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Holiday Apartments in Monticello

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    All 37 Rentals in Monticello
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    Blue Cabin in Quiet Lake Community1 / 40
    (10)Excellent
    Monticello
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Monticello
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Scenic, Lakeview House, Located in Beautiful Woods1 / 4
    (1)Very good
    Monticello
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Monticello
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    The Tentrr - Hidden Hilltop Hideaway is on a homestead tucked in the wooded hills of beautiful southern Kentucky. This is an exclusive Tentrr site. Tentrr offers fully-equipped individual campsites on beautiful private land. Total seclusion in the woods, with the chance to experience the...
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    Location Information
    42633, Monticello, Kentucky
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    The following rentals are within 30 kilometres of Monticello.
    Conley Bottom Getaway1 / 20
    (1)Excellent
    Mill Springs
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Cable/satellite TV
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 March 2019
    I received a weekend stay here for a birthday present. My husband and two kids (ages 9 and 12), and myself live in Monticello, but we felt like we were far from home staying...
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    About this property
    NEW LISTING!!! This is the perfect place for a getaway at beautiful Lake Cumberland!! Our cozy house is located seconds away from Conley Bottom Marina. It is a newly remodeled 2 bdr, 1 ba home that sleeps 8. Inside you will find 2 bedrooms each with custom bunk beds. Both rooms have a queen bed on...
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    42633, Mill Springs, Kentucky
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 8
    Bronston
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    This beautiful condo is located overlooking the #7 Green. A really great kitchen, nicely decorated. Enjoy the night air as you set out on the screened porch. Located at Woodson Bend Resort, an all-inclusive resort on a 400 acre peninsula right on Lake Cumberland. While at the resort you can enjoy...
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    42518, Bronston, Kentucky
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Bronston
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    2 bedroom (Q, F) 2 bath condo on the golf course. Eat in kitchen, no dishwasher. Futon on the slider enclosed porch. Jacuzzi tub in the masterbath. Fireplace in the LR. Located at Woodson Bend Resort, an all-inclusive resort on a 400 acre peninsula right on Lake Cumberland. While at the resort...
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    42518, Bronston, Kentucky
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Bronston
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Two bedroom (Queen and 2 Twins), two bath condo . With a secluded and screened in porch for total relaxation. Open kitchen floor plan with washer/dryer. For those cool nights, a wood burning fire place for the ultimate relaxation. Booking of this unit is dependent on approval of owner. Located...
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    42518, Bronston, Kentucky
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Bronston
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    About this property
    You can be on vacation and still love cooking in this great kitchen. This is a beautifully decorated condo. It has a great lake view that you can enjoy from the screened in porch. Enjoy just sitting and taking in the view of Lake Cumberland. Life is good. 3 bedrooms with King, Queen & Bunk, Full &...
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    42518, Bronston, Kentucky
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Bronston
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Nicely decorated unit that offers two bath rooms and two bedrooms.(1 king bed and 2 twins) Sofa sleeper. Has a great view of the lake from the screened in porch. For the perfect family/friend get together the unit across the way, 92-1, is available for rent also. This combo would give you 5...
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    42518, Bronston, Kentucky
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Pleasant Valley1 / 19
    (2)Excellent
    Jamestown
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    Reviewed 3 April 2018
    Perfect place for a relaxing, get away from it all weekend..or longer. The house is very comfortable, cozy but not too small. Tastefully decorated, comfortable beds, fully...
    Reviewed 19 March 2018
    My husband and I are from ND and stayed here for a couple nights while we were in town visiting family. This house has everything you could need. The pool table and jukebox were...
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    About this property
    Located in the peaceful Harbor Springs community just 2.6 miles to the Jamestown Resort Marina. This 2000 square ft. Cabin features 3 bedrooms, 3 bath, full kitchen , entertainment room with full size pool table , jukebox, 60” LED TV with DVD and movies, wireless internet, cloths washer & Dryer....
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    42629, Jamestown, Kentucky
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Bronston
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    About this property
    Welcome to the Lake. Cute well equipped 3 bedroom 2 bath condo, new on the rental market. With a King, Queen, Double and 2 Twins there is room for the family. Relax on the screened in porch with your favorite book or beverage. New Large screen TV in the Living Room. Located at Woodson Bend...
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    42518, Bronston, Kentucky
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Bronston
    2 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    About this property
    Lower level lakeview 3 bedroom 2 bathroom condo. Great lake viewing from the screened in vinyl slider porch. Sleeps 9 with a King, 2 Twins, Bunkbed, Twin Sleeper sofa and a Single sleeper sofa. For the perfect family/friend get together the unit across the way, 92-1, is available for rent also....
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    42518, Bronston, Kentucky
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 9
    Bronston
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Beautifully decorated 3 bedroom/2bathroom condo with great view of the golf course. You will love this unit. Plenty of room for everyone. Has one king size bed, 1 queen size bed, two twins and a sleeper sofa. Enjoy the view from your very own screened in porch. Located at Woodson Bend Resort,...
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    42518, Bronston, Kentucky
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Bronston
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    This is a First floor 2 bedroom 1 bath golf view condo. Perfect for relaxing. Queen and 2 Twins, WiFi, Cable and grill. Also has a sleeper sofa. Just minutes from the pool, clubhouse and fitness room. Located at Woodson Bend Resort, an all-inclusive resort on a 400 acre peninsula right on Lake...
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    42518, Bronston, Kentucky
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    House on Lake Cumberland1 / 25
    (4)Excellent
    Burnside
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Washer
    • Balcony
    • Outdoor Dining Area
    • Mountain Views
    • Waterfront
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 October 2018
    We enjoyed the house very much.It was outfitted very well and we had no problems.If wanting to go back to that area, we would rent this house again!
    Reviewed 2 May 2017
    The house is Beautiful .It has everything that you would have in your own home so you can stay comfortably .The deck is a great place to hang out and cook on the grill .Denny...
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    About this property
    Nice 3 bedroom 2 bath house overlooking Lake Cumberland and Burnside Island. Just 1 mile from the entrance of Burnside Island, the largest, best ramp on Lake Cumberland. Ample parking on property for your boat and just minutes to gas station and ramp. Completely furnished. Stocked kitchen, all...
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    42519, Burnside, Kentucky
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Bronston
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Rustic and charm all in one. 3 bedroom (K,Q, 2 sets Bunkbeds) 3 bath (Jetted Tub in Masterbath) L shaped kitchen. The 3rd bedroom and bath is located in the Loft. One of the most awesome views on the resort. Any one would be pleased with this one. Located close to the golf course. Located at...
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    42518, Bronston, Kentucky
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Nancy
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Washer
    • Cable/satellite TV
    • Patio
    • Internet Access
    • Waterfront
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This house is a 3-story, wood-siding home with lake view. Private dock directly behind house. Boat ramp within 2 miles that puts you right on the main lake, just south of White Oak Creek. Home is approximately 3600 sf . Four (4) bedrooms (2 king/2 full), 3 bathrooms & 3 decks with access on each...
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    42544, Nancy, Kentucky
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    093-3 Condo1 / 24
    (1)Terrible
    Bronston
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    Gives you a home away from home feeling as you wrap yourself in nature and absorb the clean air. Totally renovated kitchen. 2 bedroom 2 bath with a Queen, 2 twins and a sleeper sofa in the living area. Wonderful screened in porch with vinyl sliders to create a 3 season room. Located at Woodson...
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    42518, Bronston, Kentucky
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Bronston
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    One of a kind, 3 bedroom 2 bath golf view condo. Sleeps up to 8 with a Queen, 2 Twins, Bunkbed and sleeper sofa. Screened in porch for relaxing with its own handpainted mural. Watch the golfers, enjoy the birds. Located at Woodson Bend Resort, an all-inclusive resort on a 400 acre peninsula...
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    42518, Bronston, Kentucky
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Hidden Cabin at Lake Cumberland Resort1 / 7
    (2)Very good
    Burnside
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Air Conditioning
    • Mountain Views
    • Hot Tub
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 August 2018
    Very nice cabin. Lots of time spent on deck. It does need more updated furniture though. You have to go up to bedroom to watch tv. No TV in living room.Overall, had a great time...
    Reviewed 21 July 2017
    Everything is minutes away from cabin.If your looking for a peaceful relaxing place to stay this is it..My family and I had a fantastic time and will return
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    About this property
    This is a private cabin located in Lake Cumberland Resort. This property has 3 Bedrooms and 2 and 1/2 Baths and is for rent for weekend and long term rentals. This unit comes completely furnished with a hot tub, fireplace, wrap around deck, furnished kitchen, TV, high speed internet, kitchen...
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    42519, Burnside, Kentucky
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
    The Oaks1 / 9
    (1)Excellent
    Nancy
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
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    • Hot Tub
    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 October 2018
    Very impressive quite and peaceful we really enjoyed it every thing was included kitchen towels sheets all we had to do was bring food and clothes
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    About this property
    The Oaks is located just minutes from Pulaski County Park and Lee’s Ford Marina. Situated on a quiet dead end street and wooded lot, The Homestead is the perfect place to relax after a long day on Lake Cumberland. Sit by the fire at the outdoor fire pit or relax in the hot tub. The Homestead is...
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    42544, Nancy, Kentucky
    Cabin Holiday Rental - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Nancy
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Chalet is located just minutes from Pulaski County Park and Lee’s Ford Marina. Situated on a quiet dead end street and wooded lot, The Homestead is the perfect place to relax after a long day on Lake Cumberland. Sit by the fire at the outdoor fire pit or relax in the hot tub. The Homestead is...
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    42544, Nancy, Kentucky
    Cabin Holiday Rental - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Bronston
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Pet friendly
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    About this property
    Cute 2 Bedroom 2 bath condo located on the #7 fairway. Perfect for your getaway. Screened porch for relaxing or watching the golf action. Located at Woodson Bend Resort, an all-inclusive resort on a 400 acre peninsula right on Lake Cumberland. While at the resort you can enjoy a great 18 hole golf...
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    42518, Bronston, Kentucky
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Hickory Ridge Guest House1 / 30
    (6)Excellent
    Albany
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Patio
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    • Outdoor Dining Area
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 August 2018
    Great place to stay. Just up the hill from Grider Hill Marina. House was really clean. Well stocked kitchen. Plenty of seating. The back left bedroom had a comfortable bed and...
    Reviewed 9 July 2018
    The Hickory Ridge House is amazing! So clean, well stocked with anything you may need for your visit. Great location close to Grider Hill marina. Thanks Preston, we will be...
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    About this property
    This is a home located within a quarter mile of Lake Cumberland and Grider Hill Resort. There are 3 bedrooms. One bedroom has a queen sized bed the other two bedrooms have full sized beds. The kitchen has a stove, refridgerator, a dish washer, coffee maker, toaster, and microwave. There is a...
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    42602, Albany, Kentucky
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Burnside
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Nice 2 bedroom(Q, 2T) 1 bath condo located witha view of the #7 fairway. Vinyl sliders on the porch for relaxing or watching the golfers. Located at Woodson Bend Resort, an all-inclusive resort on a 400 acre peninsula right on Lake Cumberland. While at the resort you can enjoy a great 18 hole...
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    42518, Burnside, Kentucky
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Nancy
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Cable/satellite TV
    • Wi-Fi
    • Private Garden
    • Air Conditioning
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Homestead is located just minutes from Pulaski County Park and Lee’s Ford Marina. Situated on a quiet dead end street and wooded lot, The Homestead is the perfect place to relax after a long day on Lake Cumberland. Sit by the fire at the outdoor fire pit or relax in the hot tub. The Homestead...
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    42544, Nancy, Kentucky
    Cabin Holiday Rental - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Ellie's Place- Beautiful Mountain Cabin Retreat1 / 12
    (2)Very good
    Burnside
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Grill
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    • Washer
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 April 2019
    The cabin was clean and cozy. Loved the screened in porch and hot tub. Especially enjoyed listening to the birds in the morning. It was easy to find, a quiet neighborhood with...
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    About this property
    Pack your bags for this great 3 bedroom, 3 bath Mountain Retreat Cabin. Located with the Gated Community of Lake Cumberland Resort. Home is fully furnished including linens and Kitchen ware. Relax on the screened back deck in a private hot tub. The home offers board games and a pool table for...
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    42519, Burnside, Kentucky
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Bronston
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    • Terrace
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A relaxing lakeside getaway awaits at this charming 2-bedroom, 2-bath Bronston vacation rental condo. Nestled along the shores of the scenic Lake Cumberland, you'll have serene forest views and easy access to endless outdoor recreation, including Cumberland Falls! Sitting on the 7th tee of the golf...
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    42518, Bronston, Kentucky
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Jamestown
    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Smoking allowed
    About this property
    Beautiful rustic yet charming farmhouse right on Lake Cumberland! We just underwent a HUGE renovation!! Don't miss out on this brand new listing as our bookings are coming fast! Located on 6.5 secluded acres of lakefront property in Jamestown, KY with seasonal lake view. Only 1.5 miles from...
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    42629, Jamestown, Kentucky
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
    Burnside
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Grill
    • Private Garden
    • Patio
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax on the back deck and enjoy the stunning view of Lake Cumberland in this conveniently located Vacation Home. The home offers 2 bedrooms, 2 baths with additional beds in family room. Back deck has gas grill and fire table and is located off kitchen. 3 Boat ramps including Burnside Marina are...
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    42503, Burnside, Kentucky
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Tateville
    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Kid friendly
    Smoking allowed
    About this property
    Sunbathe on the dock after swimming on Lake Cumberland and enjoy barbeques on the house-length deck with lake views. Accommodating 12 guests with 4 bedrooms and 2 bathrooms, this lakefront Bronston vacation rental home is located close to town where you can shop, dine and play. Shoot pool while...
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    42518, Tateville, Kentucky
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 12
    Albany
    6 Bedrooms, 3 Bathrooms, Sleeps 24 Quick View
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    • Wi-Fi
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fishing gear? Check. Boat? Check. Lakeside vacation rental with beds for the entire family? Check! Bring all your water gear, along with the whole crew, to this 6-bedroom, 3-bathroom cabin on Dale Hollow Lake! Easily access multiple marinas for water adventures or state parks for land excursions -...
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    42602, Albany, Kentucky
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 24
    Alpha
    5 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    • Grill
    • Patio
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    • Balcony
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The moment you step through the front door of this 5-bedroom, 3.5-bath Monticello vacation rental house, you'll be greeted by breathtaking views of Lake Cumberland. With an expansive deck, large outdoor patio, fire pit, and ideal Lake Cumberland location - ‘The Beaver Creek House’ is the ultimate...
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    42633, Alpha, Kentucky
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 16
    Mill Springs
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Balcony
    • Air Conditioning
    • Washer
    • Terrace
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Embark on a peaceful getaway to this charming 3-bedroom, 1.5-bath home. With 1,500 square feet of living space, this vacation rental provides an unforgettable escape with family or friends. Relax and soak up picturesque views from the spacious balcony, or enjoy a refreshing swim in Cumberland Lake....
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    Location Information
    42544, Mill Springs, Kentucky
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Albany
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay at this charming 2-bedroom 2-bath vacation rental to explore beautiful Lake Cumberland! Under 13 miles from several boat launches, this cabin offers a prime location for those trying to spend most of their time on the lake while retreating in a cozy cabin. There’s ample boat and trailer...
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    Location Information
    42602, Albany, Kentucky
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Burnside
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Garden
    • Secure Parking
    • Cable/satellite TV
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Awesome house short walk to boat ramp. House is in a gated community with three pools and a tennis court. The house is between Daniel Boone National Forest on one side and stunning Lake Cumberland on the other. One bedroom is located upstairs while the other two are located downstairs next to the...
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    Location Information
    42519, Burnside, Kentucky
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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