At Oakcrest Hospitality, we merge executive-level precision, resort-quality standards, and design-forward hospitality to create exceptional short-term rental experiences. Every home we manage is a reflection of intentional design, strategic excellence, and genuine care.
We approach hospitality as both art and discipline — every decision, from layout to lighting, is guided by the principle that a well-run property should be as beautiful as it is functional.
From tranquil lake retreats to secluded mountain lodges, each Oakcrest property is a study in serenity and sophistication. Our interiors balance natural beauty with modern functionality — blending comfort, calm, and craftsmanship into every stay.
Every Oakcrest property embodies boutique-hotel-level design and operational excellence. From first impression to final detail, we ensure that both guests and owners experience seamless hospitality at the highest standard.
Through trusted partnerships with Krystal Klean and Kare, we deliver resort-level cleaning, maintenance, and care — ensuring every home remains guest-ready and pristine.
Our design philosophy celebrates nature’s quiet luxury. We curate spaces that complement their surroundings — whether overlooking a lake, hidden in the forest, or near mountain trails.
Each home invites guests to slow down, recharge, and reconnect — proving that hospitality can be both refined and restorative.
Behind every beautiful stay lies rigorous management. Oakcrest’s systems ensure consistency, safety, and efficiency across every home we operate.
From advanced STR compliance and maintenance tracking to intuitive guest communication, our structure allows owners to relax while guests experience hospitality that feels effortless.
Executive-level oversight ensuring protection, safety, and peace of mind.
Guiding investors with data, design insight, and long-term strategy.
Creating distinctive property identities through storytelling and design.
Data-informed pricing and performance tracking that drive profitability.
Transforming homes into boutique-quality retreats that stand out.
Delivered by our trusted partners — Krystal Klean and Kare — ensuring pristine presentation every time.
After two decades leading executive strategy, risk management, and performance initiatives, Jessica Southwell founded Oakcrest Hospitality to merge structure with soul.
Her leadership combines strategic expertise with a passion for design and people — redefining what it means to deliver boutique-level hospitality.
Every Oakcrest property embodies her belief that excellence is intentional — beautiful spaces, managed with integrity and care.
Yes! We welcome well-behaved pets so your whole family can enjoy the Poconos together.
We’re just minutes from Big Boulder and Jack Frost ski resorts, and within walking distance to several great local restaurants.
Yes, guests have easy lake access just a short walk from the chalet for kayaking, swimming, or relaxing by the water.
heck-in is after 4:00 PM, and check-out is by 11:00 AM. Early check-in may be available upon request.
Yes! Free on-site parking is available, along with a convenient EV charger for guests.
