A winding fence on a grassy hill with horses grazing.

Holiday Rentals in Monticello

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Monticello holiday rentals

A cozy living room with a sofa, coffee table, and a painting on the wall.

1. The Cozy Cabell Cottage

The Cozy Cabell Cottage
Monticello
9.8 out of 10, Exceptional, (56 reviews)
"Great clean place to stay with good parking. It was very quiet and felt safe as well. Would stay again. The host did an excellent job with making sure the place felt comfortable and convenient."
United States
tim w.
The price is €167
includes taxes & fees
1 Sept - 2 Sept
The Cozy Cabell Cottage

2. Lake Access ~ King Ensuites w/ fireplaces~ Hot Tub~ Fire Pit~ Boat Ramp

Lake Access ~ King Ensuites w/ fireplaces~ Hot Tub~ Fire Pit~ Boat Ramp
Monticello
10.0 out of 10, Exceptional, (39 reviews)
"Had such an amazing time in this beautiful home. Will definitely be back!"
United States
Monika H.
The price is €484
includes taxes & fees
2 Sept - 3 Sept
Lake Access ~ King Ensuites w/ fireplaces~ Hot Tub~ Fire Pit~ Boat Ramp
A modern kitchen with wooden cabinets, stainless steel appliances, and a central island with bar stools.

3. Lakeside Escape - Charming home centrally located on Lake Cumberland

Lakeside Escape - Charming home centrally located on Lake Cumberland
Monticello
10.0 out of 10, Exceptional, (1 review)
"Clean house, pet friendly and our teens loved the game room"
United States
michelle d.
The price is €226
includes taxes & fees
23 Aug - 24 Aug
Lakeside Escape - Charming home centrally located on Lake Cumberland
A kitchen with a stainless steel refrigerator, a coffee maker, and a trash bin.

4. Timy Home near Wolf Creek Marina & multiple boat ramps with a full kitchen

Timy Home near Wolf Creek Marina & multiple boat ramps with a full kitchen
Nancy
9.4 out of 10, Exceptional, (41 reviews)
"Great place for cheap!"
United States
Jamie M.
The price is €160
includes taxes & fees
31 Aug - 1 Sept
Timy Home near Wolf Creek Marina & multiple boat ramps with a full kitchen
A modern kitchen with wooden cabinets, a dining table, and a bench. There is a living area with a sofa and a coffee table.

5. Lake Cumberland "Lake Daze Cabin" near Clearwater

Lake Cumberland "Lake Daze Cabin" near Clearwater
Nancy
9.0 out of 10, Wonderful, (6 reviews)
"Place was great for just our weekend boating. Nice parking area. Little challenging to find just because building hidden by the storage facility. Also pull out couch was messed up so sleeking 5 worked but 6 wouldn’t have."
United States
Trevor
The price is €190
includes taxes & fees
2 Sept - 3 Sept
Lake Cumberland "Lake Daze Cabin" near Clearwater
A cozy room with a floral sofa, a TV, and a sign that reads "Everglow Hollow".

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

LAKE CUMBERLAND Get-a-Way! Charming House. BOAT RAMP NEARBY - Wifi - RV Hookups
Faubush
9.8 out of 10, Exceptional, (6 reviews)
"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. "
Canada
Morgan P.
The price is €229
includes taxes & fees
24 Aug - 25 Aug
LAKE CUMBERLAND Get-a-Way! Charming House. BOAT RAMP NEARBY - Wifi - RV Hookups
A wooden cabin with a porch, a star emblem, and a 'No Shoes Nation' sign.

7. Cozy Cabin

Cozy Cabin
Burnside
9.2 out of 10, Wonderful, (14 reviews)
"It was an amazing stay very clean close to the river very relaxing"
United States
Jeremy C.
The price is €187
includes taxes & fees
21 Aug - 22 Aug
Cozy Cabin
A cozy cabin interior with a wooden staircase, a living area with a sofa and coffee table, a kitchen with white cabinets and appliances, and a welcome sign on the wall.

8. NEW HOT TUB Cozy Cabin Cumberland River near Lake Cumberland~Firepit~New build

NEW HOT TUB Cozy Cabin Cumberland River near Lake Cumberland~Firepit~New build
Jamestown
9.2 out of 10, Wonderful, (19 reviews)
"Such a lovely property. Very cozy and inviting. We will definitely stay again."
United States
Jennifer S.
The price is €273
includes taxes & fees
21 Aug - 22 Aug
NEW HOT TUB Cozy Cabin Cumberland River near Lake Cumberland~Firepit~New build
A modern kitchen with white cabinets, a dining table with chairs, and a living area with a sofa and a TV.

9. New Near Jamestown Dock - A

New Near Jamestown Dock - A
Jamestown
9.6 out of 10, Exceptional, (27 reviews)
"The place was perfect for what we needed. It's right next to Pepe's and Giovanni's, two of my favorite Cumberland restaurants. It was also just 22 minutes from State Park Marina. You can hear everything from every room; we all went to bed and woke up at the same time, so it didn't bother us. I also loved the AC units in each room."
United States
Jennifer
The price is €182
includes taxes & fees
23 Aug - 24 Aug
New Near Jamestown Dock - A
A compact kitchen with a black stove, white cabinets, a refrigerator, and a coffee maker.

10. Newly renovated near Rowena, Grider and Wolf Creek Dam

Newly renovated near Rowena, Grider and Wolf Creek Dam
Albany
9.6 out of 10, Exceptional, (26 reviews)
"Great place to stay, property is very well maintained. Ample parking for truck and boat, highly recommend, will stay here again. "
United States
Trent N.
The price is €179
includes taxes & fees
24 Aug - 25 Aug
Newly renovated near Rowena, Grider and Wolf Creek Dam

11. CRISTY'S CABIN - cozy and quaint - where the deer and the ants play!

CRISTY'S CABIN - cozy and quaint - where the deer and the ants play!
Burnside
9.6 out of 10, Exceptional, (10 reviews)
"The place is okay the cabin is nice but is dirty"
United States
Mohamed
The price is €174
includes taxes & fees
15 Sept - 16 Sept
CRISTY'S CABIN - cozy and quaint - where the deer and the ants play!
A modern kitchen with dark cabinets, a central island with stools, stainless steel appliances, and pendant lighting.

12. Lake Cabin, Fishing Access, swimming, walk to lake, boat parking, fenced yard!

Lake Cabin, Fishing Access, swimming, walk to lake, boat parking, fenced yard!
Nancy
10.0 out of 10, Exceptional, (6 reviews)
"We loved our stay while at Cumberland. This is a great place to stay just as described. We will definitely book again. "
United States
Tricia H.
The price is €341
includes taxes & fees
2 Sept - 3 Sept
Lake Cabin, Fishing Access, swimming, walk to lake, boat parking, fenced yard!
A covered outdoor deck with a table and chairs, surrounded by a wooden railing, overlooking a grassy area with trees.

13. Lake Cumberland Cabin

Lake Cumberland Cabin
Bronston
9.8 out of 10, Exceptional, (17 reviews)
"No complaints for this stay"
United States
Trisha E.
The price is €248
includes taxes & fees
31 Aug - 1 Sept
Lake Cumberland Cabin
A hot tub with a view of a forested area.

14. Cozy 2-Bedroom Cabin Overlooking Beautiful Lake Cumberland

Cozy 2-Bedroom Cabin Overlooking Beautiful Lake Cumberland
Nancy
9.6 out of 10, Exceptional, (4 reviews)
"Very nice place "
United States
kashyap p.
The price is €222
includes taxes & fees
20 Sept - 21 Sept
Cozy 2-Bedroom Cabin Overlooking Beautiful Lake Cumberland
A wooden cabin interior with a dining area, sofa, fireplace, and a TV mounted on the wall.

15. Hot Tub~Firepit~Riverfront~Near Lake Cumberland

Hot Tub~Firepit~Riverfront~Near Lake Cumberland
Jamestown
10.0 out of 10, Exceptional, (3 reviews)
"Very clean and quiet. The beds were comfortable and the house was stocked with nice touches like laundry pods and coffee. I would definitely stay there again!"
United States
Christine V.
The price is €278
includes taxes & fees
23 Aug - 24 Aug
Hot Tub~Firepit~Riverfront~Near Lake Cumberland
A calm lake with a pebbly shore and dense forest in the background.

16. Wolf Creek Crossing Lake House Beach & Boat Launch .5 miles at Jabez Landing

Wolf Creek Crossing Lake House Beach & Boat Launch .5 miles at Jabez Landing
Nancy
10.0 out of 10, Exceptional, (7 reviews)
"Host was wonderful and the place was fantastic!"
United States
Oliver C.
The price is €273
includes taxes & fees
2 Sept - 3 Sept
Wolf Creek Crossing Lake House Beach & Boat Launch .5 miles at Jabez Landing
A bedroom with a bed, nightstands, a TV, and a wall-mounted shelf.

17. Studio Cottage on the Square, entire rental unit in Jamestown, Kentucky

Studio Cottage on the Square, entire rental unit in Jamestown, Kentucky
Jamestown
8.8 out of 10, Excellent, (13 reviews)
"Great location."
United States
Donald S.
The price is €223
includes taxes & fees
31 Aug - 1 Sept
Studio Cottage on the Square, entire rental unit in Jamestown, Kentucky
A wooden deck with a railing, a ceiling fan, and a view of trees in the background.

18. Calming 1-bedroom yellow door house close to lake with Wi-Fi, AC

Calming 1-bedroom yellow door house close to lake with Wi-Fi, AC
Somerset
10.0 out of 10, Exceptional, (17 reviews)
"10/10 Great place. Definitely would stay here again."
United States
Pascal C.
The price is €158
includes taxes & fees
1 Sept - 2 Sept
Calming 1-bedroom yellow door house close to lake with Wi-Fi, AC
A wooden interior with a wooden door, a wreath, a small table, and a vase of flowers.

19. Avery Acres

Avery Acres
Albany
9.4 out of 10, Exceptional, (6 reviews)
"The host was awesome - excellent communication and customer service. The house was extremely clean, well equipped, and roomy. The bed was comfortable. We had everything that we needed! We will definitely stay at Avery Acres again. Recommend it!"
United States
Kandy F.
The price is €199
includes taxes & fees
1 Sept - 2 Sept
Avery Acres
A rectangular swimming pool with a tiled deck.

20. Private Cottage at Lake Cumberland Resort- a gated lakefront Community

Private Cottage at Lake Cumberland Resort- a gated lakefront Community
Burnside
9.4 out of 10, Exceptional, (135 reviews)
"Nice and quiet, house super clean. Like being at home away from home."
United States
Paul R.
The price is €335
includes taxes & fees
14 Sept - 15 Sept
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.
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Top Monticello Hotel Reviews

Cumberland Falls State Resort Park

Cumberland Falls State Resort Park

10/10 Excellent
"I wish I'd had time to stay for more than one night. I was on my way through, driving from North Carolina to Illinois, and this was a good stopping point. I avoid chain hotels as much as possible and looked in advance for a place near Cumberland Falls. You can't get any closer than this! There was plenty of time to go check out the falls during my brief stay before getting back on the road. The Caribou coffee that was on offer in the room was delicious, so I didn't even feel the need to go search for coffee on my way out. Otherwise, the room had all the basics that I needed aside from paper towels in the kitchenette. If I had one complaint, it would be that the door adjoining mine and the next unit could stand to be soundproofed. I heard every sound the kids in the next unit were making. Fortunately they went to bed at a decent time and didn't keep me awake all night, so it was all good. But I would recommend this as an improvement that could be made to the property."
Amanda 1-night trip
Posted 20 hours ago
Cumberland Falls State Resort Park

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, apart-hotels, 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 €174 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 Sunshine Escape: Spacious 6BR Home w/ Outdoor Oasis & Fire Pit, Near Marina and Large 8 Bedroom Home Overlooking Play Area, And Pool. Great For Family Reunions..

How many holiday rentals are there in Monticello?

With 47 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 Mill Springs Mill Park are a couple of scenic spots to enjoy the outdoors, whereas Wayne County Historical Museum is one of the cultural attractions. While here, Conley Bottom Marina and Lake Cumberland Winery 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.