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Compare 256 Vacation Homes in Monticello with updated reviews, rates, and availability.

Boating Mecca: Near Dale Hollow Lake & Golf!

The price is SAR 230
SAR 574 total
includes taxes & fees
5 Jan - 6 Jan
Boating Mecca: Near Dale Hollow Lake & Golf!

River-View Somerset Home: Large Deck, Fire Pit!

9.6 out of 10, Exceptional, (22)
"Wow. This is a gem in Pulaski. The views of Cumberland are amazing and the sunsets were breathtaking. "
River-View Somerset Home: Large Deck, Fire Pit!

LOG Cabin, 5 miles from town, but very country setting

9.6 out of 10, Exceptional, (84)
"Veru nice ..clean .. in a quite area .. overall good. "
LOG Cabin, 5 miles from town, but very country setting

6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍

9.8 out of 10, Exceptional, (20)
"My family of nine and I had a great time and plenty of room. The views are incredible. The toys including pool table and foosball were used heavily. The hot tub was very comfortable and easy to use. There were a couple of unexpected bonuses including an extra refrigerator in the garage which was very helpful for all the food we needed for Thanksgiving, and secondly that they had two sets of washers and dryers which was very helpful for a large group. The second flat parking pad beyond the pool...
6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍

Little blue house on the lake

9.6 out of 10, Exceptional, (11)
"Place was great! Place was clean upon arrival with great communication with property owner. Would definitely recommend! Thanks for the stay!"
Little blue house on the lake

Near Cumberland River, 12 miles from Wolf Creek Dam, in Creelsboro community

9.6 out of 10, Exceptional, (45)
"House was perfect for the 4 adults and 1 child we had with us, big yard for the dogs and it was a 5 minute drive to the nearest boat ramp on the cumberland river."
Near Cumberland River, 12 miles from Wolf Creek Dam, in Creelsboro community

Lake Cumberland Ohana. Kid friendly, best views, hot tub.

9.4 out of 10, Exceptional, (3)
"The house was perfect for a lake trip. Only issue was there was one less bed than pictured, but we made it work and loved the house. Robert was a great communicator and answered all my questions within minutes. Would highly recommend staying here!"
Lake Cumberland Ohana. Kid friendly, best views, hot tub.

Hideaway 27

10.0 out of 10, Exceptional, (23)
"All was great"
The price is SAR 406
SAR 914 total
includes taxes & fees
9 Jan - 10 Jan
Hideaway 27

Charming 1-bedroom fish shack in Somerset with WiFi and AC

2.0 star property
10.0 out of 10, Exceptional, (4)
"Small gathering for Christmas .. small but plenty of room on porch and outside if good weather for extra space Robe in the bathroom .. washer/dryer combo Record player in the bedroom .. will try it next time Great host Can’t wait to book again "
The price is SAR 432
SAR 559 total
includes taxes & fees
4 Jan - 5 Jan
Charming 1-bedroom fish shack in Somerset with WiFi and AC

Lake Retreat at Lake Cumberland Resort

9.6 out of 10, Exceptional, (164)
"Lovely stay in your comfortable and clean cabin for our family Thanksgiving stay. The home is a little off the beaten bath but definitely quiet and safe area with lots of trails to explore nearby. Well stocked home and great communication with the hosts. Thank you for everything."
Lake Retreat at Lake Cumberland Resort

Lakeside Hideaway I - newly renovated lakefront with hot tub / walk to boat ramp

9.8 out of 10, Exceptional, (42)
"We enjoyed our stay very much. The property itself was bigger than we expected for the cost. It was very clean and was stocked with anything we needed. The bed was comfortable. We enjoyed spending time on the covered porch and in the hot tub. I would definitely stay there again, and would highly recommend it."
Lakeside Hideaway I - newly renovated lakefront with hot tub / walk to boat ramp

Lake and Mountain Views

9.8 out of 10, Exceptional, (61)
"Cabin is great and has view of the lake. Sitting on the deck is so relaxing with a cup of coffee since we are there over Thanksgiving. Patricia is great to work with and responds quickly. Will be back next year."
Lake and Mountain Views

Ellie’s Place - Woodsy Retreat! Book now and enjoy.

9.8 out of 10, Exceptional, (119)
"The owner thought of everything for this nice cabin! Games, hot tub and well stock with thibgs you might need. The area was very quiet"
Ellie’s Place - Woodsy Retreat! Book now and enjoy.

Lake house with boat ramp access across the street & tons of boat parking space.

9.8 out of 10, Exceptional, (66)
"I cannot say enough wonderful things about our stay. The house is beautiful, we had so much room for our whole family and the kids thoroughly enjoyed the basement. The location was perfect for our needs. All of us just loved the house, we didn’t want to leave and will definitely be back! Thank you so much!"
Lake house with boat ramp access across the street & tons of boat parking space.

Dale Hollow Lake getaway tucked in the woods, one minute from the lake!

10.0 out of 10, Exceptional, (47)
"good to have breakfast on the back patio and watch the humming birds"
Dale Hollow Lake getaway tucked in the woods, one minute from the lake!

Cozy Lake Cumberland Lakeview Shangri-la

9.8 out of 10, Exceptional, (9)
"We all had a wonderful time. Setting is beautful and the house is very nice. We loved the hot tub in the evenings. "
The price is SAR 732
SAR 1,631 total
includes taxes & fees
2 Feb - 3 Feb
Cozy Lake Cumberland Lakeview Shangri-la

Remodeled House Near Jamestown Marina, Room to Park Your Boat in Driveway!

9.8 out of 10, Exceptional, (10)
"House has everything you need. It’s close distance to the marina. We enjoyed our stay."
The price is SAR 676
SAR 1,561 total
includes taxes & fees
4 Jan - 5 Jan
Remodeled House Near Jamestown Marina, Room to Park Your Boat in Driveway!

Cumberland Get-A-Way located at entrance of State Park

10.0 out of 10, Exceptional, (14)
"The location was very convenient to the State Park Marina. The area was very pretty and felt secluded. Some of us took advantage of the fishing pond. We had a group of 19 and there was plenty of room for all. The only issue we had was the hot tub was not functioning, It would have been nice, but did not take away from our enjoyment of our weekend. We would definitely stay here again!"
Cumberland Get-A-Way located at entrance of State Park

“Lakeview Retreat” - Lakeview with Public dock bottom of hill/Free Launch

10.0 out of 10, Exceptional, (14)
"As usual, the property was extremely clean and well maintained. One of our favorite places to stay when we are in town. "
“Lakeview Retreat” - Lakeview with Public dock bottom of hill/Free Launch

Vacationers' Delight at Conley Bottom

10.0 out of 10, Exceptional, (50)
"We wanted a nice place close to the lake and this was exactly what we was looking for to be able to go boating every day."
Vacationers' Delight at Conley Bottom
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

6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍

9.8 out of 10, Exceptional, (20)
"My family of nine and I had a great time and plenty of room. The views are incredible. The toys including pool table and foosball were used heavily. The hot tub was very comfortable and easy to use. There were a couple of unexpected bonuses including an extra refrigerator in the garage which was very helpful for all the food we needed for Thanksgiving, and secondly that they had two sets of washers and dryers which was very helpful for a large group. The second flat parking pad beyond the pool...
6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍

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

9.8 out of 10, Exceptional, (144)
"Thank you for hosting us. Everything was great."
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, (104)
"We enjoyed sitting on the screened-in patio overlooking the river watching the falling leaves float to the ground. Watched a group of 15 wild turkeys make the way way past the property. their wwa"
Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!
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.