A winding fence on a grassy hill with horses grazing.

Search Monticello Cottages

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Monticello cottages

An outdoor patio with a grill, two chairs, and a table.

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
Nov 14 - Nov 15
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.
$337 nightly
The price is $372
Nov 14 - Nov 15
Total with taxes and fees
Lake Daze, Blue Cottage <1mile to Jamestown Marina with space to trailer boat.
A wooden deck with a railing overlooking a forested area.

3. 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, (224 reviews)
"Appreciate how easy it is to commute with the owner and the house is always very clean. This is our 4th stay here!"
United States
Jennifer S.
$358 nightly
The price is $394
Nov 15 - Nov 16
Total with taxes and fees
Unique Hexagon Cottage Atop Marina · Boat Parking · 3 En Suite Baths · Pets okay
A wooden deck with a table and chairs, surrounded by a wooden railing and a view of a forested area.

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

4BR Charming Cabin Retreat | Hot Tub, Fire Pit
Jamestown
9.8 out of 10, Exceptional, (11 reviews)
"This house was beautiful and perfect for what we needed. "
United States
Shavona M.
$400 nightly
The price is $409
Nov 17 - Nov 18
Total with taxes and fees
4BR Charming Cabin Retreat | Hot Tub, Fire Pit
A house with string lights and a fire pit in the yard.

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.
$433 nightly
The price is $477
Nov 15 - Nov 16
Total with taxes and fees
Harbor Hideway is a cozy, romantic gem minutes away from Jamestown Marina!
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, (32 reviews)
"Great place!"
United States
ashley k.
$433 nightly
The price is $477
Nov 15 - Nov 16
Total with taxes and fees
Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!
An aerial view of a house surrounded by dense forest with a river in the background.

7. 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.
$684 nightly
The price is $754
Dec 9 - Dec 10
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.

8. 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, (10 reviews)
"Really nice property, quite and full of nature."
United States
Terry R.
$310 nightly
The price is $342
Nov 15 - Nov 16
Total with taxes and fees
NEW TO VRBO May 2026 Secluded Adult themed Cottage in Kentucky
A residential building with a symmetrical facade, a stone foundation, and a well-maintained lawn.

9. 2 Mi to Marina & Lake Cumberland! Newly Built Home

2 Mi to Marina & Lake Cumberland! Newly Built Home
3.0 star property
Somerset
$370 nightly
The price is $408
Nov 30 - Dec 1
Total with taxes and fees
2 Mi to Marina & Lake Cumberland! Newly Built Home
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Monticello Hotel Reviews

Best Western Lake Cumberland Inn

Best Western Lake Cumberland Inn

10/10 Excellent
"We ALWAYS stay here when we travel from Indiana to Monticello to visit family. I wouldn’t go anywhere else. The staff are the nicest most helpful people. Now, their breakfast is gross. Eggs are fake, bacon is 🤮 (probably also fake). Their waffles are good though. But for someone who has diabetes we need the protein."
Julia 2-night trip
Posted 1 hour ago
Best Western Lake Cumberland Inn

Find out more about Monticello

Monticello Cottages information

Number of reviews
313
Accommodation
144 Cottages
Lowest Price
$274
Highest Price
$754

Frequently asked questions

How much do cottages in Monticello cost?
Cottages in Monticello range between $274 and $754 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.

Explore a world of travel with Expedia