Monticello Vacation Homes

A winding fence on a grassy hill with horses grazing.

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Our top choices for Monticello holiday homes

A cozy living room with a sofa, coffee table, and a painting on the wall.

1. The Cozy Cabell Cottage

Monticello

Whitley F.

HK$1,500 total

includes taxes & fees

27 Oct - 28 Oct

A hot tub with a woman relaxing, surrounded by plants and candles, set on a wooden deck with a forest view.

2. Lake Access ~ King Ensuites w/ fireplaces~ Hot Tub~ Fire Pit~ Boat Ramp

Monticello

Monika H.

HK$4,088 total

includes taxes & fees

27 Oct - 28 Oct

A modern kitchen with wooden cabinets, stainless steel appliances, and a central island with bar stools.

3. Lakeside Escape - Charming home centrally located on Lake Cumberland

Monticello

michelle d.

HK$1,946 total

includes taxes & fees

1 Nov - 2 Nov

A cozy room with a floral sofa, a TV, and a sign that reads "Everglow Hollow".

4. LAKE CUMBERLAND Get-a-Way! Charming House. BOAT RAMP NEARBY - Wifi - RV Hookups

Faubush

Morgan P.

HK$1,955 total

includes taxes & fees

27 Oct - 28 Oct

A building with a black front door, stone steps, and a wooden deck.

5. Cozy 1-bedroom house near lake Cumberland

Faubush

HK$1,648 total

includes taxes & fees

2 Nov - 3 Nov

A wooden interior with a wooden door, a wreath, a small table, and a vase of flowers.

6. Avery Acres

Albany

Josh W.

HK$1,859 total

includes taxes & fees

27 Oct - 28 Oct

A wooden porch with a white door, a cushion, a small table, and a wreath.

7. Wolf Creek Crossing Lake House Beach & Boat Launch .5 miles at Jabez Landing

Nancy

Brittany S.

A cozy living room with a sofa, a coffee table, and a TV. There is a kitchen with wooden cabinets and a bar area.

8. Country Comfort on Lake Cumberland!! 5 miles from Marina Rowena; Lake Cumberland

Albany

Eric G.

HK$2,525 total

includes taxes & fees

27 Oct - 28 Oct

A rural landscape with a small house, a pond, and trees.

9. Lake Cumberland Pond View

Russell Springs

Kevin K.

HK$3,244 total

includes taxes & fees

4 Nov - 5 Nov

A wooden deck with a ceiling fan, a brick wall, and a view of a forest.

10. Charming 1-bedroom fish shack in Somerset with WiFi and AC

Somerset

Chris R.

HK$1,146 total

includes taxes & fees

28 Oct - 29 Oct

A living room with a fireplace, a sofa, and a television mounted on the wall.

11. Eagles Nest Lake Retreat

Russell Springs

Melanie T.

HK$1,621 total

includes taxes & fees

9 Nov - 10 Nov

A spacious living area with a high ceiling, a dining table, and a kitchen in the background.

12. Frank's Bird House | Lake Views + Game Room

Pulaski County

"I can't say enough great things about Frank's Bird house!! It was perfect for my husband and I and a family gathering. Plenty of room, the place was immaculate clean and just stunning. Our nieces and nephew loved the downstairs area with the pool table and theater system for some movies with the family! Saw lightning bugs and deer. We have a disabled family member and the top floor worked perfect with a covered porch on the front and beautiful views from 2 back balconies with sliding glass...

brandy m.

HK$3,919 total

includes taxes & fees

27 Oct - 28 Oct

A modern kitchen with white cabinets, granite countertops, stainless steel appliances, and a large island with bar stools.

13. Remodeled House Near Jamestown Marina, Room to Park Your Boat in Driveway!

Jamestown

Jennifer L.

HK$3,259 total

includes taxes & fees

14 Nov - 15 Nov

A modern kitchen with white cabinets, a wooden countertop, and a dining area with a table and chairs.

14. Cozy Lake Time Retreat

Jamestown

Matthew G.

HK$2,097 total

includes taxes & fees

27 Oct - 28 Oct

A spacious living area with a kitchen, a dining table, a sofa, and a rocking chair.

15. Spacious 3-Bed Townhome in Charming Somerset with the Ideal Location.

Somerset

Kara B.

HK$1,565 total

includes taxes & fees

29 Oct - 30 Oct

Exterior | Fire Pit w/ Seating | Covered Patio & Porch

16. Peaceful Russell Springs Home w/ Fire Pit & Pond!

Russell Springs

Delmar B.

HK$2,187 total

includes taxes & fees

27 Oct - 28 Oct

A modern kitchen with white cabinets and stainless steel appliances, a dining area with a round table and chairs, and a living room with a sofa and a coffee table.

17. Welcome to the your budget friendly stop right off the highway 27.

Somerset

Teresa G.

HK$921 total

includes taxes & fees

2 Nov - 3 Nov

A wooden deck with a railing, a ceiling fan, and a view of trees in the background.

18. Calming 1-bedroom yellow door house close to lake with Wi-Fi, AC

Somerset

Pascal C.

HK$1,396 total

includes taxes & fees

29 Oct - 30 Oct

A kitchen with wooden walls, stainless steel appliances, and a chalkboard sign.

19. The Lodge Lake Retreat – Family-Friendly with Private River Access

Jamestown

Dillon R.

HK$2,092 total

includes taxes & fees

9 Nov - 10 Nov

A modern kitchen with a central island, bar stools, a fireplace, and a ceiling fan.

20. Relaxing Country Getaway, 3BR/2Bath

Stearns

Kimberly K.

HK$2,024 total

includes taxes & fees

29 Oct - 30 Oct

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Top Monticello Hotel Reviews

Cumberland Falls State Resort Park

10/10 Excellent

"This cabin/resort was everything we needed for a relaxing evening in nature. We hiked down to the waterfall and brought food that could be heated in the microwave. It was beautiful in the fall with the leaves on the ground."

4 Bedrooms, Heated Private pool, hot tub, Game room, and Water Front View!

10/10 Excellent

"Our group spent a beautiful fall weekend in this beautiful home in a gorgeous setting overlooking the lake. The kitchen was the best stocked kitchen of any we’ve ever rented! Plenty of cookware for all our meals together. The hot tub was a nice relaxing addition for an afternoon soak. All the bedrooms were spacious and comfortable for each couple and the living spaces were uber comfy and just right. And the home was close enough for day trips for kayaking on the lane and hiking at Cumberland State Park. Highly recommend All of this!. We’ll be back!"

Lake Bluff Paradise on Lake Cumberland. Game Room and Hot Tub Sept 15-May 15!

10/10 Excellent

"The house is beautiful, very spacious, and quiet with great views. We had a couple minor issues that we needed to reach out to the owners on and they were very quick to respond and attentive to our needs. Our family loved the home and was the perfect setup for us. We agree that we would return her again for future stays in the area."

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