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Monticello Vacation Rentals

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Vacation Rentals in Monticello

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

10.0 out of 10, Exceptional, (113)
"Very well appointed cabin. Great location and view. Host were very responsive, which is sign of a great host. We will definitely be renting here again on our next trip"
Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!

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

9.8 out of 10, Exceptional, (73)
"Everything was so good, the place was amazing and the area was beautiful. We are ready to go again!! Thanks for sharing your place with us!,"
Lake house with boat ramp access across the street & tons of boat parking space.

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

9.8 out of 10, Exceptional, (151)
"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.

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

10.0 out of 10, Exceptional, (5)
"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!

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

9.8 out of 10, Exceptional, (23)
"We had a great time at this spacious, well equipped house with lake view. Great location to marina."
The price is CA $755
CA $1,294 total
includes taxes & fees
Aug 13 - Aug 14
6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more😍

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

2.0 star property
9.4 out of 10, Exceptional, (3)
"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

Lake Days & Starry Nights – Your Perfect Getaway Awaits

9.6 out of 10, Exceptional, (184)
"This was a great place to stay. "
Lake Days & Starry Nights – Your Perfect Getaway Awaits

Spacious Cabin on Dale Hollow Lake w/ Hot Tub!

9.4 out of 10, Exceptional, (55)
"My large family enjoyed the stay at the “Cliffhanger” house. Beautiful view and had everything we needed."
Spacious Cabin on Dale Hollow Lake w/ Hot Tub!

Lake Front Home with community boat ramp. Private, close to marinas and town.

9.6 out of 10, Exceptional, (224)
"Nice and cozy. We enjoyed the beautiful view. Very clean and had everything you need to unplug and relax. "
Lake Front Home with community boat ramp. Private, close to marinas and town.

Private Cottage at Lake Cumberland Resort- a gated lakefront Community

9.4 out of 10, Exceptional, (127)
"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 CA $100
CA $470 total
includes taxes & fees
Jul 23 - Jul 24
Private Cottage at Lake Cumberland Resort- a gated lakefront Community

Charming 5-bedroom/3-bath home with easy access to Lake Cumberland

10.0 out of 10, Exceptional, (1)
"Jenn was super responsive and gave us plenty of info on fishing/boating access in the area. The house was a great size with a cute unique layout. Huge deck for plenty of outside hang time and close to a boat ramp to easily drop my canoe in. Just a few minutes from the State Park too! "
The price is CA $362
CA $628 total
includes taxes & fees
Jul 28 - Jul 29
Charming 5-bedroom/3-bath home with easy access to Lake Cumberland

Peaceful Whitley City Cabin on 10 Wooded Acres!

9.4 out of 10, Exceptional, (19)
"Great property with everything you need to relax and unplug."
Peaceful Whitley City Cabin on 10 Wooded Acres!

Birdsong cabin

9.2 out of 10, Wonderful, (29)
"This was a great cabin, very clean and had everything we needed. Enjoyed swimming and fishing in the nearby river. The host Amber was very helpful and a great communicator. We would definitely stay here again. "
Birdsong cabin

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

10.0 out of 10, Exceptional, (144)
"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.

Cozy Lakehouse – Game Room, Pet-Friendly, Near Boatramp, 3-Season room!

2.0 star property
10.0 out of 10, Exceptional, (4)
"The property was great for a group trip and we enjoyed the amenities provided."
The price is CA $216
CA $530 total
includes taxes & fees
Jul 30 - Jul 31
Cozy Lakehouse – Game Room, Pet-Friendly, Near Boatramp, 3-Season room!

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

10.0 out of 10, Exceptional, (46)
"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

Lake Cumberland Hideaway Cabin-2 miles above Jtown Marina-Boat Parking+Fire Pit!

9.8 out of 10, Exceptional, (65)
"The property surrounding this cabin is lovely and the cabin itself was clean and comfortable. We would definitely recommend it for a family vacation."
Lake Cumberland Hideaway Cabin-2 miles above Jtown Marina-Boat Parking+Fire Pit!

Cabin in the woods

9.4 out of 10, Exceptional, (18)
"Easy to disconnect from the world. About as good as a cabin in the woods can be yet close enough to civilization. Plenty of hiking trails nearby that are not overtrodden. "
Cabin in the woods

Woodsend Bend 3 BR Condo, with Pool, AC, WiFi, Golf Course, Restaurant

Woodsend Bend 3 BR Condo, with Pool, AC, WiFi, Golf Course, Restaurant

The Holiday Hutt at Dale Hollow Lake-Close to Sunset, Bball Court, Movie Theater

10.0 out of 10, Exceptional, (11)
"The home was amazing. Considering returning next summer with a few families. "
The price is CA $2,059
CA $3,453 total
includes taxes & fees
Aug 6 - Aug 7
The Holiday Hutt at Dale Hollow Lake-Close to Sunset, Bball Court, Movie Theater
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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Top Monticello Hotel Reviews

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!: This Monticello vacation home rental 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.

How many vacation rentals are there in Monticello?

With 44 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 Fall Creek Recreation Area 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.