Photo by Lisa Klein

Monticello Vacation Rentals

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Vacation Rentals in Monticello

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!
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)
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.
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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!😍
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+
Property grounds
LOG Cabin, 5 miles from town, but very country setting
9.6 out of 10, Exceptional, (71)
"We really enjoyed our stay this past weekend. We hauled a vehicle for the cruise in and had plenty of room for the truck and trailer. Our ONLY negative was that the carpet was a bit worn in places, but the place was so clean and comfortable. Thanks for a great stay!"
LOG Cabin, 5 miles from town, but very country setting
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
Dining
Lake Front Home with community boat ramp. Private, close to marinas and town.
9.6 out of 10, Exceptional, (198)
"My husband & I stayed at this beautiful house for a week for our anniversary and it was absolutely wonderful! The view was beautiful and the house was spotless. Comfy furniture to relax after our days of sightseeing. The ride to the house was all paved and easy to maneuver, especially for us Floridians! Linda is awesome and communicated excellently. We went to Cumberland Falls (amazing!) and also the Cave Hill Winery among many other historical sites. Most were less than 30 min away. Lots to do...
Lake Front Home with community boat ramp. Private, close to marinas and town.
Exterior
Private Catch And Release Lake--Boat Rental Included! Close to Lake Cumberland!
10.0 out of 10, Exceptional, (217)
"Our cabin on the lake was wonderful! A terrific getaway that we plan to return too!"
Private Catch And Release Lake--Boat Rental Included! Close to Lake Cumberland!
View from property
NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking
10.0 out of 10, Exceptional, (8)
"Wonderful, relaxing, place to stay. Enjoyed every minute. Highly recommend"
NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking
Property grounds
Cozy Cabin Located in gated resort near Lake Cumberland. Pool & boat ramp onsite
9.4 out of 10, Exceptional, (138)
"the cabin was very clean and provided us with what we needed for the trip"
Cozy Cabin Located in gated resort near Lake Cumberland. Pool & boat ramp onsite
Property grounds
Rustic Luxury Lakefront Cabin in Beautiful Wooded Surroundings
9.6 out of 10, Exceptional, (162)
"My family stayed for a long weekend and enjoyed the comfortable setup of this very clean home. The description matches the website and the cabin decor is adorable. The owners stocked the cabin well. We had a partial lake view even with the trees!"
Rustic Luxury Lakefront Cabin in Beautiful Wooded Surroundings
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 CA $219
CA $532 total
includes taxes & fees
Jun 17 - Jun 18
Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!
Private kitchen
Cumberland River Cabin Rental
10.0 out of 10, Exceptional, (248)
"We came to fish. Everyone was comfortable. Great access to the river."
Cumberland River Cabin Rental
Private kitchen
Lake Cumberland Hideaway Cabin-2 miles above Jtown Marina-Boat Parking+Fire Pit!
9.8 out of 10, Exceptional, (55)
"The driveway and the house was really nice ! Had enough room to turn your boat around . The area was very quiet and relaxing . The home was decorated nicely . The walk way going in the back of the house did have some loose boards on path . We enjoyed our stay . Wish there were more restaurants in the area of the town but we made do . Our next trip back will be when the marina is in season though . Cause when we were there everything was closed , but we did enjoy putting our fishing boat in the...
Lake Cumberland Hideaway Cabin-2 miles above Jtown Marina-Boat Parking+Fire Pit!
Outdoor pool
Private Cottage at Lake Cumberland Resort- a gated lakefront Community
9.4 out of 10, Exceptional, (113)
"We had a wonderful time at the cabin. The area is scenic, the hot tub was amazing, it was hot and running upon our arrival. The check in and check out process was easygoing."
Private Cottage at Lake Cumberland Resort- a gated lakefront Community
Property grounds
Birdsong cabin
9.6 out of 10, Exceptional, (9)
"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
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
Property grounds
Lake Retreat at Lake Cumberland Resort
9.8 out of 10, Exceptional, (152)
"excellent place great hosts"
Lake Retreat at Lake Cumberland Resort
Smart TV
LAKE FRONT CABIN with Large Deck.
10.0 out of 10, Exceptional, (18)
"The rental was amazing. Felt like home. Beautiful site"
LAKE FRONT CABIN with Large Deck.
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.

Monticello Vacation Rental Travel Info

Number of vacation rentals
16
Popular accommodation
Monticello private vacation homes
Known landmarks
Wayne County Historical Museum and Lake Cumberland Winery
International airports
Nashville, TN (BNA-Nashville Intl.) and Louisville, KY (SDF-Louisville Intl.)

Other types of properties in Monticello you may be interested in

Indoor pool
Best Western Lake Cumberland Inn
2.5 star property
9.0 out of 10, Wonderful, (261)
"Good location priced right"
The price is CA $164
CA $180 total
includes taxes & fees
Jun 3 - Jun 4
Best Western Lake Cumberland Inn
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!
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.
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Monticello. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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 3 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 spa tub. Our travelers also rate 6 Bedroom home, 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 48 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?

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 larger area, you’ll find Lake Cumberland Winery and Lake Cumberland State Resort Park.

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.

Recent reviews of Monticello properties
Expedia verified reviews

Cumberland Falls State Resort Park

Cumberland Falls State Resort Park

5/5 Excellent
"Staff was considerate. We really enjoyed our stay and will probably come back for another getaway from the hustle and bustle."
A verified traveller stayed at Cumberland Falls State Resort Park
Posted 3 days ago
Cumberland Falls State Resort Park