| .Clearview Acres | 2 | 4 | Analysis |
| 2 BR Cottage on the River | 2 | 4 | Analysis |
| A Little Piece of Versailles | 1 | 4 | Analysis |
| Ancient Oaks - Spacious Home - 6 mi to Keeneland | 2 | 4 | Analysis |
| Birdsong Valley on Bourbon Trail | 3 | 7 | Analysis |
| Bit and Bourbon | 2 | 4 | Analysis |
| Bluegrass Cottage | 2 | 4 | Analysis |
| Bluegrass Country Cottage | 1 | 4 | Analysis |
| Bourbon Barrel Cottages #2 on Ky. Bourbon Trail | 2 | 4 | Analysis |
| Bourbon Barrel Cottages #3 on Ky. Bourbon Trail | 2 | 4 | Analysis |
| Charming Apartment on the Bourbon Trail | 1 | 2 | Analysis |
| Charming Historic Home in Downtown Versailles | 2 | 4 | Analysis |
| Clean, Convenient, Cozy in Heart of the Bluegrass | 2 | 4 | Analysis |
| Cottage on Stephens /Downtown Midway | 3 | 6 | Analysis |
| Country Cottage -2 bedroom in Woodford County, Ky | 2 | 5 | Analysis |
| Country Cottage in Horse and Bourbon Country | 2 | 4 | Analysis |
| Cozy Cottage Downtown Versailles | 1 | 2 | Analysis |
| Creekside- Bourbon Trail Oasis | 2 | 4 | Analysis |
| Downtown Historic Home | 1 | 2 | Analysis |
| Downtown Midway Loft--Walk Everywhere! | 1 | 2 | Analysis |
| Dream farmhouse-in heart of horse&bourbon country | 4 | 10 | Analysis |
| EH Taylor Suite, The Woodford Hotel | 1 | 2 | Analysis |
| Farm Cozy Cottage- Views! Horses! Serenity! | 3 | 6 | Analysis |
| Four Roses Suite, The Woodford Hotel | 2 | 4 | Analysis |
| Garden view room on a farm | 1 | 2 | Analysis |
| Greenwood Farm log cabin-pet friendly | 3 | 6 | Analysis |
| Heritage Lodge - On A Farm! | 6 | 15 | Analysis |
| High style on the Bourbon Trail | 1 | 4 | Analysis |
| Hillside Farm & Creek - A Bourbon Trail Retreat | 1 | 4 | Analysis |
| Historic Woodford Buffalo Trace Distil - Sleeps 24 | 10 | 16 | Analysis |
| Kentucky breeze cabin | 3 | 8 | Analysis |
| Kentucky Horse Farm Barndo On The Bourbon Trail | 2 | 4 | Analysis |
| Limestone Landing - Cozy Luxury Retreat w/ HOT TUB | 3 | 6 | Analysis |
| Make your stay in Midway special | 1 | 2 | Analysis |
| Midnight Train to Midway | 2 | 4 | Analysis |
| Midway Cottage-Vineyard, Bourbon Trail, Horses | 3 | 6 | Analysis |
| Midway Home on 22 Acres Near Bourbon Trail! | 3 | 8 | Analysis |
| Midway Meadows Downtown on the Park | 2 | 4 | Analysis |
| Modern Remodeled Downtown Midway Studio | 1 | 2 | Analysis |
| Morgan Street Apartment | 2 | 4 | Analysis |
| Mystical, old world condo, w/ mid century charm. | 1 | 2 | Analysis |
| National Historic O'neal Cabin | 2 | 6 | Analysis |
| NEW Buffalo Trace Suite @ The Woodford Hotel | 1 | 2 | Analysis |
| NEW Woodford Reserve Suite @ The Woodford Hotel | 1 | 4 | Analysis |
| NEW! Blantons Bourbon Suite @ The Woodford Hotel | 1 | 4 | Analysis |
| Old Crow Suite, The Woodford Hotel | 1 | 2 | Analysis |
| Pappy VanWinkle Suite, The Woodford Hotel | 1 | 2 | Analysis |
| Perfect Access to All Things Bluegrass & Horses | 3 | 10 | Analysis |
| Private Pool 1901 Cottage, Keeneland Bourbon Trail | 1 | 3 | Analysis |
| Quiet, Comfy Cottage near Midway, KY | 2 | 6 | Analysis |