Title: Lake Cumberland Winery in Monticello - Tours and Activities | Expedia.ca [Lake Cumberland Winery Hotels](https://expedia.ca/Lake-Cumberland-Winery-Hotels.0-l553248621560054943-0.Travel-Guide-Filter-Hotels)[Flights to Monticello](https://expedia.ca/Cheap-Flights-To-Monticello.d602030.Travel-Guide-Flights)[Lake Cumberland Winery Car Rentals](https://expedia.ca/Car-Rentals-In-Lake-Cumberland-Winery.d553248621560054943.Car-Rental-Guide)[Monticello Vacation Packages](https://expedia.ca/Monticello.d602030.Destination-Travel-Guides) # Lake Cumberland Winery Tours and Activities ## Visit Lake Cumberland Winery Activities [Monticello travel guide](https://expedia.ca/Monticello.dx602030) --- --- ## Plan a trip to see Lake Cumberland Winery Price found within the past 48 hours. Click for updated prices. ![Hancock House](https://images.trvl-media.com/lodging/43000000/42090000/42088700/42088671/27a6e10b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hancock House Downtown Louisville CA $1,227 per person Feb 28 - Mar 6 found 9 hours ago Roundtrip flight included Montreal (YUL) to Louisville (SDF) 8.2/10 Very Good! (245 reviews) The apartment was so elegant with an antique vibe. It had high ceilings and lots of tall windows with drapes and blackout blinds. Modern stainless steel kitchen appliances. I really liked that it had an icemaker and lamps in every room. Besides the stairs you couldn’t hear the neighbors.The host made things even more convenient by providing late or early check in, late check out or the option to add an extra night right from the confirmation email of your booking. If you like wholesome comfort and simple amenities you would love this charming apartment stay. Reviewed on Oct 31, 2025 ![Louisville Marriott Downtown](https://images.trvl-media.com/lodging/2000000/1120000/1111400/1111358/6dbe73d1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Louisville Marriott Downtown Downtown Louisville CA $1,238 per person Mar 26 - Mar 29 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Louisville (SDF) 9/10 Wonderful! (1,003 reviews) Room was spotless. Staff was top notch. Amenities as expected but I did expect a microwave in the room. There wasn't one. 9/10 experience. Will definitely book again! Reviewed on Jan 16, 2026 ![Hotel Distil, Autograph Collection](https://images.trvl-media.com/lodging/38000000/37770000/37765700/37765616/8fba23fc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Distil, Autograph Collection Downtown Louisville CA $1,322 per person Mar 26 - Mar 29 found 1 day ago Roundtrip non-stop flight included Toronto (YYZ) to Louisville (SDF) 9.6/10 Exceptional! (422 reviews) Exceptionally handsome hotel design, extraordinary restaurant and service, fantastic location. Reviewed on Jan 19, 2026 ### Popular places to visit ![Lots of history here. Historical mill and mansion. Beautiful waterfalls and scenery. ](https://images.trvl-media.com/place/602030/e986af9f-5b8e-4970-8ec0-95bf2907fa0c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Mill Springs Mill Park Explore the great outdoors at Mill Springs Mill Park, a lovely green space in Mill Springs. [](https://expedia.ca/Mill-Springs-Mill-Park-Monticello.d927864258782674944.Vacation-Attraction) ![1.7 mile trail and u can see the Cumberland falls and Eagle Falls I one trip...great few ](https://images.trvl-media.com/place/183256/15e1ab0c-bcd0-4e3d-aa2c-fc575d034280.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Lake Cumberland State Resort Park Explore the great outdoors at Lake Cumberland State Resort Park, a lovely green space in Jamestown. Stroll along the lakeside or seek out the fishing spots. [](https://expedia.ca/Lake-Cumberland-State-Resort-Park-Jamestown.d553248621532656065.Vacation-Attraction) #### Conley Bottom Marina Explore the waterfront in Monticello with a trip to Conley Bottom Marina. Wander the lakeside in this family-friendly area. [](https://expedia.ca/Conley-Bottom-Marina-Monticello.d927864680928677888.Vacation-Attraction) #### Cumberland Point Recreation Area Explore the great outdoors at Cumberland Point Recreation Area, a lovely green space in Nancy. Discover the area's museums and shops. [](https://expedia.ca/Cumberland-Point-Recreation-Area-Nancy.d927864614297862144.Vacation-Attraction) #### Fall Creek Recreation Area Explore the great outdoors at Fall Creek Recreation Area, a lovely green space in Monticello. Wander the lakeside in this relaxing area. [](https://expedia.ca/Fall-Creek-Recreation-Area-Monticello.d927864593192214528.Vacation-Attraction) #### Mill Springs Battlefield Explore the great outdoors at Mill Springs Battlefield, a lovely green space in Nancy. Amble around the area's parks or visit its shops. [](https://expedia.ca/Mill-Springs-Battlefield-Nancy.d927864260472770560.Vacation-Attraction) --- ## Best Lodging Options Near Lake Cumberland Winery ## Check availability on hotels close to Lake Cumberland Winery [Tonight ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621560054943&startDate=2026-01-21&endDate=2026-01-22)[Jan 21 - Jan 22](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621560054943&startDate=2026-01-21&endDate=2026-01-22) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621560054943&startDate=2026-01-22&endDate=2026-01-23)[Jan 22 - Jan 23](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621560054943&startDate=2026-01-22&endDate=2026-01-23) [This weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621560054943&startDate=23%2F01%2F2026&endDate=25%2F01%2F2026)[Jan 23 - Jan 25](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621560054943&startDate=23%2F01%2F2026&endDate=25%2F01%2F2026) [Next weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621560054943&startDate=30%2F01%2F2026&endDate=01%2F02%2F2026)[Jan 30 - Feb 1](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248621560054943&startDate=30%2F01%2F2026&endDate=01%2F02%2F2026) ![This charming cozy cottage has a private hot tub, deck for fishing.](https://images.trvl-media.com/lodging/30000000/29830000/29824000/29823912/68b5dc45_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### This charming cozy cottage has a private hot tub, deck for fishing. monticello KY [](https://expedia.ca/Monticello-Hotels-This-Charming-Cozy-Cottage-Has-A-Private-Hot-Tub.h29823912.Hotel-Information) ![Lake Cumberland vacation home, overlooking private fishing pond](https://images.trvl-media.com/lodging/31000000/30350000/30343100/30343037/75ba5791_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Lake Cumberland vacation home, overlooking private fishing pond Monticello KY [](https://expedia.ca/Monticello-Hotels-Lake-Cumberland-Vacation-Home.h30343037.Hotel-Information) ![Rustic Luxury Lakefront Cabin in Beautiful Wooded Surroundings](https://images.trvl-media.com/lodging/78000000/77810000/77808000/77807901/w1322h883x0y0-9809bcd4_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Rustic Luxury Lakefront Cabin in Beautiful Wooded Surroundings Nancy KY [](https://expedia.ca/Nancy-Hotels-Rustic-Luxury-Lakefront-Cabin-In-Beautiful-Wooded-Surroundings.h77807901.Hotel-Information) ![Stunning View of Lake Cumberland Within 1/8 Mile of Public Boat Ramp!](https://images.trvl-media.com/lodging/34000000/33970000/33961500/33961419/2c9cbe80_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Stunning View of Lake Cumberland Within 1/8 Mile of Public Boat Ramp! Nancy KY [](https://expedia.ca/Nancy-Hotels-Stunning-View-Of-Lake-Cumberland-Within-18-Mile-Of-Public-Boat-Ramp.h33961419.Hotel-Information) ![Brand new custom lake house with breathtaking panoramic views](https://images.trvl-media.com/lodging/105000000/104960000/104955000/104954922/0677dd13_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Brand new custom lake house with breathtaking panoramic views Nancy KY [](https://expedia.ca/Nancy-Hotels-Brand-New-Custom-Lake-House-With-Breathtaking-Panoramic-Views.h104954922.Hotel-Information) ![Best Access on Lake Cumberland! 4bedroom waterfront house on boat ramp in Nancy!](https://images.trvl-media.com/lodging/107000000/106340000/106332500/106332411/0490cbd0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Best Access on Lake Cumberland! 4bedroom waterfront house on boat ramp in Nancy! Nancy KY [](https://expedia.ca/Nancy-Hotels-Best-Access-On-Lake-Cumberland-4bedroom-Waterfront-House-On-Boat-Ramp-In-Nancy.h106332411.Hotel-Information) ![Lake house with boat ramp access across the street & tons of boat parking space.](https://images.trvl-media.com/lodging/60000000/59620000/59618700/59618692/ea2ee833_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Lake house with boat ramp access across the street & tons of boat parking space. Monticello KY [](https://expedia.ca/Monticello-Hotels-Lake-House-With-Boat-Ramp-Access-Across-The-Street-Tons-Of-Boat-Parking-Space.h59618692.Hotel-Information) ![6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more😍](https://images.trvl-media.com/lodging/89000000/88420000/88412500/88412425/e2d996e7_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### 6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more😍 Monticello KY [](https://expedia.ca/Monticello-Hotels-6Bedroom-Home.h88412425.Hotel-Information) ![Lake View Loft Cabin is only 2 miles from Wolf Creek Marina, Lake Cumberland KY](https://images.trvl-media.com/lodging/107000000/106890000/106881800/106881773/375a2975_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Lake View Loft Cabin is only 2 miles from Wolf Creek Marina, Lake Cumberland KY Nancy KY [](https://expedia.ca/Nancy-Hotels-Lake-View-LoftCabin-Is-Only-2-Miles-From-Wolf-Creek-Marina.h106881773.Hotel-Information) [See all 752 properties in Lake Cumberland Winery](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=553248621560054943) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. 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