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Search Vacation Homes in Monticello

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Compare 260 Vacation Homes in Monticello with updated reviews, rates, and availability.

Pool / Grill, Dale Hollow Lake and nearby Sunset Marina with Mountain view

9.6 out of 10, Exceptional, (104)
"This property was just the right size for 4 adults and 3 teenagers. We had one good day of weather and spent it on the lake, however, the girls would have loved some pictures by the pool—it looked as if maybe it was in the process of being drained and then just left. It was green and not covered for winter yet. There is a nice fire pit area that we took advantage of several nights. Bring your own chairs! The driveway is a little narrow, but has ample parking. The only other “issue” we had was...
Pool / Grill, Dale Hollow Lake and nearby Sunset Marina with Mountain view

Cozy Gray House

10.0 out of 10, Exceptional, (56)
"Adorable property. Reasonable cost. Great location for hiking Big South Fork and running into Oneida for ice cream at Mary Belles. We adored the local, well cared for beautiful stray dog named Buddy. Our only complaint is we couldnt work it out to stay longer "
The price is SAR 394
SAR 697 total
includes taxes & fees
1 Dec - 2 Dec
Cozy Gray House

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

9.8 out of 10, Exceptional, (19)
"Overall we enjoyed our stay here, bummed that the pool was not open as it showed in the description of the house and was the main reason for choosing the location. If it is closed for the season, list it as such. The view is great! "
6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍

Wet Feet Retreat is a family friendly home near Burnside Island State Park.

10.0 out of 10, Exceptional, (57)
"Live staying here , have stayed several times now, very nice ! Will return"
Wet Feet Retreat is a family friendly home near Burnside Island State Park.

"Shore Thing", Cozy Lake Cumberland Cabin - Hot Tub, Fire Pit, Minutes from Lake

8.4 out of 10, Very Good, (16)
"Great place to getaway for peace and quiet!"
"Shore Thing", Cozy Lake Cumberland Cabin - Hot Tub, Fire Pit, Minutes from Lake

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.

Russell Springs Getaway, 10 Mi to Lake Cumberland!

10.0 out of 10, Exceptional, (8)
"The host was remarkable in communication and hospitality. We were created with hand written note, fresh farm eggs and a homemade chocolate cake. Would recommend this property and host to anyone looking for southern hospitality and clean property for their stay. "
Russell Springs Getaway, 10 Mi to Lake Cumberland!

Captivating 2-bedroom, garage door house with WiFi, AC in welcoming Somerset

2.0 star property
10.0 out of 10, Exceptional, (1)
The price is SAR 357
SAR 476 total
includes taxes & fees
30 Nov - 1 Dec
Captivating 2-bedroom, garage door house with WiFi, AC in welcoming Somerset

Lake Retreat at Lake Cumberland Resort

9.6 out of 10, Exceptional, (163)
"We stayed for a long weekend with our teens. Nice area, plenty of space for our family, good WiFi and things to do. We found the musty odor of the home unpleasant, that isn't totally uncommon with rentals and the change of seasons. Unfortunately we were only able to use the hot tub once before it started to have issues. Andrew was very attentive to our concerns but it did spoil some of our fun. Andrew was a good host!"
Lake Retreat at Lake Cumberland Resort

Lakeside Hideaway II - lakefront with hot tub / walk to boat ramp

10.0 out of 10, Exceptional, (34)
"Such an amazing place to enjoy time with family!"
Lakeside Hideaway II - lakefront with hot tub / walk to boat ramp

LAKE FRONT CABIN with Large Deck.

10.0 out of 10, Exceptional, (29)
"We had a great experience with this stay! The cabin was immaculate! Had what we needed and not too much! The property manager communicated all information needed and was so gracious!!! "
LAKE FRONT CABIN with Large Deck.

Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!

9.8 out of 10, Exceptional, (27)
"Great location. Great place, beautiful views"
Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!

Joy On The Lake · Cumberland Canvas: Lake Views, Fire Pit, Pets OK

10.0 out of 10, Exceptional, (7)
"This was just what we needed! Beautiful sunset! Billiard and karaoke fun!!"
The price is SAR 751
SAR 1,705 total
includes taxes & fees
3 Dec - 4 Dec
Joy On The Lake · Cumberland Canvas: Lake Views, Fire Pit, Pets OK

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, (59)
"Nice little cabin, very Homie had everything you would want in it. We would probably stay there again."
Lake and Mountain Views

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!

Welcome to “Lakeview Paradise” – Your Perfect Lakeside Escape

10.0 out of 10, Exceptional, (13)
"The home was very spacious, our group of 9 had more than enough private and communal areas that we were always comfortable. The hot tub and fire pit on the screened porch were a hit. Would stay again!"
Welcome to “Lakeview Paradise” – Your Perfect Lakeside Escape

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
30 Nov - 1 Dec
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 1,557 total
includes taxes & fees
1 Dec - 2 Dec
Remodeled House Near Jamestown Marina, Room to Park Your Boat in Driveway!

Luxe Lake Barndo w/ 2 King Suites! Hot Tub, Fire Pit, 1/8 mile to boat ramp!

10.0 out of 10, Exceptional, (12)
"This property was such a dream. We came down for a few nights with our friends, kids, and pups and everything was perfect for our entire group. The outdoor entertaining space was big enough for everyone to hang out and afternoon football inside was perfect! We used the huge open concept to let all the kids carve pumpkins. The bathrooms and bedrooms were exactly as described. The nightly fires were so relaxing, and the area was so quiet. We can’t wait to come back! Thanks so much hosts for giving...
The price is SAR 656
SAR 1,272 total
includes taxes & fees
1 Dec - 2 Dec
Luxe Lake Barndo w/ 2 King Suites! Hot Tub, Fire Pit, 1/8 mile to boat ramp!
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, (142)
"Was a great stay. Nice place, deck over a pond. Owner was great communication. highly recommend."
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!

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

9.8 out of 10, Exceptional, (19)
"Overall we enjoyed our stay here, bummed that the pool was not open as it showed in the description of the house and was the main reason for choosing the location. If it is closed for the season, list it as such. The view is great! "
6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍
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.