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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😍

Monticello
9.8 out of 10, Exceptional, (32)
"Perfect accommodation for our family group ages 2 to 85. Wonderful and relaxing week. Thank you!"
United States
Nancy L.
6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more😍

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

Monticello
9.6 out of 10, Exceptional, (106)
"We enjoyed our stay at the property. The pool and hot tub were wonderful!"
United States
Jenny M.
4 Bedrooms, Heated Private pool, hot tub, Game room, and Water Front View!

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

Monticello
9.8 out of 10, Exceptional, (63)
"Great spot close to lake cumberland and conley botom marina"
United States
Michael W.
Large 8 Bedroom Home Overlooking Play Area, And Pool. Great For Family Reunions.

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

monticello
9.8 out of 10, Exceptional, (160)
"We would like to stay there again because of all the amenities the manager was very friendly"
United States
Phil H.
This charming cozy cottage has a private hot tub, deck for fishing.

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

Monticello
10.0 out of 10, Exceptional, (124)
"Great place! Comfortable. Wonderful couple days."
United States
Colleen L.
Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!

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

Jamestown
10.0 out of 10, Exceptional, (154)
"Check in was very easy, beautiful home,views were pretty,overall great family time!"
United States
paige m.
The price is NZ$931
includes taxes & fees
16 Nov - 17 Nov
LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.

Lakeside 3 bedroom chalet with hot tub!!

Byrdstown
9.0 out of 10, Wonderful, (8)
"We had the best time. Cabin was very nice. Everything was close for the kids. We would definitely go back. The only downfall was the mattresses. They were horrible and caved in the middle. None of us got a good nights rest. And nobody could connect to wifi, even with the password it would continue to spin and never connect. Other than that, we enjoyed our stay very much "
United States
Tammy M.
Lakeside 3 bedroom chalet with hot tub!!

Private Cottage at Lake Cumberland Resort- a gated lakefront Community

Burnside
9.4 out of 10, Exceptional, (131)
"Took a little road trip to KY for our family vacation this year. They place is amazing. So spacious, very clean, communication with owner was great. I would say we will definitely rebook! "
United States
Amanda T.
The price is NZ$709
includes taxes & fees
16 Nov - 17 Nov
Private Cottage at Lake Cumberland Resort- a gated lakefront Community

LOG Cabin, 5 miles from town, but very country setting

Science Hill
9.6 out of 10, Exceptional, (96)
"Loved it!"
United States
Christy H.
LOG Cabin, 5 miles from town, but very country setting

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

Somerset
9.6 out of 10, Exceptional, (236)
"Loved everything about our stay. The cabin was awesome, the hosts are fantastic and we plan to come back. "
United States
Kim W.
Lake Front Home with community boat ramp. Private, close to marinas and town.

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

Jamestown
10.0 out of 10, Exceptional, (192)
"Overall we had a nice stay here. The extra driveway made it easy to park our boat which was a big reason for picking this property. The road is a bit narrow, so go slow. "
United States
Ben M.
The price is NZ$569
includes taxes & fees
23 Nov - 24 Nov
Above J’town Marina, LCKY. boat parking. 3 full baths. pool table. pet friendly.

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

Bronston
9.2 out of 10, Wonderful, (94)
"House was very clean with plenty of space. Convenient location to marinas."
United States
Joe O.
Lake View Home, Fire Pit, Grill, Fireplace, 5 minutes to boat ramp

Lakeside Hideaway I - newly renovated lakefront with hot tub / walk to boat ramp

Burnside
9.8 out of 10, Exceptional, (49)
"The property was updated and had everything you needed, very beautiful "
United States
Leonardo
Lakeside Hideaway I - newly renovated lakefront with hot tub / walk to boat ramp

Lakeside 3 Bedroom Chalet with a hot tub!

Byrdstown
9.0 out of 10, Wonderful, (6)
"Amazing stay, very nice hosts. Would stay again!!"
United States
Nicholas
Lakeside 3 Bedroom Chalet with a hot tub!

Rustic Luxury Lakefront Cabin in Beautiful Wooded Surroundings

Nancy
9.6 out of 10, Exceptional, (183)
"We loved our stay at this property! Nice location, quiet, relaxing, pretty views, everything there that we needed, and great memories made. Definitely recommend this rental!"
United States
Kara K.
Rustic Luxury Lakefront Cabin in Beautiful Wooded Surroundings

Lake View Loft Cabin is only 2 miles from Wolf Creek Marina, Lake Cumberland KY

2.0 star property
Nancy
9.0 out of 10, Wonderful, (12)
"All good as advertised"
United States
Paul E.
Lake View Loft Cabin is only 2 miles from Wolf Creek Marina, Lake Cumberland KY

Perfect Lake House on Lake Cumberland

Somerset
10.0 out of 10, Exceptional, (11)
"This house was the perfect place for our weekend! All of our children and grandchildren were there to celebrate my husband's birthday! I can't even begin to put into words how perfect this place was. There were 17 of us and nobody got in anybody else's way! All the bedrooms have different names, which was fun. The air hockey and pool table were in constant use, as well as cards and board games at the tables. The kitchen is very well furnished with any kind of spoon, ladle, or gadget you...
United States
Katy S.
Perfect Lake House on Lake Cumberland

2 Bedroom lakeside to Dale Hollow Lake!

Byrdstown
9.0 out of 10, Wonderful, (8)
"The cabins are right on the water perfect for fishing and boating. Our cabin was very nice and clean but our neighbors were complaining they did not have the same experience. Would definitely stay here again! "
United States
Brooke F.
2 Bedroom lakeside to Dale Hollow Lake!

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

Burnside
9.8 out of 10, Exceptional, (226)
"Excellent property! My family and friends enjoyed the amenities inside and outside the house. The boat dock was perfect for our pontoon, water trampoline and relaxing. The boat ramp was conveniently located close to the property. The kitchen was well equipped. The host was very responsive."
United States
Lometa S.
Lakefront Cabin: Private Water Access, Boat Parking, Lake View & Wi-Fi

Amazing 5BR House with Lake & Mountain Views in Gated Resort

Burnside
10.0 out of 10, Exceptional, (97)
"Even though we had no electricity after the first night, we made the best out of it and ended up managing to have a great time!! Our host (owner) was awesome!!! Gwen kept us updated all weekend after the tornado had come through! And was great!!"
United States
Lynn J.
Amazing 5BR House with Lake & Mountain Views in Gated Resort
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

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 favorite 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 depends 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 NZ$569 per night. Entering your travel dates in the search wizard you might find 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 Large 8 Bedroom Home Overlooking Play Area, And Pool. Great For Family Reunions. and 4 Bedrooms, Heated Private pool, hot tub, Game room, and Water Front View!.

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.