Calaboose Retreat | Seasonal Outdoor Pool, Hot Tub, Pool Table, Firepit, Fireplaces

Looking for a private escape to relax, reconnect, and celebrate? This luxury 30-acre retreat is designed for unforgettable moments: perfect for family get-togethers, weddings, celebrations, corporate retreats, or intimate events in the heart of Red River Gorge. Look no further!
Plan your next getaway at Calaboose Retreat, our spacious 30-acre Red River Gorge estate made for big family getaways, group retreats, approved events, and memory-packed mountain stays. With a seasonal outdoor pool, private hot tub, stocked pond, separate pool house, pool table, bar area, fireplaces, firepit, massive wraparound porch, and room for up to 14 overnight guests, and space to host up to 50 event guests, Calaboose is built for gathering, relaxing, celebrating, and spreading out.

- Calaboose Retreat is a non-smoking, dog-friendly estate -

• Amenities include Wi-Fi, Smart TVs in every bedroom, seasonal fireplaces, washer and dryer, seasonal outdoor pool, massive & private hot tub, stocked catch-and-release pond with bluegill and catfish, pool table, bar area, wraparound porch, plenty of outdoor seating, firepit, propane grill with provided propane, and plenty of room to gather indoors and out. Pool floats, toys, and lifejackets are not provided.

• Kitchen + Dining: The main kitchen is built for big group meals, snack spreads, and slow mornings together. Amenities include a double wall oven, gas 6 burner stovetop, microwave, dishwasher, massive refrigerator and freezer, built-in ice maker, wine fridge, blender, toaster, standard drip coffee pot, plenty of cookware and dinnerware, 2 trash cabinets, and a huge island with additional seating for dining, serving, and meal prep. A Ninja CREAMi frozen treat maker is also provided for extra fun treats during your stay.

• Pool House: The pool house adds even more space to spread out, with a queen bedroom, full bathroom, pool table, bar area, and an additional refrigerator and freezer—perfect for extra drinks, snacks, and pool-day supplies.

• 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 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.

• Pond Note: The pond is stocked with bluegill and catfish and is catch-and-release only. Bring your own fishing gear and enjoy a peaceful day by the water.

• Approved Events: Approved events are allowed with prior approval only. Total occupancy for approved events is 50 guests, and overnight stays may not exceed 14 guests.

• 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/Sleeping Area: 2 Full Beds with Twin Pullouts + Ensuite Bathroom
- Pool House Bedroom: Queen Bed + Full Bathroom, not ensuite

• Bathrooms:
Calaboose Retreat has 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 bathroom.

• 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 please do not go upstairs into the carpeted areas. Dogs must be crated if left unattended inside the home.

• 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.

• 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 20-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 acres of pool days, pond views, hot tub nights, porch hangs, and firepit memories.

Still scrolling? Sounds like Calaboose Retreat already has your crew ready to break out of the ordinary. Go ahead and make that 30-acre Gorge getaway official.
- 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.
- Please be aware that no refunds are permitted for cancellations on holiday rates, which includes but is not limited to, New Year`s, Valentine`s Day, Memorial Day, 4th of July, Labor Day, Thanksgiving, and Christmas.