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Monticello Holiday Rentals

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Holiday Rentals in Monticello

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

9.8 out of 10, Exceptional, (28)
"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😍

Cozy Cabin - Lake Cumberland - Hot Tub

9.6 out of 10, Exceptional, (28)
"The peace and quiet and seclusion can’t be overstated. Remote, but perfect for a couple or a small family wanting to get away!"
Cozy Cabin - Lake Cumberland - Hot Tub

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

9.8 out of 10, Exceptional, (152)
"Description and photos were spot on correct . It was very clean and our contact Steve was friendly and helpful . "
This charming cozy cottage has a private hot tub, deck for fishing.

4 Bedrooms, Heated Private pool, hot tub, Game room, and Water Front View!

9.6 out of 10, Exceptional, (101)
"Great house and lost of fun things to do!"
4 Bedrooms, Heated Private pool, hot tub, Game room, and Water Front View!

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

10.0 out of 10, Exceptional, (118)
"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!

Large 8 Bedroom Home Overlooking Play Area, And Pool. Great For Family Reunions.

9.8 out of 10, Exceptional, (61)
"was quiet and relaxing. would be nice to have a walkin shower and grab bars"
Large 8 Bedroom Home Overlooking Play Area, And Pool. Great For Family Reunions.

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!

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

9.6 out of 10, Exceptional, (231)
"The view was amazing, the location was only 5 miles from town with a pretty country drive, the home was clean, cozy, and charming! "
Lake Front Home with community boat ramp. Private, close to marinas and town.

Lakefront Cabin: Private Water Access, Boat Parking, Lake View & Wi-Fi

9.8 out of 10, Exceptional, (225)
"Beautiful property, lots and lots of stairs though. Gorgeous views"
Lakefront Cabin: Private Water Access, Boat Parking, Lake View & Wi-Fi

Cumberland River Cabin Rental

10.0 out of 10, Exceptional, (308)
"Super spot. Well outfitted kitchen. "
Cumberland River Cabin Rental

Lake Cumberland custom log cabin home on 32 wooded acres

10.0 out of 10, Exceptional, (191)
"It was very beautiful and relaxing. Everything was so comfortable and inviting. "
Lake Cumberland custom log cabin home on 32 wooded acres

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!! "
The price is AU$961
includes taxes & fees
15 Sept - 16 Sept
LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.

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

10.0 out of 10, Exceptional, (50)
"Great location and as advertised. "
NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking

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

2.0 star property
9.8 out of 10, Exceptional, (7)
"Our stay was great, with a lot of little details taken care of that you don't normally expect. Like condiments already in the fridge, laundry detergent in the laundry room, etc. The house and property were very clean and the view of the lake was awesome. Tucked away in a very quiet area. Jordan checked in with us on Saturday morning and was easy to reach as needed. My wife loved cooking on the Blackstone. Would definitely book again."
The price is AU$625
includes taxes & fees
15 Sept - 16 Sept
Cozy Lakehouse – Game Room, Pet-Friendly, Near Boatramp, 3-Season room!

Private Catch And Release Lake--Boat Rental Included! Close to Lake Cumberland!

10.0 out of 10, Exceptional, (236)
"This was the perfect weekend getaway for me and my husband. We enjoyed fishing, feeding the ducks and just shutting the world off for 2 days. Its exactly what we were hoping for and can't wait for our next trip. "
Private Catch And Release Lake--Boat Rental Included! Close to Lake Cumberland!

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, (8)
"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

Charming cabin retreat: cozy, scenic, and perfect for a relaxing getaway!

9.6 out of 10, Exceptional, (19)
"great house for 2 couples. loved the outdoor spaces and quiet neighborhood."
The price is AU$478
includes taxes & fees
7 Oct - 8 Oct
Charming cabin retreat: cozy, scenic, and perfect for a relaxing getaway!

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

10.0 out of 10, Exceptional, (11)
"House has a great layout and right on the lake owners were awesome to work with "
The price is AU$644
includes taxes & fees
21 Sept - 22 Sept
Joy On The Lake · Cumberland Canvas: Lake View, Fire Pit & Game Room

Boating Mecca: Near Dale Hollow Lake & Golf!

10.0 out of 10, Exceptional, (79)
"Everything was top notch. We will definitely stay here again for future trips. "
The price is AU$266
includes taxes & fees
21 Sept - 22 Sept
Boating Mecca: Near Dale Hollow Lake & Golf!

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

10.0 out of 10, Exceptional, (12)
"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
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

Find out more about Monticello

Find out more about Monticello

Everything you need to know about Monticello holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Monticello holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Monticello holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Monticello holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Monticello. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Monticello holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Monticello holiday rentals we have selected for you start as low as AU$266 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Monticello rentals

At Expedia, we put the best Monticello holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Monticello rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Monticello holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Monticello. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more😍: This highly rated holiday home rental in Monticello offers an outdoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. Other favourite homes for rent in Monticello are 4 Bedrooms, Heated Private pool, hot tub, Game room, and Water Front View! and Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!.

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.