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Compare 270 Vacation Homes in Monticello with updated reviews, rates, and availability.

Beautiful "Harborview at Lake Cumberland" overlooking Lee's Ford Marina.

Beautiful "Harborview at Lake Cumberland" overlooking Lee's Ford Marina.

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

9.8 out of 10, Exceptional, (67)
"Our third year at this location for our family and friends get together. Great location. Perfect for our event! Thanks to the host for all the preparations. Highly satisfied and will very likely use the same property again next year. "
Lake house with boat ramp access across the street & tons of boat parking space.

4 Bedrooms, Private pool, hot tub, Game room, and Water Front View!

9.6 out of 10, Exceptional, (88)
"Check in was easy. Very nice place. Plenty of room to visit with family. Would be very enjoyable in the summer when the pool is open. My grandson enjoyed the basketball game. Two drawbacks. First, we had 5 people who needed to shower in the morning, hot water was nearly depleted by the third so the last two took cool showers. The other is the driveway is STEEP, so taking the trash out was a nice workout!! Otherwise we enjoyed the property and would consider returning."
4 Bedrooms, Private pool, hot tub, Game room, and Water Front View!

LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY

10.0 out of 10, Exceptional, (127)
"Was everything we were looking for. The view was amazing. The local was close to stores and restaurants. The home had everything we needed. "
LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY

Prather Place, Spacious, Deck And View, Entertaining Basement, Minutes to Marina

10.0 out of 10, Exceptional, (139)
"The house was exactly as described. Our family enjoyed the basement game room/ movie room the most. There were a couple things that would have made it better but was definitely out of the owners hands. The bridge was out so if you needed anything from Somerset, it took 30 minutes to get to instead of 5 minutes. The organization of the kitchen utensils (pots, pans, appliances, etc.) could definitely use some work. But overall, we enjoyed our stay and would recommend this place to anyone who...
Prather Place, Spacious, Deck And View, Entertaining Basement, Minutes to Marina

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 675
SAR 1,551 total
includes taxes & fees
11 Mar - 12 Mar
Remodeled House Near Jamestown Marina, Room to Park Your Boat in Driveway!

Calming 1-bedroom yellow door house close to lake with Wi-Fi, AC

2.0 star property
The price is SAR 413
SAR 538 total
includes taxes & fees
12 Mar - 13 Mar
Calming 1-bedroom yellow door house close to lake with Wi-Fi, AC

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!

Lake Retreat at Lake Cumberland Resort

9.8 out of 10, Exceptional, (168)
"We had a wonderful stay at your cabin! Was very cozy, clean and comfortable. We loved the hot tub! Will stay again in the future. "
Lake Retreat at Lake Cumberland Resort

⚓ Anchor Down ⚓ Spacious lakefront home on Lake Cumberland - W/ PRIVATE SLIP!

9.8 out of 10, Exceptional, (17)
"Home is one of the nicest, best decorated, best kept and best stocked rentals possible! Owners have done a wonderful job and attended to the smallest details to make their guests comfortable. All the comforts of home are included in this property and owners communicate well. It is close to dock where they provide a boat slip and the experience of sitting is the ample furnishings on porch or in the living room to see one of the best lake views simply cannot be beat!"
The price is SAR 2,814
SAR 4,016 total
includes taxes & fees
12 Mar - 13 Mar
⚓ Anchor Down ⚓ Spacious lakefront home on Lake Cumberland - W/ PRIVATE SLIP!

Amazing 5BR House with Lake & Mountain Views in Gated Resort

10.0 out of 10, Exceptional, (85)
"We loved staying in this home, and with 3 generations, it was well suited to our needs. The kitchen was very well stocked and made it easy to do all our holiday baking. The five bedrooms and 5 1/2 baths meant that everyone had their privacy. The views of the river made for a perfect setting. We hope to return again in the future. "
Amazing 5BR House with Lake & Mountain Views in Gated Resort

Lake-Front Woodson Bend 14-1

9.8 out of 10, Exceptional, (163)
"The condo was absolutely perfect. It had everything we needed in an absolute perfect setting. The community is amazing! The bed was the most comfortable bed I have ever had in any VRBO. "
Lake-Front Woodson Bend 14-1

Boating Mecca: Near Dale Hollow Lake & Golf!

10.0 out of 10, Exceptional, (67)
"Couldn't have ask for a nicer place or better host. Everything was great except for the weather! I'm sure it will be better next time. Thanks"
The price is SAR 270
SAR 625 total
includes taxes & fees
12 Mar - 13 Mar
Boating Mecca: Near Dale Hollow Lake & Golf!

Welcome to “Lakeview Paradise” – Your Perfect Lakeside Escape

10.0 out of 10, Exceptional, (16)
"Pros: This house was large, we went as a party of 10 and had plenty of space. There were 3 sitting rooms with TVs and an additional without that overlooked the lake, so there were plenty of spaces to spread out when the weather forced us in. The kitchen has plenty of storage space and worked well for preparing meals for a large group.The hot tub was large, fitting 2 adults, 3 teens, and 3 kids fine. It was also in a covered area along with a gas fireplace, so those things could be used in rainy...
Welcome to “Lakeview Paradise” – Your Perfect Lakeside Escape

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

2.0 star property
10.0 out of 10, Exceptional, (6)
"Very nice and clean! "
The price is SAR 469
SAR 600 total
includes taxes & fees
11 Mar - 12 Mar
Captivating 2-bedroom, garage door house with WiFi, AC in welcoming Somerset

Centrally located house at Pond Meadow Place

9.6 out of 10, Exceptional, (33)
"I would have given it a five-star rating if it had just a few minor changes. Having something to put your suitcase on in every room or dressers, a dishwasher that felt secure to use, and a place in each bathroom to hang your towels and place your shampoo and soap."
Centrally located house at Pond Meadow Place

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

DRIFT INN just 10 minutes from Jamestown Marina

10.0 out of 10, Exceptional, (7)
"Good"
DRIFT INN just 10 minutes from Jamestown Marina

Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!

9.8 out of 10, Exceptional, (29)
"The property was excellent and the family had a great time "
Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!

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!😍
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, (145)
"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.

4 Bedrooms, Private pool, hot tub, Game room, and Water Front View!

9.6 out of 10, Exceptional, (88)
"Check in was easy. Very nice place. Plenty of room to visit with family. Would be very enjoyable in the summer when the pool is open. My grandson enjoyed the basketball game. Two drawbacks. First, we had 5 people who needed to shower in the morning, hot water was nearly depleted by the third so the last two took cool showers. The other is the driveway is STEEP, so taking the trash out was a nice workout!! Otherwise we enjoyed the property and would consider returning."
4 Bedrooms, Private pool, hot tub, Game room, and Water Front View!

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.