Photo by Lisa Klein

Monticello Holiday Rentals

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Holiday Rentals in Monticello

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, (86)
"The location was quiet and like the listing states."
Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!
Tinyhouse LakeView Cottage with a MILLION DOLLAR VIEW!! Kayaks available.
Property grounds
Tinyhouse LakeView Cottage with a MILLION DOLLAR VIEW!! Kayaks available.
10.0 out of 10, Exceptional, (31)
"The property was perfect with an amazing view. Holly was an exceptional host!"
Tinyhouse LakeView Cottage with a MILLION DOLLAR VIEW!! Kayaks available.
6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍
View from property
6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍
10.0 out of 10, Exceptional, (10)
"My group and I had a great time on our retreat to Kentucky. There was plenty of room for us to play games around the house and relax by the pool. We spent most of our time in the beautiful sun room. We were very impressed by the cleaniness of the house. Highly recommend!!!"
6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍
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The Little Hideaway at Beaver Creek (1 mile from Beaver Creek Marina)
Property grounds
The Little Hideaway at Beaver Creek (1 mile from Beaver Creek Marina)
10.0 out of 10, Exceptional, (32)
"Property was as advertised. It is a couple of minutes from Beaver Creek Marina and a couple minutes away from the general store. We had plenty of room for two guys. Our time was there devoted to fishing most of the time. Property had plenty of room for our truck and boat. Grill was not good, but we did grill on it. Nice fire pit with plenty of firewood. Porch was as big as the room inside. It rained a lot and we hung out on the porch when we were not on the lake. Owner and host were very...
The Little Hideaway at Beaver Creek (1 mile from Beaver Creek Marina)
Birdsong cabin
Property grounds
Birdsong cabin
10.0 out of 10, Exceptional, (8)
"The property was great. The cabin including the separate wash house was clean. Our dog loved the baby goats there. It was a great weekend"
Birdsong cabin
Private Catch And Release Lake--Boat Rental Included! Close to Lake Cumberland!
Exterior
Private Catch And Release Lake--Boat Rental Included! Close to Lake Cumberland!
10.0 out of 10, Exceptional, (217)
"Very well maintained grounds and the cabin was comfortable. Peace and quiet for the most part as can be expected on a farm. The hosts were attentive and provided everything you could ask for. As the title entails, 2 dozen duck were always around but, not a nuisance. Watching large catfish, bass, bluegill and turtles in the pond was nice."
Private Catch And Release Lake--Boat Rental Included! Close to Lake Cumberland!
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, (5)
"Property owner was very helpful, cabin was clean and had everything we needed. Great location!"
The price is NZ$727
per night
14 May - 15 May
Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!
3BR 3BA Cabin, with hot tub, 3 Pools, Boat Ramp with Dock 1 mile away.
Property grounds
3BR 3BA Cabin, with hot tub, 3 Pools, Boat Ramp with Dock 1 mile away.
10.0 out of 10, Exceptional, (50)
"We have stayed in several houses in this complex and this is the best. Well equipped and very user friendly."
3BR 3BA Cabin, with hot tub, 3 Pools, Boat Ramp with Dock 1 mile away.
Perfect Lake House on Lake Cumberland
Exterior
Perfect Lake House on Lake Cumberland
10.0 out of 10, Exceptional, (1)
"The home was exactly as pictured online. It was immaculately clean and owner was very responsive, even reaching out to us to simply make sure we were comfortable. There are areas to be together as a large group in the house and the layout also provides plenty of privacy with 8 separate bedrooms. We had an amazing stay and will definitely stay here again next year."
Perfect Lake House on Lake Cumberland
Cumberland River Cabin Rental
Private kitchen
Cumberland River Cabin Rental
10.0 out of 10, Exceptional, (245)
"We had an awesome vacation at the cabin. One of the most relaxing ones we have ever had. The cabin was excellent, with the plus of it being on the river we couldn't have asked for more!"
Cumberland River Cabin Rental
Lakeside Hideaway II - lakefront with hot tub / walk to boat ramp
Fridge, microwave, oven, stovetop
Lakeside Hideaway II - lakefront with hot tub / walk to boat ramp
10.0 out of 10, Exceptional, (27)
"This was a great place and they had anything you would ever need. One of the best places I have stayed. I loved that they communicated up front about an issue that was out of their hands. I would recommend this place to anyone. We had a great week with our family."
Lakeside Hideaway II - lakefront with hot tub / walk to boat ramp
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, (7)
"The house is beautiful, has everything you would need, easy process and the view is amazing. A great place for a relaxing weekend!"
NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking
⚓ Anchored on Lakeshore ⚓ 2 BR/2BA Lakeview Home <1/4 Mile to Public Boat Ramp
Property grounds
⚓ Anchored on Lakeshore ⚓ 2 BR/2BA Lakeview Home <1/4 Mile to Public Boat Ramp
10.0 out of 10, Exceptional, (8)
"Our family enjoyed being able to stay at a beautiful place while coming for a family funeral. We loved the views and the comfortable furniture and beds. We would definitely stay again."
⚓ Anchored on Lakeshore ⚓ 2 BR/2BA Lakeview Home <1/4 Mile to Public Boat Ramp
Relaxing Lakefront Getaway Near Marina, Park, & Town
Property grounds
Relaxing Lakefront Getaway Near Marina, Park, & Town
10.0 out of 10, Exceptional, (134)
"A favorite for us when we’re visiting my family in Nancy & Somerset! Great location cute home just like the photos and has everything you need!"
The price is NZ$416
per night
14 May - 15 May
Relaxing Lakefront Getaway Near Marina, Park, & Town
Large 8 Bedroom Home Overlooking Play Area, And Pool. Great For Family Reunions.
Fridge, microwave, oven, stovetop
Large 8 Bedroom Home Overlooking Play Area, And Pool. Great For Family Reunions.
9.8 out of 10, Exceptional, (54)
"There was nice amount of space for all seventeen of us at this clean two story duplex. We enjoyed the recreation area at the bottom of the hill. Visiting Mill Spring Mills Historical sight was fun for everyone. However, the highlight of our trip was getting to see the Moonbow at Cumberland Falls on the only clear night of our trip. This is a very nice place to stay, with plenty to do even on cold winter days."
Large 8 Bedroom Home Overlooking Play Area, And Pool. Great For Family Reunions.
Private Lake Cumberland Lodge with Breathtaking Views, Sleeps 20+
Interior
Private Lake Cumberland Lodge with Breathtaking Views, Sleeps 20+
9.8 out of 10, Exceptional, (7)
"The home is beautiful! Our kids and grandkids stayed at the home ages 0-61 there were 16 of us. We had an awesome time. The house was plenty big enough for everyone. The kitchen is well equipped. We enjoyed the hot tub also. Brett was very easy to work with and answered all my questions."
Private Lake Cumberland Lodge with Breathtaking Views, Sleeps 20+
Charming Get-A-Way 11C- Fun, Lake Cumberland, Golf Carts, Pickleball, Pool
Fridge, microwave, stovetop, dishwasher
Charming Get-A-Way 11C- Fun, Lake Cumberland, Golf Carts, Pickleball, Pool
9.8 out of 10, Exceptional, (30)
"The cabin was perfect! Great place to get away from everything and just relax."
Charming Get-A-Way 11C- Fun, Lake Cumberland, Golf Carts, Pickleball, Pool
Lake and Mountain Views
Terrace/patio
Lake and Mountain Views
9.8 out of 10, Exceptional, (47)
"Absolutely gorgeous cabin! Had everything we needed and was very clean and organized! We will definitely be back!"
Lake and Mountain Views
Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!
Terrace/patio
Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!
9.8 out of 10, Exceptional, (18)
"Great place to stay"
Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!
Cabin in the tree tops - Somerset, KY
Exterior
Cabin in the tree tops - Somerset, KY
9.8 out of 10, Exceptional, (6)
"The cabin was nice and cozy. We loved the simplicity of it all. The waffles and chips/salsa left for us were a great treat."
Cabin in the tree tops - Somerset, KY
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.

Other types of properties in Monticello you may be interested in

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, (86)
"The location was quiet and like the listing states."
Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!
Tinyhouse LakeView Cottage with a MILLION DOLLAR VIEW!! Kayaks available.
Property grounds
Tinyhouse LakeView Cottage with a MILLION DOLLAR VIEW!! Kayaks available.
10.0 out of 10, Exceptional, (31)
"The property was perfect with an amazing view. Holly was an exceptional host!"
Tinyhouse LakeView Cottage with a MILLION DOLLAR VIEW!! Kayaks available.
6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍
View from property
6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍
10.0 out of 10, Exceptional, (10)
"My group and I had a great time on our retreat to Kentucky. There was plenty of room for us to play games around the house and relax by the pool. We spent most of our time in the beautiful sun room. We were very impressed by the cleaniness of the house. Highly recommend!!!"
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.

Frequently asked questions

Can I find a holiday rental in Monticello?

Yes, there are holiday rentals close to the most popular sights in Monticello, or you can select a more secluded option if you're looking for a relaxing stay. Discover why Monticello is known for its marina and lakeside. Make sure you have time to check out the basketball games and wineries during your trip.

What are some of the best holiday rentals that Monticello has to offer?

Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!: This highly rated holiday home rental in Monticello is located on the waterfront, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub. Our travellers also rate 6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍 as a favourite home for rent in Monticello.

How many holiday rentals are there in Monticello?

With 48 Expedia holiday rentals, you're guaranteed to find just the right place for your Monticello stay.

What’s there to see and do in Monticello?

Daniel Boone National Forest and Cumberland River are a couple of scenic spots to enjoy the outdoors, whereas Wayne County Historical Museum is one of the cultural attractions. In the wider area, you’ll find Lake Cumberland Winery and Lake Cumberland State Resort Park.

What’s a holiday rental in Monticello like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Monticello. Holiday rentals feature extras like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy front desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for family trips.