Welcome to Calaboose Retreat, a luxury 30-acre Red River Gorge estate designed for unforgettable group stays, approved events, family gatherings, retreats, and elevated mountain getaways. This spacious private property offers the rare combination of comfort, privacy, and resort-style amenities—including a seasonal outdoor pool, private and massive hot tub, stocked pond, additional pool house, pool table, bar area, fireplaces, firepit, wraparound porch, and generous indoor and outdoor gathering spaces.
Calaboose Retreat sleeps up to 14 overnight guests and can accommodate approved events of up to 50 people, making it a standout setting for reunions, retreats, intimate weddings, celebrations, and special gatherings in the Red River Gorge area.
Spend your days swimming, fishing, grilling, hosting, exploring the Gorge, or relaxing across the main house and pool house. In the evenings, gather for hot tub soaks, firepit conversations, pool table tournaments, porch sitting, and peaceful country views.
Calaboose Retreat is more than a place to stay; it is a private, luxurious estate experience. Set on 30 acres, the property gives your group room to spread out, gather, celebrate, and enjoy the kind of amenities that turn a getaway into something truly memorable.
This property is ideal for:
- Family getaways
- Reunions
- Work Retreats
- Approved celebrations
- Intimate weddings
- Group stays with room to spread out
From pool days and catch-and-release fishing to group meals around the oversized kitchen island, evenings by the firepit, and quiet mornings on the wraparound porch, Calaboose Retreat was made for memory-making on a larger scale.
🏡 The Space
Main Kitchen + Dining
The main kitchen is designed for effortless group meals, celebratory dinners, snack spreads, and slow mornings together.
Kitchen features include:
• Double wall oven
• Gas stovetop
• Microwave
• Dishwasher
• Oversized refrigerator and freezer
• Built-in ice maker
• Wine fridge
• Blender
• Toaster
• Standard drip coffee pot
• Plenty of cookware and dinnerware
• 2 trash cabinets
• Oversized island with additional seating for dining, serving, and meal prep
• Ninja CREAMi frozen treat maker
Whether your group is preparing a full dinner, setting out pool-day snacks, serving brunch, or gathering around the island with coffee, the kitchen is built to support larger stays with ease.
🛋️ Living + Gathering Areas
Calaboose Retreat offers multiple comfortable spaces to gather throughout the property. Inside, guests can enjoy Wi-Fi, Smart TVs, fireplaces, a washer and dryer, spacious seating areas, and plenty of room to relax between meals, pool time, events, and Gorge adventures.
The wraparound porch and outdoor seating areas give your group even more space to enjoy the peaceful setting, whether you are starting the day slowly, winding down after a hike, or enjoying an evening together.
🏖️ Pool House
The pool house adds extra flexibility for group stays, event use, and pool-day convenience.
It is a perfect bonus space for drinks, snacks, games, relaxed hangouts, and keeping pool-day supplies close by.
The pool house includes:
• Queen Bedroom w/ Smart TV
• Full bathroom nearby, not ensuite
• Pool table
• Bar area
• Additional refrigerator and freezer
🛏️ Sleeping Arrangements
• Main House Master Bedroom: King Bed + Ensuite Bathroom
• Main House Bedroom 2: Queen Bed + Ensuite Bathroom
• Main House Bedroom 3: Queen Bed + Ensuite Bathroom
• Upstairs Bedroom: 2 Full Beds with Twin Pullouts + Ensuite Bathroom
• Pool House Bedroom: Queen Bed + Full Bathroom nearby
Maximum Overnight Occupancy: Comfortably sleeps up to 14 lucky overnight guests.
🚿 Bathrooms
Calaboose Retreat includes 5.5 bathrooms total. Each main house bedroom has an ensuite bathroom.
The master ensuite includes double vanities, a stand-up shower, and a walk-in closet.
The pool house bathroom is not ensuite.
All full bathrooms have stand-up showers only.
There is also one half guest bathroom in the main house.
🌿 Outdoor Living
The outdoor space is one of the standout features of Calaboose Retreat. Guests can enjoy a seasonal outdoor pool, private hot tub, stocked catch-and-release pond, wraparound porch, firepit, propane grill with provided propane, outdoor seating, and the privacy of a 30-acre estate setting.
The pond is stocked with bluegill and catfish and is catch-and-release only, so bring your fishing gear and enjoy a peaceful day by the water.
• Seasonal Pool Note: The outdoor pool is seasonal and is typically open from Memorial Day Weekend through Labor Day. Pool availability outside of these dates is not guaranteed. Reservations outside the stated pool season should be booked with the understanding that pool access will not be available. Pool floats, toys, and lifejackets are not provided.
• Pool Maintenance Note: We strive for every guest to enjoy a clean and well-maintained pool during their stay. Because of this, the pool is serviced regularly throughout the season, and our pool technician may occasionally need to stop by during a reservation for routine maintenance. We will always reach out to you and do our best to coordinate a time that works best for you, and visits are kept as quick and unobtrusive as possible.
🎉 Approved Events
Calaboose Retreat is available for approved events of up to 50 people, making it a beautiful setting for reunions, retreats, intimate weddings, celebrations, and special gatherings.
All events must be approved in advance. While approved events may include up to 50 people, overnight occupancy may not exceed 14 guests.
Additional visitors, vendors, event setup, parking needs, and event details must be discussed and approved prior to booking.
🐾 Pet Policy
Calaboose Retreat is dog-friendly with a $100 pet fee covering up to 2 dogs. Dogs only, please. Additional dogs may be considered with approval before booking and will incur a $50 fee per dog.
The owner requests that dogs do not go upstairs into the carpeted areas. Dogs must be crated if left unattended inside the home. Please reach out after booking to make sure the pet fee has been applied to your reservation.
🧺 Starter Essentials
Fresh linens and towels are provided. We also include an Essential Starter Pack to make your stay easier: 2 rolls of toilet paper per bathroom, 1 roll of paper towels, shampoo, conditioner, bar soap, 3 dishwasher pods, 3 laundry pods, 3 trash bags, and 1 fresh sponge.
🔥 Firewood + Grill
A propane grill is provided, and propane is included for your stay.
Firewood is not provided. We encourage purchasing firewood locally to help prevent the spread of invasive species and protect our beautiful wooded areas.
🚗 Parking + Access
Calaboose Retreat is accessible by 2WD vehicles under normal weather conditions. The route to the property is a blacktopped country road, and the property has a gravel driveway.
4WD is recommended during winter weather, snow, ice, or other inclement conditions.
For approved events, parking needs should be discussed prior to booking so we can make sure the property is a good fit for your group and event setup.
📍 Location
Calaboose Retreat gives your group a private estate-style place to unwind while still keeping Red River Gorge adventure within reach. The property is approximately 18 miles, or about a 23-minute drive, from Natural Bridge State Resort Park.
Spend your stay hiking, climbing, kayaking, canoeing, zip lining, sightseeing, visiting local restaurants, or taking scenic drives, then return to 30 private acres of pool days, pond views, hot tub nights, porch gatherings, and firepit memories.
Still scrolling? Sounds like Calaboose Retreat already has your attention. Don't let this one get away, book now!
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- Please contact us as soon as possible if you must cancel or reschedule your stay. No refunds or date modifications within 14 days or less of your arrival.
- No refunds are permitted due to weather. No exceptions. Winter weather (snow/ice) and flooding can occur in the area. You should be given the option to add Trip Insurance at booking check-out.
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