Stayifyoudare - Vacation Rentals in Lake Cumberland Winery

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From $162

         

9.6 (118 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 $331

         

|

10.0 (6 Reviews)

House

Fawn Run on Lake Cumberland

• Air Conditioner
• Parking
• Pet Friendly

• Kentucky
• Nancy

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From $240

         

10.0 (89 Reviews)

House

139 m² House ∙ 3 bedrooms ∙ 8 guests

• 1496 ft² House
• Air Conditioner
• Parking
• Pet Friendly

• Kentucky
• Nancy

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From $389

         

9.8 (63 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 $775

         

|

New

House

Lake and Boat Launch Access Modern Monticello Home

• Parking
• Security/Safety
• Sports/Activities

• Kentucky
• Monticello

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From $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 $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 $189

         

10.0 (85 Reviews)

Ski Chalet

Lake Cumberland vacation home, overlooking private fishing pond

• Air Conditioner
• Parking
• Pet Friendly

• Kentucky
• Monticello

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From $141

         

10.0 (53 Reviews)

House

Vacationers' Delight at Conley Bottom

• Air Conditioner
• Parking
• Pet Friendly

• Kentucky
• Monticello

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From $187

         

10.0 (38 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 $187

         

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 $518

         

10.0 (14 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 $428

         

10.0 (11 Reviews)

House

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

• Air Conditioner
• Parking
• TV

• Kentucky
• Nancy

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From $195

         

10.0 (10 Reviews)

Cottage

Newly remodeled, handicap accessible overlooking pool , play area

• Air Conditioner
• Parking
• Pool

• Kentucky
• Monticello

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From $373

         

10.0 (8 Reviews)

House

Fawn Run on Lake Cumberland

• Air Conditioner
• Parking
• Pet Friendly

• Kentucky
• Nancy

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From $227

         

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 $334

         

10.0 (5 Reviews)

House

BRAND NEW 3 BR, 2 BA Barndominium within 1/4 mile of neighborhood boat launch!

• Air Conditioner
• Parking
• TV

• Kentucky
• Nancy

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From $176

         

10.0 (5 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 $617

         

10.0 (4 Reviews)

House

Spacious Lake Escape Near Conley Bottom

• Air Conditioner
• Parking
• TV

• Kentucky
• Monticello

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From $286

         

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 $199

         

10.0 (3 Reviews)

House

Charming Getaway At Conley Bottom Resort/Lake Cumberland

• Air Conditioner
• Parking
• Pet Friendly

• Kentucky
• Monticello

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From $89

         

10.0 (2 Reviews)

House

Dreamy Glamping Tent Near Conley Bottom

• Parking
• Balcony/Terrace
• Security/Safety

• Kentucky
• Monticello

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From $308

         

10.0 (1 Review)

House

Cumberland Lake House W/Hot Tub

• Air Conditioner
• Parking
• TV

• Kentucky
• Monticello

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From $264

         

10.0 (1 Review)

House

Retreat: Hot Tub & Huge Deck!

• Air Conditioner
• Parking
• Pet Friendly

• Kentucky
• Nancy

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★ Pro Tip: Stayifyoudare makes it easy to compare the best listings on Stayifyoudare homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Stayifyoudare 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.