Rent The Cottages - Vacation Rentals in Lake Cumberland Winery

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From US $156

         

9.6 (119 Reviews)

House

Stunning View of Lake Cumberland Within 1/8 Mile of Public Boat Ramp!

• Air Conditioner
• Parking
• TV

• Kentucky
• Nancy

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From US $331

         

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10.0 (6 Reviews)

House

Fawn Run on Lake Cumberland

• Air Conditioner
• Parking
• Pet Friendly

• Kentucky
• Nancy

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From US $389

         

9.8 (64 Reviews)

House

Large 8 Bedroom Home Overlooking Play Area, And Pool. Great For Family Reunions.

• Air Conditioner
• Parking
• Pet Friendly

• Kentucky
• Monticello

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From US $775

         

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New

House

Lake and Boat Launch Access Modern Monticello Home

• Parking
• Security/Safety
• Sports/Activities

• Kentucky
• Monticello

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From US $149

         

9.8 (21 Reviews)

House

Comfortable lake living, pool access, 3 miles to marina

• Air Conditioner
• Parking
• Pet Friendly

• Kentucky
• Monticello

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From US $244

         

10.0 (130 Reviews)

House

Beautiful Vacation Home on Lake Cumberland, Monticello, KY

• Air Conditioner
• Parking
• TV

• Monticello
• Mill Springs

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From US $112

         

10.0 (57 Reviews)

House

Vacationers' Delight at Conley Bottom

• Air Conditioner
• Parking
• Pet Friendly

• Kentucky
• Monticello

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From US $193

         

10.0 (39 Reviews)

Cabin

Lake side Abode with a Spectacular year round View of the lake. 🌅

• Air Conditioner
• Parking
• TV

• Kentucky
• Nancy

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From US $193

         

10.0 (22 Reviews)

House

Cozy Ranch Home 1 Mile from CUMBERLAND POINT Boat Ramp. Owner Managed Property.

• Air Conditioner
• Parking
• TV

• Kentucky
• Nancy

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From US $560

         

10.0 (16 Reviews)

House

🌞The Abundant Life on Lakeshore🌞 - Lakeview Home <1/4 Mile to Public Boat Ramp

• Air Conditioner
• Parking
• TV

• Kentucky
• Nancy

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From US $428

         

10.0 (12 Reviews)

House

Cumberland Haven! One mile to Cumberland Point boat ramp and park.

• Air Conditioner
• Parking
• TV

• Kentucky
• Nancy

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From US $191

         

10.0 (10 Reviews)

Cottage

Newly remodeled, handicap accessible overlooking pool , play area

• Air Conditioner
• Parking
• Pool

• Kentucky
• Monticello

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From US $367

         

10.0 (9 Reviews)

House

Fawn Run on Lake Cumberland

• Air Conditioner
• Parking
• Pet Friendly

• Kentucky
• Nancy

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From US $243

         

10.0 (8 Reviews)

House

Big Foot's Retreat- is in walking distance of Cumberland Point Recreation Area

• Air Conditioner
• Parking
• Pet Friendly

• Kentucky
• Nancy

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From US $176

         

10.0 (6 Reviews)

Cottage

Cottage at Lake Cumberland; 6m walk to water at Clearwater public boat ramp

• Air Conditioner
• Parking
• TV

• Kentucky
• Nancy

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From US $661

         

10.0 (4 Reviews)

House

Spacious Lake Escape Near Conley Bottom

• Air Conditioner
• Parking
• TV

• Kentucky
• Monticello

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From US $303

         

10.0 (4 Reviews)

House

BRAND NEW 3 Bedroom Modern Barndominium at Lake Cumberland .5 mi to boat launch!

• Air Conditioner
• Parking
• TV

• Kentucky
• Nancy

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From US $222

         

10.0 (4 Reviews)

House

Retreat: Hot Tub & Huge Deck!

• Air Conditioner
• Parking
• Pet Friendly

• Kentucky
• Nancy

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From US $197

         

10.0 (4 Reviews)

House

Charming Getaway At Conley Bottom Resort/Lake Cumberland

• Air Conditioner
• Parking
• Pet Friendly

• Kentucky
• Monticello

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From US $77

         

10.0 (2 Reviews)

House

Dreamy Glamping Tent Near Conley Bottom

• Parking
• Balcony/Terrace
• Security/Safety

• Kentucky
• Monticello

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From US $308

         

10.0 (1 Review)

House

Cumberland Lake House W/Hot Tub

• Air Conditioner
• Parking
• TV

• Kentucky
• Monticello

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From US $99

         

10.0 (1 Review)

House

Stylish Skoolie Lake Cumberland

• Air Conditioner
• Parking
• Balcony/Terrace

• Kentucky
• Monticello

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From US $87

         

10.0 (1 Review)

RV Rental

Groovy Vintage RV In the Woods

• Air Conditioner
• Parking
• Balcony/Terrace

• Kentucky
• Monticello

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From US $77

         

10.0 (1 Review)

House

Enchanting Glamping Tent on Lake Cumberland

• Parking
• Balcony/Terrace
• Security/Safety

• Kentucky
• Monticello

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★ Pro Tip: Rentthecottages makes it easy to compare the best listings on Rentthecottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Rentthecottages homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Lake Cumberland Winery.