✨ If you're the one responsible for choosing the house, this is the kind of place everyone thanks you for later. 🌟
💰 The longer you stay, the more you save — discounts applied automatically at checkout.
❤️ Because here, in this spacious 5,500 sq ft home, true connection happens naturally.
🏡 Glencairn Knoll Estate
Where Teenagers Actually Hang Out with Grandparents
From age 5 to 85, everyone finds their thing here. And that's intentional.
This is a 5,500 sq ft private estate designed for multigenerational groups — large enough to spread out, intentional enough to bring everyone together. Two separate residential wings mean everyone has their own space. Four oversized king bedrooms with five king beds — and a queen pull-out sofa in the Speakeasy. Multiple hangout zones. Separate spaces for noise and quiet.
No one gets stuck with the bad room. No one feels crowded. No one asks, "So… what do we do now?"
Family reunions. Derby weekends. Bourbon Trail trips. Long-overdue gatherings.
"Our kids had a blast… we can't wait to visit again when we can stay longer." — Eric, Georgia "The entire family — from grandkids to grandparents — really enjoyed it." — Sarah
✨ What Makes Glencairn Knoll Different
🏡 Two Distinct Wings for Ultimate Privacy A true rarity. Grandparents can have the main-level master suite, while upstairs there are two wings to choose from — three bedrooms and the Speakeasy — providing real space and real privacy. It's the secret to a harmonious group vacation.
🏊 Heated Pool with Auto-Safety Cover The heart of the estate. Our 38-foot saltwater pool (with 8' deep end) is heated for an extended season. But the real luxury is the automatic safety cover — the peace of mind you need when traveling with little ones.
🍔 NEW — Blackstone 38", 4-Burner Grill + Poolside Dining The ultimate outdoor setup. Cook, relax, repeat.
🌟 Covered Hot Tub — usable year-round, rain or shine
🔥 Firepit with Adirondack Chairs — built-in evening gathering spot, firewood included, s'mores encouraged
🎤 Karaoke Lounge — the fastest way to get teens off their phones
🎱 Two Full Game Rooms — adults upstairs, kids downstairs, everyone happy
🛌 Five Luxurious King Beds No one gets the bad room. Four oversized bedrooms, five king beds, plus a queen pull-out. No awkward sleeping arrangements — just pure comfort.
🍽 Chef's Kitchen + Café-Style Coffee Bar — built for cooking for a crowd
🌲 3.75 Private Acres — room to roam, breathe, and play
🪦 A Private 1800s Cemetery on the Property A truly unique feature you won't find at any other home. Guests wander out to it. They talk about it long after the trip ends.
🎨 Rock Painting Station — rainy day creativity covered, plus a souvenir to take home
🐕 Proudly Pet-Friendly Because leaving a family member behind shouldn't be part of the stress. We welcome your dogs.
👶 Baby-Safe Throughout Safety gates, window guards, changing pad, Pack-n-Play, booster seat, and fireplace guards — all included.
🎁 Exclusive: The Secretariat Mystery Adventure Hidden throughout the home are framed pieces of Kentucky history — each one holding a clue. Follow them and you'll uncover the legend of Secretariat's missing ring. Find it, and your group wins a prize.
Kids crack the first clue. Grandparents know the history. Teenagers get competitive.
It happens every single stay.
"This place really does have it all." — Bria, Pennsylvania
🌅 A Day at Glencairn Knoll
You wake up. Coffee in hand.
Morning Rocking chairs on the front porch. Sunrise over rolling hills. Grandparents at the table with their second cup. Teens at the island. Little ones already planning pool time.
Afternoon With a simple push of a button, the automatic safety cover retracts — revealing the sparkling heated pool. Cannonballs in the deep end. Loungers under umbrellas. Cornhole tournaments on the lawn. Someone wanders off to explore a quiet piece of Kentucky history tucked among the trees. It's one of those details guests talk about long after the trip ends.
Evening Grilling for the gang on the 38", 4-burner Blackstone. Outdoor dining. Table for 10 plus a bar top for 2 — 12 seats total. One shared meal that lingers.
Then karaoke echoes from the basement. Bourbon gets poured in the Speakeasy. Marshmallows roast at the firepit. Conversations stretch longer than expected.
Night Pool lights glowing. String lights along the fence. Night swimming quickly becomes the highlight.
After Dark Flashlight tag across 3.75 acres.
Bedtime Everyone retreats to their own spacious room, comfortable king bed, and private corner of the house. The main-level master includes a deep soaking tub and walk-in rain shower guests describe as "like a spa."
Most groups plan to explore Kentucky. Most end up staying right here.
Take another look at the photos — you'll see how the spaces flow and how easily the house works for a group this size.
🛏 The Four Bedrooms — In Two Private Wings
Every bedroom is oversized and intentionally placed for privacy and comfort. Unlike other rentals with tiny rooms, here everyone gets a spacious retreat with a luxurious king bed.
No one is squeezed in. No one is compromising.
🌿 Main-Level Master Retreat King bed · Ensuite bath with soaking tub + rain shower · Ideal for single-level living
WEST WING
🥃 Bourbon Sunset Bedroom (Second Floor) Two king beds · Hall full bath
🍸 Upstairs Speakeasy Lounge (Second Floor) Bourbon-inspired separate lounge · Pull-out queen sofa · Shares hall bath with Bourbon Sunset Room
EAST WING
🌄 Derby Dawn Bedroom (Second Floor) King bed · Workspace · Covered deck access
🌾 Bluegrass Bedroom (Second Floor) King bed · Workspace · Shared covered deck
Derby Dawn & Bluegrass share one full bath and a washer/dryer area on the second floor. Bonus half bath near the main entry.
"Everyone slept so well… comfortable luxury." — Jean, Kentucky
👨🍳 The Kitchen — Famously Stocked
Built for real cooking — not reheating takeout. (Although Uber Eats does deliver here.)
6-burner gas range + double ovens
Two refrigerators — one in the kitchen, one in the mancave garage
Full coffee bar — Keurig, drip, French press, grinder, beans + grounds
Air fryer, Instant Pot, rice maker, waffle maker, blender, food processor, electric griddle, slow cooker
Spices, oils, condiments, cookware, bakeware — organized and labeled
You can cook a full holiday meal for 12 without improvising, with room for several chefs at once.
Dining for 12+ indoors and out. Meals and memories that last a lifetime.
🎱 Game & Play Zones
Mancave Garage Pool table · Poker table · Foosball · Darts · Oversized leather couch · Smart TV · Second fridge
"The game room in the garage was a great area for card nights." — Valerie, Pennsylvania
Basement Fun Zone An entire entertainment level.
🎤 Karaoke lounge · 🕹 Arcade games · 🏋️ Fitness room · 🎲 Board games · 🌾 Indoor AstroTurf play area
Rainy days don't derail the trip.
Rock Painting Station Supplies stocked and ready. A take-home memory for kids and adults alike.
🌳 The Outdoor Estate — 3.75 Acres
🏊 Heated 38-foot saltwater pool — auto cover, night lighting, 8' deep end ♨️ Covered hot tub — year-round, rain or shine 🔥 Firepit with Adirondack seating — firewood provided 🌲 Wide-open acreage for lawn games and late-night flashlight tag 🪦 Historic 1800s cemetery on the grounds — peaceful, historic, and something you genuinely won't find at another vacation rental in this area
"The grounds are worth the walk." — Jean, Kentucky
💻 Comfort & Practical Details
Gigabit WiFi (600+ Mbps)
Parking for 6+ cars
Upstairs washer/dryer
Pool towels provided
Pack-n-Play, booster seat, changing pad
Baby safety gates and window guards throughout
Fireplace guards for added safety
Smoke/CO detectors and fire extinguishers on every level
Spotless. Thoughtfully laid out. Fully equipped.
📍 Location — La Grange, Kentucky
25 minutes to downtown Louisville
Minutes to Bourbon Trail distilleries
Close to charming La Grange
Private acreage with easy highway access
✨ Why Families Return
"We will definitely be back." "It will be our annual spot." "Could not have been better." "We can't wait to visit again when we can stay longer."
Grandparents. Parents. Kids. Cousins. Everyone finds their place here.
💙 Built for Joy. Made for Generations.
Take one more look through the photos and picture your family here.
Take one more look through the photos and picture your family here — the porch, the pool, the firepit, everyone together.
If your dates are open, secure them. We can't wait to host you.
Permit: 24-050-STRP
