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Compare 115 Cottages in Monticello with updated reviews, rates, and availability.

Country Cottage < 3 Mi to Dale Hollow Lake!

9.2 out of 10, Wonderful, (30)
"great spot- easy and convenient. Having two bathrooms was the best and everything was clean upon arrival."
Country Cottage < 3 Mi to Dale Hollow Lake!

LAKE CUMBERLAND, FENCED YARD, FIRE PIT, HOT TUB, 100 meg internet, FIREPLACE

10.0 out of 10, Exceptional, (240)
"My wife and I stayed at this house with our dog over New Year’s Eve. It was so cozy, relaxing, and the perfect getaway for our family. The hot tub was great and we loved hiking at the Boone National Forest which was only about 20 minutes from the house. We will definitely be coming back in the future. "
LAKE CUMBERLAND, FENCED YARD, FIRE PIT, HOT TUB, 100 meg internet, FIREPLACE

JAMESTOWN Marina, LCKY. boat parking. pool table. 3 full baths. pet friendly.

10.0 out of 10, Exceptional, (167)
"Wonderful stay!!! House was adorable and as described. The house was very clean and well stocked. Loved the ability to regulate the temperature for each room with the mini split units throughout. Suzanne was excellent host and very detailed in her communication. Thank You for a great stay!"
JAMESTOWN Marina, LCKY. boat parking. pool table. 3 full baths. pet friendly.

Completely remodeled 3 bedroom cottage resort boat dock pool, firepit, game-room

10.0 out of 10, Exceptional, (5)
"Very clean cabin. Great location. Check-in & check-out were super easy!"
Completely remodeled 3 bedroom cottage resort boat dock pool, firepit, game-room

Cottage w/ Deck & BBQ: 2 Mi to Dale Hollow Lake!

10.0 out of 10, Exceptional, (23)
"Great stay!"
Cottage w/ Deck & BBQ: 2 Mi to Dale Hollow Lake!

Lake Front Home with community boat ramp. Private, close to marinas and town.

9.6 out of 10, Exceptional, (218)
"The location was perfect and the description was on point, A beautiful view of the lake and Linda was an amazing host, beautiful relaxing long weekend, we definitely will come back."
Lake Front Home with community boat ramp. Private, close to marinas and town.

This charming cozy cottage has a private hot tub, deck for fishing.

9.8 out of 10, Exceptional, (148)
"We would like to stay there again because of all the amenities the manager was very friendly"
This charming cozy cottage has a private hot tub, deck for fishing.

Serene Lakefront Retreat: Close to Marina, Park, & Downtown Charm

10.0 out of 10, Exceptional, (144)
"We enjoyed our stay at this location, Everything was clean an in order."
Serene Lakefront Retreat: Close to Marina, Park, & Downtown Charm

Renovated Cottage! Overlooks Dale Hollow!

10.0 out of 10, Exceptional, (63)
"Very nice place to stay! "
Renovated Cottage! Overlooks Dale Hollow!

A true guest favorite! Super clean! Close to everything!

10.0 out of 10, Exceptional, (8)
"Very clean and all amenities set up perfectly for our stay. Made a perfect middle ground for visiting mammoth caves and cumberland falls."
A true guest favorite! Super clean! Close to everything!

NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking

10.0 out of 10, Exceptional, (38)
"Our family really enjoyed this place!"
NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking

Lake Cumberland Resort Cabin w/ Community Perks!

3.0 star property
Lake Cumberland Resort Cabin w/ Community Perks!

Restful Rustic Farmhouse on Lake Cumberland

8.8 out of 10, Excellent, (5)
"Nice place. Grill is awesome. Need to clean the gutters but besides that it was perfect for our large group."
The price is AEDĀ 1,653
AEDĀ 2,891 total
includes taxes & fees
3 Jun - 4 Jun
Restful Rustic Farmhouse on Lake Cumberland

Dale Hollow Cottage w/ Covered Porch & Lake Views!

9.8 out of 10, Exceptional, (10)
"Beautiful property and the host thought of every detail a guest might need. Thank you for a wonderful stay!"
Dale Hollow Cottage w/ Covered Porch & Lake Views!

4 Mi to Cumberland River: Cabin w/ Deck & Fire Pit

3.0 star property
4 Mi to Cumberland River: Cabin w/ Deck & Fire Pit

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

9.4 out of 10, Exceptional, (28)
"2nd year here; good location, very nice house, convenient for our needs. Drive is steep and can be slick, less able-bodied people may struggle with stairs to front or log steps to back door, interior is great. "
The price is AEDĀ 735
AEDĀ 1,506 total
includes taxes & fees
3 Jun - 4 Jun
Lake Daze, Blue Cottage <1mile to Jamestown Marina with space to trailer boat.

Pet-Friendly Somerset Cottage Near Boat Ramps!

8.4 out of 10, Very Good, (6)
"Will be back in 2025. Gotta find an area to swim and bank fish. House was cute and fully loaded. All you need is clothes and food.Nice the firewood was there. Campground hostswere really mice "
Pet-Friendly Somerset Cottage Near Boat Ramps!

Woodsy Kentucky Escape w/ Game Room & Lake Access!

3.0 star property
Woodsy Kentucky Escape w/ Game Room & Lake Access!

Cottage at Lake Cumberland; 6m walk to water at Clearwater public boat ramp

10.0 out of 10, Exceptional, (5)
"We stayed here for a fishing tournament. The house was very clean and the hosts quickly communicated when we inquired about adding an additional night. We would definitely stay here again on future Lake Cumberland trips!"
Cottage at Lake Cumberland; 6m walk to water at Clearwater public boat ramp

Family-friendly Lake Cumberland Vacation Rental

3.0 star property
8.6 out of 10, Excellent, (4)
"It was a beautiful Home! We enjoyed our stay very much. The owners were kind and responded quickly with any questions we may have had. Definitely plan on returning! "
Family-friendly Lake Cumberland Vacation Rental
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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Frequently asked questions

How much do cottages in Monticello cost?
Cottages in Monticello range between AED 735 and AED 1,653 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.