A winding fence on a grassy hill with horses grazing.

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Monticello cottages

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.

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

Peaceful Russell Springs Home w/ Fire Pit & Pond!
2.0 star property
Russell Springs
$249 nightly
The price is $274
Oct 20 - Oct 21
Total with taxes and fees
Peaceful Russell Springs Home w/ Fire Pit & Pond!
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.
$372 nightly
The price is $410
Oct 20 - Oct 21
Total with taxes and fees
Lake Daze, Blue Cottage <1mile to Jamestown Marina with space to trailer boat.
A wooden deck with a table and chairs, surrounded by a wooden railing and a view of a forested area.

3. 4BR Charming Cabin Retreat | Hot Tub, Fire Pit

4BR Charming Cabin Retreat | Hot Tub, Fire Pit
Jamestown
9.6 out of 10, Exceptional, (10 reviews)
"This house was beautiful and perfect for what we needed. "
United States
Shavona M.
$387 nightly
The price is $396
Oct 21 - Oct 22
Total with taxes and fees
4BR Charming Cabin Retreat | Hot Tub, Fire Pit
A single-story house with a covered porch, a small deck, and a front yard.

4. 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, (31 reviews)
"Great place!"
United States
ashley k.
$456 nightly
The price is $503
Oct 20 - Oct 21
Total with taxes and fees
Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!
A cabin surrounded by dense forest, with a gravel path leading to it.

5. 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
9.6 out of 10, Exceptional, (20 reviews)
"Wonderful place to stay for a few days on the lake with family. "
United States
Lena R.
$456 nightly
The price is $503
Oct 20 - Oct 21
Total with taxes and fees
Harbor Hideway is a cozy, romantic gem minutes away from Jamestown Marina!
A large, two-story house with a wrap-around porch, surrounded by lush green trees.

6. Restful Rustic Farmhouse on Lake Cumberland

Restful Rustic Farmhouse on Lake Cumberland
Jamestown
9.6 out of 10, Exceptional, (17 reviews)
"Wonderful home and great stay with great amenities and close to the lake."
United States
Grant A.
$714 nightly
The price is $787
Oct 20 - Oct 21
Total with taxes and fees
Restful Rustic Farmhouse on Lake Cumberland
A wooden deck with a hot tub, a table, and chairs, surrounded by trees.

7. 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, (9 reviews)
"Really nice property, quite and full of nature."
United States
Terry R.
$326 nightly
The price is $359
Oct 20 - Oct 21
Total with taxes and fees
NEW TO VRBO May 2026 Secluded Adult themed Cottage in Kentucky
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

Comfort Inn Somerset - Lake Cumberland

Comfort Inn Somerset - Lake Cumberland

10/10 Excellent
"The stay was truly delightful, offering a perfect blend of comfort and elegance that exceeded every expectation. Every member of the staff greeted us with a genuine smile and ensured that our needs were addressed with the utmost care. The room was exceptionally clean, beautifully designed, and provided a peaceful sanctuary for much-needed relaxation. Dining here was a good culinary featuring a variety of . It is a pre to recommend this establishment to"
Eugene 1-night trip
Posted 4 hours ago
Comfort Inn Somerset - Lake Cumberland

Find out more about Monticello

Monticello Cottages information

Number of reviews
109
Accommodation
144 Cottages
Lowest Price
$274
Highest Price
$787

Frequently asked questions

How much do cottages in Monticello cost?
Cottages in Monticello range between $274 and $787 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.

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