| "Beary" Cute Hot Tub Cabin @ LakePointe Resort | 2 | 6 | Analysis |
| "The Bullpen" Lakeside Cabin with the soul of a Beach Cottage. | 2 | 8 | Analysis |
| 'Hickeys Hideaway' - Walk to Lake, Near Somerset | 3 | 8 | Analysis |
| 2-Bedroom Cabin@LakePointe Resort-no cleaning fee! | 2 | 6 | Analysis |
| 2-Bedroom Cabin@LakePointe Resort-no cleaning fee! | 2 | 6 | Analysis |
| 4 bed 2 bath by Jamestown Marina | 4 | 10 | Analysis |
| A True Guest Favorite! Photos soon! Updating B&B! | 2 | 4 | Analysis |
| Abundant Life On Lakeshore - Boat Ramp < 1/4 Mi | 5 | 12 | Analysis |
| Apple Valley Lake Cumberland Pool open till Oct 13 | 2 | 6 | Analysis |
| Barndo Bliss: Luxury King Suites, Spa, Fire Pit | 4 | 12 | Analysis |
| Beautiful lake view cabin on Lake Cumberland | 4 | 8 | Analysis |
| Beautiful New Cabin 4 mins from Cumberland Lake | 1 | 6 | Analysis |
| Blue Cat Cabin | Lake Cumberland Cozy Retreat | 2 | 4 | Analysis |
| Bluegrass Gables: Lake Cumberland Cottage | 4 | 12 | Analysis |
| Bunk House at Foggy Bottom | 1 | 8 | Analysis |
| Cabin in the Woods | 3 | 15 | Analysis |
| Cabin in the Woods @ LakePointe - no cleaning fee! | 2 | 6 | Analysis |
| Cabin in the woods-near Cumberland River | 3 | 6 | Analysis |
| Catch and Relax on Main! | 3 | 7 | Analysis |
| Clifty Creek Inn—Unit A | 1 | 5 | Analysis |
| Clifty Creek Inn—Unit B | 1 | 5 | Analysis |
| Close to Jamestown dock | 5 | 10 | Analysis |
| Country Haven | 2 | 5 | Analysis |
| Cozy Lake Cumberland Cabin - Hot Tub, Game Room | 2 | 8 | Analysis |
| Cozy Lake Getaway | 1 | 7 | Analysis |
| Cozy Lake Time Retreat | 3 | 6 | Analysis |
| Crow's Nest (A.K.A. Roughing It) at Foggy Bottom | 4 | Analysis | |
| Cumberland Cabin | 3 | 7 | Analysis |
| Cumberland Get-A-Way llc | 2 | 9 | Analysis |
| Cumberland Lake Retreat | 3 | 8 | Analysis |
| Cumberland-Get-A-Way LLC | 5 | 16 | Analysis |
| Da Bears Den Lakeside Retreat | 3 | 9 | Analysis |
| Delightful 1 bedroom RV with 2nd bed option | 1 | 4 | Analysis |
| Dream cabin with mancave&views of Lake Cumberland. | 3 | 8 | Analysis |
| DRIFT INN only 10 minutes to Jamestown Marina | 4 | 12 | Analysis |
| Driftwood Cottage with HotTub on Lake Cumberland | 4 | 8 | Analysis |
| Eagle's Nest | 2 | 4 | Analysis |
| Eagle's Nest Lake Retreat | 2 | 6 | Analysis |
| Gran's Place | 3 | 6 | Analysis |
| Harbor Hilltop at Cumberland | 3 | 6 | Analysis |
| Harbor Springs, Jamestown Cabin | 4 | 8 | Analysis |
| HillTop Hideaway #9 | 2 | 6 | Analysis |
| Home 0.2 miles from boat ramp with game room | 2 | 8 | Analysis |
| Home by Wolf Creek Marina & Boat Ramp Pets Welcome | 1 | 4 | Analysis |
| Hoosier Hideaway-Cozy 2-Bedroom Cabin Near LCM | 2 | 6 | Analysis |
| Hot Tub~Firepit~Riverfront~Near Lake Cumberland | 2 | 6 | Analysis |
| Idol Time Cabin at Lake Cumberland - Clearwater | 1 | 6 | Analysis |
| Ina's Place | 3 | 8 | Analysis |
| Jabez Lake Retreat #1 | 1 | 4 | Analysis |
| Jamestown - KY Lake Cottage | Boat Parking | 3 | 6 | Analysis |