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Monticello Vacation Rentals

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Check prices for these dates

Tonight
Jun 23 - Jun 24
Tomorrow
Jun 24 - Jun 25
This weekend
Jun 27 - Jun 29
Next weekend
Jul 4 - Jul 6

Vacation Rentals in Monticello

Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!
Outdoor spa tub

Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!

10.0 out of 10, Exceptional, (109)
"Pleasant quiet area to stay"
Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!
6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more😍
Interior

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

9.8 out of 10, Exceptional, (22)
"We had a great time at this spacious, well equipped house with lake view. Great location to marina."
The price is ￥109,568
￥174,454 total
includes taxes & fees
Jul 22 - Jul 23
6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more😍
Lake Cumberland Luxury #2! Amazing Lake views, hot tub, fire pit!
Terrace/patio

Lake Cumberland Luxury #2! Amazing Lake views, hot tub, fire pit!

10.0 out of 10, Exceptional, (4)
"Excellent bang for your buck! Truly a wonderful stay and great for the price! I will DEFINITELY be trying to come back again! Stay with confidence! "
Lake Cumberland Luxury #2! Amazing Lake views, hot tub, fire pit!
This charming cozy cottage has a private hot tub, deck for fishing.
Property grounds

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

9.8 out of 10, Exceptional, (149)
"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.
Charming Getaway At Conley Bottom Resort/Lake Cumberland
Smart TV, video games, DVD player

Charming Getaway At Conley Bottom Resort/Lake Cumberland

Charming Getaway At Conley Bottom Resort/Lake Cumberland
The Little Hideaway at Beaver Creek (1 mile from Beaver Creek Marina)
Outdoor dining

The Little Hideaway at Beaver Creek (1 mile from Beaver Creek Marina)

9.8 out of 10, Exceptional, (40)
"My wife and I enjoyed our two night stay at The Little Hideaway. The hosts were top notch and the cabin had everything that we needed for our getaway."
The Little Hideaway at Beaver Creek (1 mile from Beaver Creek Marina)
LAKE CUMBERLAND, FENCED YARD, FIRE PIT, HOT TUB, 100 meg internet, FIREPLACE
Outdoor spa tub

LAKE CUMBERLAND, FENCED YARD, FIRE PIT, HOT TUB, 100 meg internet, FIREPLACE

10.0 out of 10, Exceptional, (244)
"Just a nice quiet weekend. Beautiful property. One of the best hosts I have ever worked with. Kris was great the whole time with anything we needed. "
LAKE CUMBERLAND, FENCED YARD, FIRE PIT, HOT TUB, 100 meg internet, FIREPLACE
Private Cottage at Lake Cumberland Resort- a gated lakefront Community
Outdoor pool

Private Cottage at Lake Cumberland Resort- a gated lakefront Community

9.4 out of 10, Exceptional, (122)
"We had an awsome time, very secluded and private, Calvin was awsome, we didn't get in until late in the evening..he stayed awake to make sure we made it safe...the cabin has everything you need for a relaxing getaway in the mountains. "
The price is ￥9,204
￥48,315 total
includes taxes & fees
Jun 25 - Jun 26
Private Cottage at Lake Cumberland Resort- a gated lakefront Community
Lake View Loft Cabin is only 2 miles from Wolf Creek Marina, Lake Cumberland KY
Smart TV, video games, DVD player, books

Lake View Loft Cabin is only 2 miles from Wolf Creek Marina, Lake Cumberland KY

2.0 star property
9.0 out of 10, Wonderful, (2)
"This cabin was adorable ! Very clean and nice. We didn’t do much there due to spending time with family at another cabin. However , I loved the view and it did have a nice porch to sit on and the upstairs is super cute. Will definitely be coming back if we are ever up that way. "
Lake View Loft Cabin is only 2 miles from Wolf Creek Marina, Lake Cumberland KY
Big South Fork! Peaceful, Relaxing, On the Trails…Six Decks ~ Nature’s Paradise!
Exterior

Big South Fork! Peaceful, Relaxing, On the Trails…Six Decks ~ Nature’s Paradise!

9.8 out of 10, Exceptional, (58)
"Lovely location that felt like home. Enjoyed our stay and would love to stay again. "
Big South Fork! Peaceful, Relaxing, On the Trails…Six Decks ~ Nature’s Paradise!
NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking
Interior

NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking

10.0 out of 10, Exceptional, (39)
"Beautiful views of the lake, clean and comfortable beds. Overall perfect quiet retreat for me. Will be back again!"
NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking
Pet friendly suite that overlooks Lake Cumberland's Safe Harbor Jamestown #107
Interior

Pet friendly suite that overlooks Lake Cumberland's Safe Harbor Jamestown #107

2.0 star property
8.0 out of 10, Very Good, (2)
"This was a very quiet relaxing spot. The view from the hotel room is gorgeous. The patio overlooking Lake Cumberland was so relaxing. Rent a boat or bring one it is a boaters dream come true. The office staff was great very friendly. House keeping was great. I would highly recommend this location. The areas around was great. All the parks and nature areas. The views are breath taking. We were only three hours away from home. A vacation we truly needed . "
Pet friendly suite that overlooks Lake Cumberland's Safe Harbor Jamestown #107
Cumberland River Cabin Rental
Fridge, microwave, oven, stovetop

Cumberland River Cabin Rental

10.0 out of 10, Exceptional, (294)
"Great place"
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, (39)
"We had a great time and the accommodations were great Thank you Tracy"
Lakeside Hideaway II - lakefront with hot tub / walk to boat ramp
Little blue house on the lake
Interior

Little blue house on the lake

9.0 out of 10, Wonderful, (18)
"A great weekend in a nice house. Exceeded expectations."
Little blue house on the lake
3BR 3BA Cabin, with hot tub, 3 Pools, Boat Ramp with Dock 1 mile away.
Interior

3BR 3BA Cabin, with hot tub, 3 Pools, Boat Ramp with Dock 1 mile away.

10.0 out of 10, Exceptional, (61)
"It’s a beautiful property. Spent the weekend for my birthday/Valentines day. The host was great and responsive. Beautiful scenery."
3BR 3BA Cabin, with hot tub, 3 Pools, Boat Ramp with Dock 1 mile away.
LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY
Outdoor dining

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

10.0 out of 10, Exceptional, (140)
"Beautiful home w beautiful views.Home was graciously stocked from toilet paper, to Kleenex,dish soap and dishwasher detergent."
The price is ￥63,257
￥123,848 total
includes taxes & fees
Jul 24 - Jul 25
LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY
Rustic Luxury Lakefront Cabin in Beautiful Wooded Surroundings
Property grounds

Rustic Luxury Lakefront Cabin in Beautiful Wooded Surroundings

9.6 out of 10, Exceptional, (174)
"Great location! Beautiful inside and out. Very homey."
Rustic Luxury Lakefront Cabin in Beautiful Wooded Surroundings
JAMESTOWN Marina, LCKY. boat parking. pool table. 3 full baths. pet friendly.
Property grounds

JAMESTOWN Marina, LCKY. boat parking. pool table. 3 full baths. pet friendly.

10.0 out of 10, Exceptional, (172)
"It was nice subtle place."
The price is ￥28,926
￥62,166 total
includes taxes & fees
Jul 6 - Jul 7
JAMESTOWN Marina, LCKY. boat parking. pool table. 3 full baths. pet friendly.
Lake Days & Starry Nights – Your Perfect Getaway Awaits
Indoor spa tub

Lake Days & Starry Nights – Your Perfect Getaway Awaits

9.8 out of 10, Exceptional, (181)
"This was a great place to stay. "
The price is ￥22,206
￥51,053 total
includes taxes & fees
Jul 10 - Jul 11
Lake Days & Starry Nights – Your Perfect Getaway Awaits
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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Frequently asked questions

Can I find a vacation rental in Monticello?

Yes, we offer vacation rentals close to top points of interest in Monticello, or you can choose a 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 vacation rentals that Monticello has to offer?

Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!: Visitors like this Monticello vacation home rental. It is located on the waterfront and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub. Our travelers also rate 6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more😍 as a favorite home for rent in Monticello.

How many vacation rentals are there in Monticello?

With 45 Expedia vacation rentals, you're sure to find just the right place for your Monticello stay.

What’s there to see and do in Monticello?

Cumberland River and Mill Springs Mill Park are a couple of scenic spots to enjoy the outdoors, whereas Wayne County Historical Museum is one of the cultural attractions. While here, Lake Cumberland Winery and Conley Bottom Marina are other places worth a visit.

What’s a vacation rental in Monticello like?

A vacation rental is a private property you can book for several days or longer in Monticello. Vacation rentals offer amenities like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a clean environment, a vacation rental can offer a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for small groups.