A winding fence on a grassy hill with horses grazing.

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Monticello cottages

A two-story building with a balcony, a covered outdoor seating area, and a small dock.

1. Unique Hexagon Cottage Atop Marina · Boat Parking · 3 En Suite Baths · Pets okay

Unique Hexagon Cottage Atop Marina · Boat Parking · 3 En Suite Baths · Pets okay
Jamestown
10.0 out of 10, Exceptional, (215 reviews)
"We felt like we were at home! Very clean and comfortable home with everything we needed. Communication with the host was flawless. This was my families first trip to Lake Cumberland and it was everything we thought it would be. Beautiful lake! We will definitely be coming back and staying at the Hexagon cottage again."
United States
Joleen
The price is €348
includes taxes & fees
23 Sept - 24 Sept
Unique Hexagon Cottage Atop Marina · Boat Parking · 3 En Suite Baths · Pets okay
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 €341
includes taxes & fees
8 Sept - 9 Sept
Lake Daze, Blue Cottage <1mile to Jamestown Marina with space to trailer boat.
A cabin surrounded by dense forest, with a gravel path leading to it.

3. 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, (18 reviews)
"Wonderful place to stay for a few days on the lake with family. "
United States
Lena R.
The price is €438
includes taxes & fees
8 Sept - 9 Sept
Harbor Hideway is a cozy, romantic gem minutes away from Jamestown Marina!
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.

4. 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 €236
includes taxes & fees
10 Sept - 11 Sept
Peaceful Russell Springs Home w/ Fire Pit & Pond!
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.
4BR Lake Cumberland Cabin - Hot Tub, Fire Pit, Near Boat Ramps, Pet Friendly
A wooden deck with a hot tub, a table, and chairs, surrounded by trees.

6. 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, (5 reviews)
"Really nice property, quite and full of nature."
United States
Terry R.
The price is €273
includes taxes & fees
8 Sept - 9 Sept
NEW TO VRBO May 2026 Secluded Adult themed Cottage in Kentucky
A single-story house with a covered porch, a small deck, and a front yard.

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

Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!
Jamestown
9.6 out of 10, Exceptional, (30 reviews)
"Great location. Host was nice and very attentive."
United States
Amber R.
The price is €435
includes taxes & fees
8 Oct - 9 Oct
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.

8. Restful Rustic Farmhouse on Lake Cumberland

Restful Rustic Farmhouse on Lake Cumberland
Jamestown
9.4 out of 10, Exceptional, (16 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.
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

Quality Inn & Suites Somerset Downtown

Quality Inn & Suites Somerset Downtown

10/10 Excellent
"My only complaint is that I didn't like the location of our room on the bottom floor ."
Bev 2-night trip
Posted 16 hours ago
Quality Inn & Suites Somerset Downtown

Find out more about Monticello

Monticello Cottages information

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Frequently asked questions

How much do cottages in Monticello cost?
Cottages in Monticello range between and 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.