A winding fence on a grassy hill with horses grazing.

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

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, (216 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 CA $190
CA $543 total
includes taxes & fees
Sep 28 - Sep 29
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 CA $278
CA $567 total
includes taxes & fees
Sep 18 - Sep 19
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 CA $158
CA $381 total
includes taxes & fees
Oct 11 - Oct 12
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.

4. 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 CA $285
CA $618 total
includes taxes & fees
Sep 21 - Sep 22
4BR Lake Cumberland Cabin - Hot Tub, Fire Pit, Near Boat Ramps, Pet Friendly
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, (19 reviews)
"Wonderful place to stay for a few days on the lake with family. "
United States
Lena R.
The price is CA $346
CA $693 total
includes taxes & fees
Sep 24 - Sep 25
Harbor Hideway is a cozy, romantic gem minutes away from Jamestown Marina!
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
9.8 out of 10, Exceptional, (6 reviews)
"Really nice property, quite and full of nature."
United States
Terry R.
The price is CA $122
CA $414 total
includes taxes & fees
Sep 20 - Sep 21
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 CA $346
CA $696 total
includes taxes & fees
Oct 4 - Oct 5
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.
The price is CA $655
CA $1,131 total
includes taxes & fees
Sep 21 - Sep 22
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

Holiday Inn Express & Suites Somerset Central by IHG

Holiday Inn Express & Suites Somerset Central by IHG

10/10 Excellent
"😉"
Veronica 1-night trip
Posted 4 hours ago
Holiday Inn Express & Suites Somerset Central by IHG

Find out more about Monticello

Monticello Cottages information

Number of reviews
Accommodation
145 Cottages
Lowest Price
CA $381
Highest Price
CA $381

Frequently asked questions

How much do cottages in Monticello cost?
Cottages in Monticello range between CA $381 and CA $381 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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