Photo by Lisa Klein

Monticello Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Holiday Rentals in Monticello

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

9.8 out of 10, Exceptional, (30)
"We only stayed a short time but really enjoyed the pool and hot tub. The lake view and fire pit were a hit as well! "
6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more😍

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

9.8 out of 10, Exceptional, (154)
"Great place. Very quite and peaceful. "
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, (102)
"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, (121)
"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, (63)
"Relaxing! PoolWasAwesome"
Large 8 Bedroom Home Overlooking Play Area, And Pool. Great For Family Reunions.

Cozy Cabin - Lake Cumberland - Hot Tub

9.6 out of 10, Exceptional, (30)
"The cabin was wonderful. We had a wonderful experience and will rent the cabin again. The atmosphere was great. Wonderful weather and we just adored the cabin."
Cozy Cabin - Lake Cumberland - Hot Tub

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

10.0 out of 10, Exceptional, (184)
"Great location and close to the marina. We thoroughly enjoyed our stay and the great communication with the host! "
The price is AU$513
includes taxes & fees
7 Oct - 8 Oct
Above J’town Marina, LCKY. boat parking. 3 full baths. pool table. pet friendly.

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

9.6 out of 10, Exceptional, (232)
"Loved everything about our stay. The cabin was awesome, the hosts are fantastic and we plan to come back. "
Lake Front Home with community boat ramp. Private, close to marinas and town.

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

10.0 out of 10, Exceptional, (150)
"The house is beautiful, clean, and perfect for large groups. Suzanne was great to work with and very professional. Highly recommend her property and this beautiful home!"
The price is AU$929
includes taxes & fees
7 Oct - 8 Oct
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
9.8 out of 10, Exceptional, (7)
"The property was great for a group trip and we enjoyed the amenities provided."
The price is AU$625
includes taxes & fees
13 Oct - 14 Oct
Cozy Lakehouse – Game Room, Pet-Friendly, Near Boatramp, 3-Season room!

Little blue house on the lake

9.2 out of 10, Wonderful, (24)
"Loved our stay! Beautiful place. Just wish the lake access was better but due to the rain it was hard to make it down the steep hill. "
Little blue house on the lake

Birdsong cabin

9.2 out of 10, Wonderful, (31)
"Lovely spot to stay. If you're wanting to get away from the hustle and bustle, this definitely the place you want to go to relax."
Birdsong cabin

2 Bedroom lakeside to Dale Hollow Lake!

9.0 out of 10, Wonderful, (8)
"We have been going to Dale Hollow for over 30 years and we fall in love with it more evwrytime we go "
2 Bedroom lakeside to Dale Hollow Lake!

Welcome to Charming Get-A-Way – Your Ultimate Escape!

9.8 out of 10, Exceptional, (36)
"Great location and cabin. "
Welcome to Charming Get-A-Way – Your Ultimate Escape!

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

10.0 out of 10, Exceptional, (24)
"Perfect location to the Jamestown ramp. Wi-Fi did not work the whole time If you are a grown adult and plan to sleep on the bunk beds just don’t haha. Two bedrooms were cozy and place is perfect for a weekend get away. Thanks Hot tub is very nice "
The price is AU$599
includes taxes & fees
12 Oct - 13 Oct
Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!

Lakin’ It Easy at Lake Cumberland Resort Burnside KY 4 KING BEDS & 4 FULL BATHS

10.0 out of 10, Exceptional, (100)
"Nice and clean and big enough for few families "
Lakin’ It Easy at Lake Cumberland Resort Burnside KY 4 KING BEDS & 4 FULL BATHS

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

Lakeside 3 bedroom chalet with hot tub!!

9.0 out of 10, Wonderful, (7)
"Nice"
Lakeside 3 bedroom chalet with hot tub!!

Cordial chalet with a balcony to have coffee with the squirrels

2.0 star property
9.8 out of 10, Exceptional, (15)
"Nice quiet neighborhood close to many amenities. Easy access to highways and river system."
The price is AU$267
includes taxes & fees
13 Oct - 14 Oct
Cordial chalet with a balcony to have coffee with the squirrels

Private Cottage at Lake Cumberland Resort- a gated lakefront Community

9.4 out of 10, Exceptional, (130)
"It was great we had nice time the cabin was fine but definitely need some tender loving care "
The price is AU$537
includes taxes & fees
8 Oct - 9 Oct
Private Cottage at Lake Cumberland Resort- a gated lakefront Community
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.
Save an average of 15% on thousands of hotels when you're signed in

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$267 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.