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Monticello Vacation Rentals

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Check prices for these dates

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Aug 9 - Aug 10
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Aug 10 - Aug 11
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Aug 15 - Aug 17
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Aug 22 - Aug 24

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, (116)
"First impression was wow. Very clean, beautiful location and a great game room. Very accommodation owners."
Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!
Lake Cumberland Luxury #2! Amazing Lake views, hot tub, fire pit!
Terrace/patio

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

9.8 out of 10, Exceptional, (8)
"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😍
Interior

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

9.8 out of 10, Exceptional, (25)
"We had a great time at this spacious, well equipped house with lake view. Great location to marina."
The price is ￥66,123
￥120,356 total
includes taxes & fees
Aug 13 - Aug 14
6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more😍
Lake house with boat ramp access across the street & tons of boat parking space.
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (74)
"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.
Property grounds

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

9.8 out of 10, Exceptional, (151)
"This was our anniversary, the place was well maintained and the manager was nice and accommodating "
This charming cozy cottage has a private hot tub, deck for fishing.
Lake Front Home with community boat ramp. Private, close to marinas and town.
Interior

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

9.6 out of 10, Exceptional, (225)
"It rained a lot, but we still had a great time. The property was just as advertised with an amazing view!"
Lake Front Home with community boat ramp. Private, close to marinas and town.
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
9.6 out of 10, Exceptional, (5)
"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 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, (146)
"Great Experience on the property and on the Lake!! "
LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.
Cumberland Haven! One mile to Cumberland Point boat ramp and park.
Terrace/patio

Cumberland Haven! One mile to Cumberland Point boat ramp and park.

10.0 out of 10, Exceptional, (7)
Cumberland Haven! One mile to Cumberland Point boat ramp and park.
Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!
Marina

Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!

10.0 out of 10, Exceptional, (17)
"Absolutely loved our short time in this home! Very clean and well furnished! We hope to stay again soon!"
The price is ￥23,510
￥57,505 total
includes taxes & fees
Aug 12 - Aug 13
Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!
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, (47)
"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
Above J’town Marina, LCKY. boat parking. 3 full baths. pool table. pet friendly.
Property grounds

Above J’town Marina, LCKY. boat parking. 3 full baths. pool table. pet friendly.

10.0 out of 10, Exceptional, (178)
"Enjoyed our time relaxing and spending time together away from responsibilities. Quiet and comfy. "
The price is ￥13,225
￥42,603 total
includes taxes & fees
Aug 11 - Aug 12
Above J’town Marina, LCKY. boat parking. 3 full baths. pool table. pet friendly.
LAKE CUMBERLAND Get-a-Way! Charming House. BOAT RAMP NEARBY - Wifi - RV Hookups
Exterior

LAKE CUMBERLAND Get-a-Way! Charming House. BOAT RAMP NEARBY - Wifi - RV Hookups

10.0 out of 10, Exceptional, (2)
"Everglow Hollow was great! We stayed for a long weekend and it was the perfect place to relax, while not being too far away from Lake Cumberland. Host also responded to questions right away and were very helpful. "
The price is ￥10,447
￥26,743 total
includes taxes & fees
Aug 11 - Aug 12
LAKE CUMBERLAND Get-a-Way! Charming House. BOAT RAMP NEARBY - Wifi - RV Hookups
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, (128)
"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 ￥13,078
￥53,294 total
includes taxes & fees
Aug 18 - Aug 19
Private Cottage at Lake Cumberland Resort- a gated lakefront Community
Lake View Home, Fire Pit, Grill, Fireplace, 5 minutes to boat ramp
Miscellaneous

Lake View Home, Fire Pit, Grill, Fireplace, 5 minutes to boat ramp

9.2 out of 10, Wonderful, (93)
"Had a great stay"
Lake View Home, Fire Pit, Grill, Fireplace, 5 minutes to boat ramp
The Holiday Hutt at Dale Hollow Lake-Close to Sunset, Bball Court, Movie Theater
Terrace/patio

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 Holiday Hutt at Dale Hollow Lake-Close to Sunset, Bball Court, Movie Theater
Charming 5-bedroom/3-bath home with easy access to Lake Cumberland
Fridge, microwave, oven, stovetop

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 ￥37,762
￥75,507 total
includes taxes & fees
Aug 18 - Aug 19
Charming 5-bedroom/3-bath home with easy access to Lake Cumberland
Spacious Cabin on Dale Hollow Lake w/ Hot Tub!
Interior

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!
BRAND NEW 3 Bedroom Modern Barndominium at Lake Cumberland .5 mi to boat launch!
Fridge, microwave, oven, stovetop

BRAND NEW 3 Bedroom Modern Barndominium at Lake Cumberland .5 mi to boat launch!

10.0 out of 10, Exceptional, (3)
"Property is nice. "
BRAND NEW 3 Bedroom Modern Barndominium at Lake Cumberland .5 mi to boat launch!
Joy On The Lake · Cumberland Canvas: Lake View, Fire Pit & Game Room
Fridge, microwave, oven, stovetop

Joy On The Lake · Cumberland Canvas: Lake View, Fire Pit & Game Room

10.0 out of 10, Exceptional, (11)
"It was a wonderful stay. Beautiful view!"
Joy On The Lake · Cumberland Canvas: Lake View, Fire Pit & Game Room
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

Lake Cumberland State Resort Park

Lake Cumberland State Resort Park

10/10 Excellent
"Dated but very pleasant especially sitting while watching deer and the lake. Food is unavailable weekdays at lodge but available for lunch and dinner at the dock, and good. Alcohol is better skipped at their bar. "
Richard 2-night trip
Posted 2 days ago
Lake Cumberland State Resort Park

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 Lake Cumberland Luxury #2! Amazing Lake views, hot tub, fire pit! as a favorite home for rent in Monticello.

How many vacation rentals are there in Monticello?

With 43 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.