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Holiday rentals in Lake Cumberland

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Top-rated holiday rentals in Lake Cumberland

Guests agree: these stays are highly rated for location, cleanliness, and more.

Tiny home in Monticello
Adorable Tiny LakeView Cottage with kayaks!
Totally remodeled inside and out! We welcome your fur babies!! Adorable tiny house with a deck & bonfire pit overlooking a spectacular view of Otter Creek on Lake Cumberland. It is located in Monticello, Ky in a rural part of the area. It’s about 12 minutes to town. There is very close (driving distance) swimming access, kayaking, boating, boat ramps, fishing & marinas. Plus, your likely to see lots of wildlife. I have kayaks available for a small daily fee to rent. Pets allowed! $50/$75fee.
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Cabin in Winston
"Bison Hollow" Couples Cabin in the RRG
Paying homage to an American icon that once roamed Kentucky, "Bison Hollow" is the perfect couple's cabin to be your home base while enjoying the Red River Gorge. Newly constructed in 2021 and designed with a focus on comfort and unique details. It features reclaimed barn wood/bourbon barrel furniture, 1800’s hand hewn barn beams in the ceiling, large double shower, king size bed, and a wrap around porch with a hot tub perched in the canopies of the surrounding trees. Memories await you here!
Individual Host
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Cabin in Burnside
Cumberland Cabin Get Away
Come and get away! Relaxing cabin backing to the Daniel Boone National forest. Located in the Lake Cumberland Resort. This gated community offers swimming pools, tennis courts, easy boat ramp access, and security. Private setting provided in this cozy cabin is great for a couple and families. Private parking for 2 vehicles, fire pit, large covered back deck with LED lighting, and tons of movies and games for kids. Inside is decorated with antiques and has a great country farmhouse feel.
Individual Host
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Other great holiday rentals in Lake Cumberland

Cottage in Somerset
Cozy Lakefront Cottage Getaway with Relaxing View
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Cabin in Nancy
Serene 3 Bedroom Cabin with Hot Tub
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Cabin in Burnside
The Enchanted Hideaway /Pet Friendly with Hot Tub!
Professional Host
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Cabin in Burnside
Enchanted Chalet (17C)
Professional Host
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Cabin in Burnside
Romancing On The Cumberland
Professional Host
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Cabin in Nancy
Cozy Lake Cumberland Cabin - Hot Tub, Game Room
Cabin in Campbellsville
You & Me , Deer! Anniversary - Honeymoon Cabin
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Home in Somerset
Comfortable 2 bedroom cabin home
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Cottage in Somerset
Cozy Lakehouse with a View
Individual Host
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Treehouse in Cookeville
Cozy Cabin w/ Fast Wi-Fi, Fire Pit, 10 to Town
Individual Host
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Cabin in Bronston
Lake Cumberland retreat with views and hot tub!
Individual Host
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Cabin in McKee
Peaceful getaway, perfect for couples
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