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Distinct places. One curated collection.
Thoughtfully designed homes across five destinations, each rooted in nature and refined in every detail. Find your next gathering place.
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Curated
Homes worth the journey
Each property chosen for its setting, design, and soul.
Long Pond, PA
Hot Tub · Game Room · Fire Pit
Oak Haven
12
guests
5
bedrooms
3
baths
From $299 / night
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4.7 (240) Reviews
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Long Pond, PA
Hot Tub · Game Room · Fire Pit
Birchwood Estate
16+
guests
6
bedrooms
3.5
baths
From $299 / night
4.9 (250) Reviews
East Stroudsburg, PA
Sauna · Hot Tub · Fire Pit
Heronwood Retreat
12
guests
5
bedrooms
3.5
baths
From $349 / night
4.9 (545) Reviews
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Our story
Rooted in nature. Refined in design.
Five Oak Collection exists for travelers who crave more than a place to sleep. We believe the best gatherings happen in homes that inspire, where thoughtful design meets natural beauty and every detail serves a purpose.
Testimonials
Stories from Our Guests
Reflections on the spaces, details, and memories that made their stay unforgettable.
Stayed at the home for a spiritual retreat & couldn’t be happier with the home and host.
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Chanaly
6 years on Airbnb
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Comfy beds and linens! Our group loved the big tables for meals and games. Ryan was great at communicating throughout the trip.
Anna
New York
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This was a fantastic place to stay. The home was spotless, well-organized, and had everything we needed.
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Jonathan
Guest, Clearwater
Stayed at the home for a spiritual retreat & couldn’t be happier with the home and host.
Chanaly
6 years on Airbnb
Comfy beds and linens! Our group loved the big tables for meals and games. Ryan was great at communicating throughout the trip.
Anna
New York
This was a fantastic place to stay. The home was spotless, well-organized, and had everything we needed.
Jonathan
Guest, Clearwater
Destinations
Five places worth knowing
Each location chosen for its natural character and the gatherings it inspires. Discover where your next story begins.
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Poconos, PA
A serene escape into nature, with scenic views and peaceful surroundings. Perfect for unwinding and connecting with nature.
Explore Poconos.avif)
Clearwater, FL
Sunny beaches and vibrant nightlife await. A relaxing retreat by the water, ideal for sun lovers and explorers.
Explore Clearwater.avif)
Shenandoah Valley,
Discover the charm of rolling hills, vineyards, and quiet mountain retreats. A haven for outdoor enthusiasts.
Explore Shenandoah.avif)
Asheville, NC
An eclectic artsy city surrounded by stunning mountain landscapes. Explore local culture, art, and nature in perfect harmony.
Explore Asheville.avif)
Joshua Tree, CA
Experience the magic of desert landscapes and unique rock formations. A must-visit for stargazing, adventure, and tranquility.
Explore Joshua Tree
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Book Direct for Better Rates
Ready to Gather?
Your next chapter begins in a home made for it.
Contact
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