Photo by Lisa Klein

Search Monticello Cottage Rentals from CA $134

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Browse Select Monticello Cottages

The Blue Heron Farm Cottage ~ Big South Fork ~ Relax on Five Private Acres!
2 bedrooms, WiFi, bed sheets
The Blue Heron Farm Cottage ~ Big South Fork ~ Relax on Five Private Acres!
9.6 out of 10, Exceptional, (4)
"We were looking for somewhere that was centrally located to local hiking & attractions, this cabin was within 20 mins to a bunch of hiking spots. I was worried that we'd have trouble with a our baby's pack n play but the primary bedroom had a giant closet attached that worked perfectly as a nursery. The cottage itself was very clean & adorably decorated. The only bummer was the horses weren't there but we did get some deer visitors!"
The Blue Heron Farm Cottage ~ Big South Fork ~ Relax on Five Private Acres!
Lake Front Home with community boat ramp. Private, close to marinas and town.
Dining
Lake Front Home with community boat ramp. Private, close to marinas and town.
9.6 out of 10, Exceptional, (209)
"Very clean, spacious, quiet, clean place! Just like your pictures & description! That part of the lake was quiet & view priceless if you love nature. Close by shopping, the falls etc. Loved it & will be back again! Linda was great too!"
Lake Front Home with community boat ramp. Private, close to marinas and town.
NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking
View from property
NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking
10.0 out of 10, Exceptional, (27)
"We had an amazing time on the lake. The house was decorated beautifully! We had an amazing view and loved sitting outside on the back covered patio! Very happy with everything! "
NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking
Boating Mecca: Near Dale Hollow Lake & Golf!
Terrace/patio
Boating Mecca: Near Dale Hollow Lake & Golf!
10.0 out of 10, Exceptional, (65)
"Good location for our needs, and snacks were a plus! Ty! "
Boating Mecca: Near Dale Hollow Lake & Golf!
Harbor Hideway is a cozy, romantic gem minutes away from Jamestown Marina!
Property grounds
Harbor Hideway is a cozy, romantic gem minutes away from Jamestown Marina!
10.0 out of 10, Exceptional, (8)
"The property was very clean and a few minutes from Jamestown Marina. Plenty of parking for 2 trucks and a 40 ft. boat/trailer. We stayed for the poker run and had an amazing time."
The price is CA $232
CA $546 total
includes taxes & fees
Oct 1 - Oct 2
Harbor Hideway is a cozy, romantic gem minutes away from Jamestown Marina!
Relaxing Lakefront Getaway Near Marina, Park, & Town
Property grounds
Relaxing Lakefront Getaway Near Marina, Park, & Town
10.0 out of 10, Exceptional, (140)
"We enjoyed our stay at this location, Everything was clean an in order."
The price is CA $149
CA $341 total
includes taxes & fees
Sep 30 - Oct 1
Relaxing Lakefront Getaway Near Marina, Park, & Town
Cozy Cumberland Cottage
Property grounds
Cozy Cumberland Cottage
9.8 out of 10, Exceptional, (88)
"We usually spend our annual family vacation at Lake Cumberland, when we do we always rent the Cozy Cumberland Cottage"
Cozy Cumberland Cottage
Renovated Cottage! Overlooks Dale Hollow!
Microwave, oven, stovetop, dishwasher
Renovated Cottage! Overlooks Dale Hollow!
9.8 out of 10, Exceptional, (59)
"Very comfortable and cozy holiday getaway. Gorgeous view of the lake and peaceful setting. "
Renovated Cottage! Overlooks Dale Hollow!
A true guest favorite! Super clean! Close to everything!
Property grounds
A true guest favorite! Super clean! Close to everything!
10.0 out of 10, Exceptional, (8)
"Rebecca went out of her way to make us feel comfortable. The house is clean and well stocked. Close to the lake. Perfect getaway!"
The price is CA $134
CA $314 total
includes taxes & fees
Sep 30 - Oct 1
A true guest favorite! Super clean! Close to everything!
Byrdstown Cabin - w/ Fire Pit, Near Marina & Lake!
Interior
Byrdstown Cabin - w/ Fire Pit, Near Marina & Lake!
3.0 star property
8.0 out of 10, Very good, (1)
"The only thing I didn’t like was there isn’t really a good place to turn around if you have a boat. "
Byrdstown Cabin - w/ Fire Pit, Near Marina & Lake!
Cozy cabin minutes from Lake Cumberland with room for your boat.
Fridge, microwave, oven, stovetop
Cozy cabin minutes from Lake Cumberland with room for your boat.
10.0 out of 10, Exceptional, (19)
"Enjoyed the peace and quiet. Very clean and well maintained. Enjoyed watching the wildlife. "
Cozy cabin minutes from Lake Cumberland with room for your boat.
This charming cozy cottage has a private hot tub, deck for fishing.
Property grounds
This charming cozy cottage has a private hot tub, deck for fishing.
9.8 out of 10, Exceptional, (137)
"Nice little cottage in a quiet, friendly neighborhood. The place was very clean and had everything you need to cook dinner or cookout. The hot tub was amazing and we found the pond very relaxing. Great location close to Lake Cumberland 9 minutes from Conley Bottom Marina. "
This charming cozy cottage has a private hot tub, deck for fishing.
Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!
Exterior
Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!
10.0 out of 10, Exceptional, (9)
"This vacation rental is awesome! It had everything we needed for a relaxing vacation. The hot tub was very clean and well kept. The owner was very responsive and even let us check in early. Definitely recommend!!! "
Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!
The Lakeside Escape Cumberland
Terrace/patio
The Lakeside Escape Cumberland
10.0 out of 10, Exceptional, (5)
"The house has plenty of space and was very comfortable, we really enjoyed the screened porch. Michelle is very helpful and friendly!"
The Lakeside Escape Cumberland
Lake Cumberland Eclectic Retreat: Fire Pit + Views
Microwave, cookware/dishes/utensils, spices, dining tables
Lake Cumberland Eclectic Retreat: Fire Pit + Views
10.0 out of 10, Exceptional, (13)
"This property was very beautiful, spacious, and clean. It was very comfortable for my family. The owner was very helpful and took care of any issues with great efficiency. "
Lake Cumberland Eclectic Retreat: Fire Pit + Views
Luxury Cottage with pool, Less than 2 miles from Jamestown Marina!!
Exterior
Luxury Cottage with pool, Less than 2 miles from Jamestown Marina!!
10.0 out of 10, Exceptional, (18)
"Will definitely stay here again "
Luxury Cottage with pool, Less than 2 miles from Jamestown Marina!!
Luxury Cottage with pool, Less than 2 miles from Jamestown Marina!! -#2
Exterior
Luxury Cottage with pool, Less than 2 miles from Jamestown Marina!! -#2
10.0 out of 10, Exceptional, (14)
"Cottage is right outside of Jamestown KY. You are close to lake Cumberland and also close to Jamestown. Cottage is beautiful and very spacious. Cottage comes with everything you could need during your stay. We will definitely be back! "
Luxury Cottage with pool, Less than 2 miles from Jamestown Marina!! -#2
Cozy cottage nestled in the woods bordering beautiful Lake Cumberland
Property grounds
Cozy cottage nestled in the woods bordering beautiful Lake Cumberland
8.4 out of 10, Very good, (15)
"The stay was good! The beds were so comfortable and my family enjoyed playing the games at night while we were calming down for bed. The cabin was clean and pretty well stocked. I would like to suggest a regular coffee pot as the Keirug coffee is very weak. "
Cozy cottage nestled in the woods bordering beautiful Lake Cumberland
Lake Daze, Blue Cottage <1mile to Jamestown Marina with space to trailer boat.
Smart TV
Lake Daze, Blue Cottage <1mile to Jamestown Marina with space to trailer boat.
9.6 out of 10, Exceptional, (25)
"Clean & decor was nice, had everything we needed, warm house, easy checkin, tv was nice & kitchen was nice, location not far from town, need to clean up wood in back yard & work on driveways, favorite parts were lights on front deck (few bulbs need replaced)& bathroom tile in the shower was beautiful"
The price is CA $204
CA $468 total
includes taxes & fees
Sep 24 - Sep 25
Lake Daze, Blue Cottage <1mile to Jamestown Marina with space to trailer boat.
Country Cottage < 3 Mi to Dale Hollow Lake!
Exterior
Country Cottage < 3 Mi to Dale Hollow Lake!
9.2 out of 10, Wonderful, (30)
"We enjoyed our stay in this very clean and up-to-date cottage!! The outside porch was not very clean but liked having the gate so our small dog could enjoy it with us while we had our morning coffee!! Found it extremely difficult to get our pontoon in to unload!! Gates are not wide enough to manage getting boats in and out easily! "
Country Cottage < 3 Mi to Dale Hollow Lake!
Don't see what you're looking for?
See all available properties in Monticello
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Monticello

This charming cozy cottage has a private hot tub, deck for fishing.
Property grounds
This charming cozy cottage has a private hot tub, deck for fishing.
9.8 out of 10, Exceptional, (137)
"Nice little cottage in a quiet, friendly neighborhood. The place was very clean and had everything you need to cook dinner or cookout. The hot tub was amazing and we found the pond very relaxing. Great location close to Lake Cumberland 9 minutes from Conley Bottom Marina. "
This charming cozy cottage has a private hot tub, deck for fishing.
Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!
Property grounds
Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!
10.0 out of 10, Exceptional, (101)
"Never been to KY came for a family reunion & needed a home base. We had 2 teens & a 6 year old plus 4 adults & the space was perfect. Everyone loved the the game room & ping pong. Screened porch was fab didn’t use the fire pits since we were gone most of the time. Kitchen had all we needed. Only thing I would highly suggest is make a path down to the lake for access. Wonderful views but no way to get to the water! "
Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!
Tinyhouse LakeView Cottage with a MILLION DOLLAR VIEW!! ATV trail to lake!
Property grounds
Tinyhouse LakeView Cottage with a MILLION DOLLAR VIEW!! ATV trail to lake!
10.0 out of 10, Exceptional, (37)
"Had a wonderful time here! The view is perfect. Holly was a great host, i didnt need to ask her for anything. Clean and decorated and a wonderful escape!clean"
Tinyhouse LakeView Cottage with a MILLION DOLLAR VIEW!! ATV trail to lake!
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.

Frequently asked questions

How much do cottages in Monticello cost?
You can expect to pay between CA $134 and CA $232 per night for cottages in Monticello. Whatever your budget, a fantastic stay is only clicks away on Expedia. 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?
Booking a cottage in Monticello is as simple as working out your travel dates and picking your ideal place for a getaway in the outdoors. From chic retreats to inexpensive properties and cottages that offer perks like a pool, Expedia has something for all traveler styles. As for terrific deals? We’ve have them as well!
How can I find cheap cottages in Monticello?
The easiest way to track down cheap cottages in Monticello is with Expedia’s convenient filter tool. Tailor your search results by amenities, budget and star rating to take advantage of awesome prices with only a few clicks.
What is there to do in Monticello near my cottage?
After you’ve unpacked and settled in, set out and discover the incredible things Monticello has for you to experience. Lake Cumberland Winery is a popular attraction to add to your travel itinerary.