Photo by Lisa Klein

Monticello Vacation Rentals

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Browse Select Monticello Vacation Homes

Cozy Gray House
10.0 out of 10, Exceptional, (52)
"Great place to stay . Clean, convenient to town and easy to get to. I’m an Elder of Brushcreek chapter Bikers for Christ and I was impressed that you had a Bible there!"
The price is CA $141
CA $250 total
includes taxes & fees
Sep 28 - Sep 29
Cozy Gray House
Located on the picturesque shores of Lake Cumberland.
9.0 out of 10, Wonderful, (2)
"It was not clean by no means. 1st the sheets looked like they hadn't been changed /washed ins while. The refrigerator was dirty,"
Located on the picturesque shores of Lake Cumberland.
Lake Retreat at Lake Cumberland Resort
9.6 out of 10, Exceptional, (159)
"Booked this property to have one last summer retreat with the family. The location is very private. There is one neighbor close by, but the position of the home was such that we were not too close. The home has just about everything you need. The kitchen is well supplied. The screened porch was fantastic. Everyone enjoyed the hot tub and the fire pit. You can purchase bundles of wood at Davis grocery nearby. A boat ramp is just over the hill. The only con would be if you were traveling with...
Lake Retreat at Lake Cumberland Resort
Lake Cumberland Hideaway #1-2 miles from Jtown Marina! Boat Parking & Fire Pit!
10.0 out of 10, Exceptional, (150)
"We all had a great time at this property! Everything was as advertised and the host couldn't have been more hospitable! We hope to stay here again in the future. Thank you"
Lake Cumberland Hideaway #1-2 miles from Jtown Marina! Boat Parking & Fire Pit!
Pool / Grill, Dale Hollow Lake and nearby Sunset Marina with Mountain view
9.6 out of 10, Exceptional, (102)
"We have loved coming to visit with you guys for several years now. This property has a little bit of something for everyone. The beautiful pool, picturesque atmosphere, and the feeling of being right at home is exactly what you want when you’re spending time with your family. The host is always very friendly and welcoming, very responsive to any and all needs as they may arise. We have always been very pleased with our stay and will continue to visit in the future."
Pool / Grill, Dale Hollow Lake and nearby Sunset Marina with Mountain view
1-Mile from Conley Bottom's ramp
9.8 out of 10, Exceptional, (30)
"Great location if you are boating from Conley Bottom. Cute place. Well stocked. Beds could be more comfortable but overall a great place to stay. "
1-Mile from Conley Bottom's ramp
LOG Cabin, 5 miles from town, but very country setting
9.6 out of 10, Exceptional, (83)
"Enjoyable getaway for our family with no issues whatsoever. We had a great time!"
LOG Cabin, 5 miles from town, but very country setting
Lakeview Happy Place - 10 Person Home W/ Hot Tub! 🤙
10.0 out of 10, Exceptional, (68)
"The house was very clean. The kitchen was well stocked with everything needed to prepare meals. The view was amazing. The location was very convenient to marinas and stores."
The price is CA $315
CA $694 total
includes taxes & fees
Sep 30 - Oct 1
Lakeview Happy Place - 10 Person Home W/ Hot Tub! 🤙
"Shore Thing", Cozy Lake Cumberland Cabin - Hot Tub, Fire Pit, Minutes from Lake
8.2 out of 10, Very good, (12)
"The cabin was very secure and clean. I was surprised at how tiny the entry door was! The loft has a very low ceiling and the shower head is very low making it difficult for someone tall to shower. It smelled of natural gas when we arrived and I realized some had left the gas stove burner on! Overall it was a great, cozy stay and was fine for 2 people. It had everything we needed! Would stay again!"
"Shore Thing", Cozy Lake Cumberland Cabin - Hot Tub, Fire Pit, Minutes from Lake
Russell Springs Getaway, 10 Mi to Lake Cumberland!
10.0 out of 10, Exceptional, (6)
"The place was clean and fully stocked with all the household needs. The beds and family room furniture were comfortable. The house is well insulated with little to no road noise. The host left us a delicious cake and fresh farm eggs. A clothes line or dryer would have been nice for large beach towels. Overall we had a wonderful stay and hope to book the property again soon!"
Russell Springs Getaway, 10 Mi to Lake Cumberland!
Four Bed Cumberland River House With Private Boat Launch
9.6 out of 10, Exceptional, (18)
"Great"
Four Bed Cumberland River House With Private Boat Launch
Spacious 4-BR house w/ wraparound porch, fire pit area and hot tub -Sleeps 18-20
2.0 star property
Spacious 4-BR house w/ wraparound porch, fire pit area and hot tub -Sleeps 18-20
Driftwood Cottage Lake Cumberland Retreat with hot tub and private dock!
9.4 out of 10, Exceptional, (3)
"The house was adorable very spacious clean and had most of everything you would need. The only little complaint i would have is that the fireplace was out of gas which was a little bit of a bummer."
Driftwood Cottage Lake Cumberland Retreat with hot tub and private dock!
Lakeside Hideaway II - lakefront with hot tub / walk to boat ramp
10.0 out of 10, Exceptional, (32)
"We had a wonderful stay and enjoyed your rental. We love your rental and we’re so happy to get to use it once again. The facility is well equipped, very clean, decorated beautifully and conveniently located. We look forward to visiting again in the future! "
Lakeside Hideaway II - lakefront with hot tub / walk to boat ramp
LAKE FRONT CABIN with Large Deck.
10.0 out of 10, Exceptional, (28)
"Cleanest rental I’ve ever stayed in. Centrally located between the city and the lake. Plenty of space to spread out and the deck was a nice feature."
LAKE FRONT CABIN with Large Deck.
Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!
9.8 out of 10, Exceptional, (25)
"We had an enjoyable stay. Excellent communication with the owners, property had all we needed and more. Great location, ample parking and perfect size dock to anchor our boat to and play off of. Only con, as others mentioned, was the steep trail down to the water. Requires proper footwear and stability. Wasn’t an issue for us since we’re all adults in decent shape. We didn’t have young ones or elderly people with us."
Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!
Spacious 5-Bedroom Home on Lake Cumberland!
10.0 out of 10, Exceptional, (7)
"We had a wonderful weekend! This is a beautiful space. That master bedroom is incredible!! 5-Star!!"
Spacious 5-Bedroom Home on Lake Cumberland!
Idyllic Bronston Retreat w/ Fire Pit + View!
9.0 out of 10, Wonderful, (12)
"plenty of room to park 3 cars and 2 boat trailers. also, hostess was most responsive vrbo person I have ever dealt with"
Idyllic Bronston Retreat w/ Fire Pit + View!
Waterfalls, fishing pond, lake view, vast property
10.0 out of 10, Exceptional, (16)
"Great house for the weekend! fishing in the pond, kayaked from boat ramp to waterfall, hiked from property to waterfall, ate in Somerset & Columbia, comfortable bed upstairs, great views of nature. Couldnt get charcoal grill hot enough to cook the steaks with what little coals were left, kitchen window doesnt lock and upstairs bath leaks into downstairs bedroom."
Waterfalls, fishing pond, lake view, vast property
Lakeside Hideaway I - newly renovated lakefront with hot tub / walk to boat ramp
9.8 out of 10, Exceptional, (39)
"Everything was excellent! Thank you. "
Lakeside Hideaway I - newly renovated lakefront with hot tub / walk to boat ramp
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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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Other property types in Monticello

This charming cozy cottage has a private hot tub, deck for fishing.
9.8 out of 10, Exceptional, (138)
"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!
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!
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.