A winding fence on a grassy hill with horses grazing.

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Monticello cottages

A wooden deck with a hot tub, a table, and chairs, surrounded by trees.

1. NEW TO VRBO May 2026 Secluded Adult themed Cottage in Kentucky

NEW TO VRBO May 2026 Secluded Adult themed Cottage in Kentucky
Science Hill
9.6 out of 10, Exceptional, (4 reviews)
"Really nice property, quite and full of nature."
United States
Terry R.
The price is £228
includes taxes & fees
23 Aug - 24 Aug
NEW TO VRBO May 2026 Secluded Adult themed Cottage in Kentucky
A covered porch with a blue exterior, a bright green door, and a seating area with a sofa and two side tables.

2. Lake Daze, Blue Cottage <1mile to Jamestown Marina with space to trailer boat.

Lake Daze, Blue Cottage <1mile to Jamestown Marina with space to trailer boat.
Jamestown
9.4 out of 10, Exceptional, (31 reviews)
"Great location, very comfortable, and pet friendly. We had friends at the campground behind the house, so it was great to walk over on the path in the back yard. We also checked out the state park and Lily Creek falls. Beautiful area!"
United States
Emily W.
The price is £289
includes taxes & fees
22 Aug - 23 Aug
Lake Daze, Blue Cottage <1mile to Jamestown Marina with space to trailer boat.
A stainless steel Cuisinart grill with four burners, a side burner, and a built-in oven, set against a wooden deck with a view of a leaf-covered park.

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

Peaceful Russell Springs Home w/ Fire Pit & Pond!
2.0 star property
Russell Springs
The price is £201
includes taxes & fees
22 Aug - 23 Aug
Peaceful Russell Springs Home w/ Fire Pit & Pond!
A cabin surrounded by dense forest, with a gravel path leading to it.

4. Harbor Hideway is a cozy, romantic gem minutes away from Jamestown Marina!

Harbor Hideway is a cozy, romantic gem minutes away from Jamestown Marina!
Jamestown
9.8 out of 10, Exceptional, (17 reviews)
"Wonderful place to stay for a few days on the lake with family. "
United States
Lena R.
The price is £374
includes taxes & fees
1 Sept - 2 Sept
Harbor Hideway is a cozy, romantic gem minutes away from Jamestown Marina!
A wooden deck with a table and chairs, surrounded by a wooden railing and a view of a forested area.

5. 4BR Lake Cumberland Cabin - Hot Tub, Fire Pit, Near Boat Ramps, Pet Friendly

4BR Lake Cumberland Cabin - Hot Tub, Fire Pit, Near Boat Ramps, Pet Friendly
Jamestown
9.6 out of 10, Exceptional, (10 reviews)
"This house was beautiful and perfect for what we needed. "
United States
Shavona M.
The price is £333
includes taxes & fees
26 Aug - 27 Aug
4BR Lake Cumberland Cabin - Hot Tub, Fire Pit, Near Boat Ramps, Pet Friendly
A single-story house with a covered porch, a small deck, and a front yard.

6. Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!

Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!
Jamestown
9.8 out of 10, Exceptional, (29 reviews)
"Excellent place to stay."
United States
Jason E.
The price is £408
includes taxes & fees
23 Aug - 24 Aug
Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!
A large, two-story house with a wrap-around porch, surrounded by lush green trees.

7. Restful Rustic Farmhouse on Lake Cumberland

Restful Rustic Farmhouse on Lake Cumberland
Jamestown
9.4 out of 10, Exceptional, (15 reviews)
"Our family had an amazing time at this vacation home! We had excellent communication with the owners and the place had everything we needed! Will definitely stay here again! Thank you for a wonderful holiday weekend!"
United States
Dana C.
The price is £535
includes taxes & fees
1 Sept - 2 Sept
Restful Rustic Farmhouse on Lake Cumberland
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Monticello Hotel Reviews

Cumberland Falls State Resort Park

Cumberland Falls State Resort Park

8/10 Good
"The stay we had was nice. The room was clean. Just a few updates would improve the room, hooks by bathroom sink area. paper towels in kitchen area and because we had a rainy morning and was inside for most of it. a bigger tv and more comfortable chairs because the bed wasnt comfotable to lay on to watch tv. But ovellrtay wad nice"
Donald 1-night trip
Posted 4 hours ago
Cumberland Falls State Resort Park

Find out more about Monticello

Monticello Cottages information

Number of reviews
106
Accommodation
142 Cottages
Lowest Price
£201
Highest Price
£535

Frequently asked questions

How much do cottages in Monticello cost?
Cottages in Monticello range between £201 and £535 per night. These retreats offer a chance to get in tune with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in Monticello with Expedia?
Reserving a cottage in Monticello is as easy as entering your travel dates and selecting your ideal place for a getaway in nature. From high-end retreats to budget-friendly properties and cottages that come with perks like a pool, Expedia has something for all styles. As for unbeatable deals? We've have them as well!
How can I find cheap cottages in Monticello?
Expedia can help you easily track down cheap cottages in Monticello. To lock in your dream stay in just a few keystrokes, try out the filter tool to tailor your search results by budget, star rating and amenities.
What is there to do in Monticello near my cottage?
The perfect travel accessory is a well-planned itinerary. Lake Cumberland Winery is a wonderful spot to start your exploration of Monticello.