Convert

Improve inquiries, booking paths, packages, email capture, and sales follow-up.

05

Return

Strengthen the guest experience, reviews, referrals, repeat stays, and post-visit communication.

Engagements

Ways we work with properties

01

Destination Strategy

For owners who need clarity before making a larger investment.

  • Brand and property audit
  • Guest and market positioning
  • Direct-revenue opportunities
  • Retreat, wedding, event, and group potential
  • Guest-journey review
  • Prioritized 90-day action plan

02

Destination Build

For properties ready for a meaningful transformation.

  • Positioning
  • Messaging
  • Brand identity or refinement
  • Website
  • Direct-booking journey
  • Content direction
  • Offer development
  • Launch or relaunch strategy

03

Destination Growth

For properties that need an ongoing strategic and creative partner.

  • Campaign strategy
  • Content direction
  • Creator partnerships
  • Email marketing
  • Direct-booking growth
  • Seasonal packages
  • Retreat and event promotion
  • Conversion improvements
  • Strategic guidance
A considered guest lounge with velvet chairs

Direct-booking strategy

Create more reasons to book directly.

Commission platforms are a discovery channel, not a business model. We build the story, website, booking path, packages, and email systems that give guests a better reason to book with the property itself — and give the property a direct relationship it owns.

Retreats · Weddings · Groups

The revenue hiding in your quiet seasons.

Retreats, weddings, and group stays are the highest-value bookings most properties never structure. We help owners shape the offer — concept, guest journey, programming, partners, and pricing — so the property fills the calendar it already has.

We have designed and hosted retreats ourselves, so the plan accounts for what the brochure never shows: logistics, staffing, margins, and the moments guests actually remember.

Creator partnerships

Creators who genuinely fit.

We connect distinctive properties with creators whose audience, taste, and reason to visit align with the brand — then build collaborations around useful content, hosted stays, and measurable business goals. Not generic influencer marketing.

Creator sourcing · Hosted stays · Campaign concepts · Content usage planning · Launch partnerships · Wedding and retreat visibility · Local ambassador programs · Ongoing creator relationships

What this looks like

We’ve been on both sides of the feature.

Before Pretty Creative, co-founder Jenn was the story: one of YouTube’s largest tiny-living channels — 1.88M subscribers — featured her converted-van home to nearly 100,000 viewers. That’s the same alignment we source for clients: the right creator, the right audience, a reason to visit that actually holds up.

Watch on YouTube

Experiences we design

Ways to gather people.

We do not plan these on paper and hand them off. We concept, program, staff, and host them ourselves — which is why they work in the room.

Jenn Dieas seated in a calm namaste pose beside a bird-of-paradise plant

Retreats

Multi-day gatherings we concept, program, staff, and host — the guest journey, the partners, the meals, the pacing, and the rooms people talk about afterwards.

A brand photoshoot in progress — photographer framing a founder against a white studio wall

Brand Building

Working sessions for founders that double as production days — we host brand photoshoots inside the experience, so you leave with the positioning and the library of images to launch it.

Guests around tables at a hosted workshop, neon script glowing behind them

Community Events

Workshops, coffee chats, and meetups run on a rhythm — the small, recurring rooms that turn a place into somewhere people belong rather than somewhere they visited once.

Three women in matching branded dresses walking a Chicago sidewalk together

Brand Activations

Launch moments, press previews, and pop-ups — Press & Glow among them — staged so the night produces coverage, content, and relationships that keep working long after it ends.

Start a hospitality project

Places worth traveling for. Businesses worth returning to.

Tell us about the property — where it is, what it does well, and what you want it to become. We will come back with an honest read on the opportunity.

Tell us about your property