A winding fence on a grassy hill with horses grazing.

Monticello Holiday Rentals

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Monticello holiday rentals

Living area

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 HK$600
HK$1,491 total
includes taxes & fees
1 Sept - 2 Sept
The Cozy Cabell Cottage
Property grounds

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 HK$1,355
HK$4,469 total
includes taxes & fees
1 Sept - 2 Sept
Lake Access ~ King Ensuites w/ fireplaces~ Hot Tub~ Fire Pit~ Boat Ramp
Private kitchen

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 HK$1,679
HK$2,119 total
includes taxes & fees
1 Sept - 2 Sept
Lakeside Escape - Charming home centrally located on Lake Cumberland
Interior

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 HK$324
HK$1,403 total
includes taxes & fees
1 Sept - 2 Sept
Timy Home near Wolf Creek Marina & multiple boat ramps with a full kitchen
Private kitchen

5. 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, (28 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 HK$635
HK$1,590 total
includes taxes & fees
3 Sept - 4 Sept
Newly renovated near Rowena, Grider and Wolf Creek Dam
Living area

6. 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 HK$980
HK$1,729 total
includes taxes & fees
1 Sept - 2 Sept
Lake Cumberland "Lake Daze Cabin" near Clearwater
Pool

7. 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 HK$628
HK$2,758 total
includes taxes & fees
1 Sept - 2 Sept
Private Cottage at Lake Cumberland Resort- a gated lakefront Community
Dining

8. 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 HK$706
HK$1,634 total
includes taxes & fees
1 Sept - 2 Sept
New Near Jamestown Dock - A
Room

9. 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 HK$699
HK$1,479 total
includes taxes & fees
1 Sept - 2 Sept
Studio Cottage on the Square, entire rental unit in Jamestown, Kentucky
Living area

10. 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 HK$804
HK$2,740 total
includes taxes & fees
1 Sept - 2 Sept
NEW HOT TUB Cozy Cabin Cumberland River near Lake Cumberland~Firepit~New build
Terrace/patio

11. 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 HK$882
HK$1,698 total
includes taxes & fees
1 Sept - 2 Sept
Cozy Cabin
Beach

12. 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 HK$1,176
HK$2,723 total
includes taxes & fees
9 Sept - 10 Sept
Wolf Creek Crossing Lake House Beach & Boat Launch .5 miles at Jabez Landing
Exterior

13. 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 HK$933
HK$1,521 total
includes taxes & fees
8 Sept - 9 Sept
CRISTY'S CABIN - cozy and quaint - where the deer and the ants play!
Room

14. 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, (7 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 HK$894
HK$2,213 total
includes taxes & fees
7 Sept - 8 Sept
LAKE CUMBERLAND Get-a-Way! Charming House. BOAT RAMP NEARBY - Wifi - RV Hookups
Exterior

15. Cordial chalet with a balcony to have coffee with the squirrels

Cordial chalet with a balcony to have coffee with the squirrels
Somerset
9.8 out of 10, Exceptional, (21 reviews)
"Beautiful house in a nice location. Very clean also"
United States
Julia
The price is HK$1,164
HK$1,465 total
includes taxes & fees
1 Sept - 2 Sept
Cordial chalet with a balcony to have coffee with the squirrels
Interior

16. 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 HK$1,019
HK$2,031 total
includes taxes & fees
7 Sept - 8 Sept
Avery Acres
Beach

17. Unique Hexagon Cottage Atop Marina · Boat Parking · 3 En Suite Baths · Pets okay

Unique Hexagon Cottage Atop Marina · Boat Parking · 3 En Suite Baths · Pets okay
Jamestown
10.0 out of 10, Exceptional, (214 reviews)
"We felt like we were at home! Very clean and comfortable home with everything we needed. Communication with the host was flawless. This was my families first trip to Lake Cumberland and it was everything we thought it would be. Beautiful lake! We will definitely be coming back and staying at the Hexagon cottage again."
United States
Joleen
The price is HK$1,058
HK$3,068 total
includes taxes & fees
1 Sept - 2 Sept
Unique Hexagon Cottage Atop Marina · Boat Parking · 3 En Suite Baths · Pets okay
Private kitchen

18. 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 HK$1,235
HK$3,038 total
includes taxes & fees
1 Sept - 2 Sept
Lake Cabin, Fishing Access, swimming, walk to lake, boat parking, fenced yard!
Outdoor dining

19. 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 HK$1,037
HK$2,241 total
includes taxes & fees
1 Sept - 2 Sept
Lake Cumberland Cabin
Terrace/patio

20. Charming 1-bedroom fish shack in Somerset with WiFi and AC

Charming 1-bedroom fish shack in Somerset with WiFi and AC
Somerset
9.8 out of 10, Exceptional, (17 reviews)
"Property was perfect for our needs, very close to restaurants and shops. Very well maintained Would absolutely stay again.."
United States
David W.
The price is HK$882
HK$1,145 total
includes taxes & fees
1 Sept - 2 Sept
Charming 1-bedroom fish shack in Somerset with WiFi and AC
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

Lake Bluff Paradise on Lake Cumberland. Game Room and seasonal Hot Tub!

Lake Bluff Paradise on Lake Cumberland. Game Room and seasonal Hot Tub!

10/10 Excellent
"We had a shot two night stay for my bachelor trip. It was awesome great view of the lake with a fun game room to keep us entertained."
Josh B. 2-night trip
Posted 12 hours ago
Lake Bluff Paradise on Lake Cumberland. Game Room and seasonal Hot Tub!

Find out more about Monticello

Search for holiday rentals in Monticello on Expedia! You can easily find your home rentals, villas, holiday apartments in Monticello using one of the methods below:

  • View our selection of featured holiday rentals in Monticello
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  • Enter your travel dates to view the best deals on holiday rentals in Monticello while they last

Look no further and take a look at our great range of rental properties in Monticello!

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

How many holiday rentals are there in Monticello?

With 45 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.