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Top Holiday Rentals in Monticello

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!

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😍

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."
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.

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.

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.

9.6 out of 10, Exceptional, (226)
"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

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.

10.0 out of 10, Exceptional, (147)
"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.

9.8 out of 10, Exceptional, (8)
Cumberland Haven! One mile to Cumberland Point boat ramp and park.

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

10.0 out of 10, Exceptional, (18)
"Absolutely loved our short time in this home! Very clean and well furnished! We hope to stay again soon!"
The price is £298
includes taxes & fees
20 Aug - 21 Aug
Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!

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.

10.0 out of 10, Exceptional, (179)
"This is a phenomenal property to stay at. Plenty of space and comfortable.beds. I loved the pool table downstairs and we used the fire pit to make s'mores.Jamestown Marina is just a couple of minutes away which was great for us.We've already booked again in September."
The price is £281
includes taxes & fees
13 Aug - 14 Aug
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

10.0 out of 10, Exceptional, (3)
"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 £138
includes taxes & fees
18 Aug - 19 Aug
LAKE CUMBERLAND Get-a-Way! Charming House. BOAT RAMP NEARBY - Wifi - RV Hookups

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 £276
includes taxes & fees
20 Aug - 21 Aug
Private Cottage at Lake Cumberland Resort- a gated lakefront Community

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

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

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 £368
includes taxes & fees
18 Aug - 19 Aug
Charming 5-bedroom/3-bath home with easy access to Lake Cumberland

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!

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

Lakeside 3 bedroom chalet with hot tub!!

8.8 out of 10, Excellent, (6)
"Dale Hollow Lake is amazing. The cabins are very well cared for. The staff are also amazing. The only, singular complaint was that the WiFi is weak and spotty; it'll kick you off or not allow you on if there is too much traffic. "
Lakeside 3 bedroom chalet with hot tub!!
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 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 4 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 Lake Cumberland Luxury #2! Amazing Lake views, hot tub, fire pit! as a favourite home for rent in Monticello.

How many holiday rentals are there in Monticello?

With 43 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?

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 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.