Book Holiday Homes in Monticello

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Monticello

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

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

Science Hill
Located in Somerset, this vacation home is in a rural location, within a 15-minute drive of SomerSplash and The Center For Rural Development.
LOG Cabin, 5 miles from town, but very country setting
Luxe Lake Barndo w/ 2 King Suites! Hot Tub, Fire Pit, 1/8 mile to boat ramp!

Luxe Lake Barndo w/ 2 King Suites! Hot Tub, Fire Pit, 1/8 mile to boat ramp!

Monticello
The price is AU$584 per night from 7 Jan to 8 Jan
AU$584
includes taxes & fees
7 Jan - 8 Jan 2025
When you stay at this vacation home in Monticello, you'll be on a lake and within a 5-minute drive of Cumberland River.
Luxe Lake Barndo w/ 2 King Suites! Hot Tub, Fire Pit, 1/8 mile to boat ramp!
6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍

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

Monticello
Located in Monticello, this vacation home is within a 15-minute drive of Cumberland River and Burnside Marina.
6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍
Save an average of 15% on thousands of hotels when you're signed in
Little blue house on the lake

Little blue house on the lake

Nancy
When you stay at this vacation home in Nancy, you'll be on a lake and 9 minutes by foot from Cumberland River.
Little blue house on the lake
"Shore Thing", Cozy Lake Cumberland Cabin - Hot Tub, Fire Pit, Minutes from Lake

"Shore Thing", Cozy Lake Cumberland Cabin - Hot Tub, Fire Pit, Minutes from Lake

Nancy
With a stay at this vacation home in Nancy, you'll be on a lake, and 16.1 mi (26 km) from Mill Springs National Battlefield Visitor Center and 16.8 mi (27 km) ...
"Shore Thing", Cozy Lake Cumberland Cabin - Hot Tub, Fire Pit, Minutes from Lake
Near Cumberland River, 12 miles from Wolf Creek Dam, in Creelsboro community

Near Cumberland River, 12 miles from Wolf Creek Dam, in Creelsboro community

Jamestown
With a stay at this vacation home in Jamestown, you'll be 8.5 mi (13.6 km) from Lake Cumberland State Resort Park and 12 mi (19.3 km) from Wolf Creek National ...
Near Cumberland River, 12 miles from Wolf Creek Dam, in Creelsboro community
Lake Cumberland Ohana.  Kid friendly, best views, hot tub.

Lake Cumberland Ohana. Kid friendly, best views, hot tub.

Burnside
When you stay at this vacation home in Burnside, you'll be on a lake and steps from Daniel Boone National Forest.
Lake Cumberland Ohana. Kid friendly, best views, hot tub.
Captivating 2-bedroom, garage door house with WiFi, AC in welcoming Somerset

Captivating 2-bedroom, garage door house with WiFi, AC in welcoming Somerset

2 out of 5
Somerset
The price is AU$259 per night from 9 Jan to 10 Jan
AU$259
includes taxes & fees
9 Jan - 10 Jan 2025
Located in Somerset, this vacation home is within a 10-minute drive of SomerSplash and Somerset Community College.
Captivating 2-bedroom, garage door house with WiFi, AC in welcoming Somerset
Charming 1-bedroom fish shack in Somerset with WiFi and AC

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

2 out of 5
Somerset
The price is AU$242 per night from 9 Jan to 10 Jan
AU$242
includes taxes & fees
9 Jan - 10 Jan 2025
With a stay at this vacation home in Somerset, you'll be within a 10-minute drive of SomerSplash and Somerset Community College.
Charming 1-bedroom fish shack in Somerset with WiFi and AC
Don't see what you're looking for?
See all available properties in Monticello
View all properties
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.

Monticello Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Monticello vacation homes are the perfect way for you to wing it.

Holiday houses in Monticello let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Monticello in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Monticello adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Monticello with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Monticello vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Monticello Holiday Homes essential information

Accommodation
256 Holiday Homes
Lowest Price
AU$186
Highest Price
AU$584
Popular accommodation
LOG Cabin, 5 miles from town, but very country setting, Luxe Lake Barndo w/ 2 King Suites! Hot Tub, Fire Pit, 1/8 mile to boat ramp!, 6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍 , Little blue house on the lake, "Shore Thing", Cozy Lake Cumberland Cabin - Hot Tub, Fire Pit, Minutes from Lake, Near Cumberland River, 12 miles from Wolf Creek Dam, in Creelsboro community, Lake Cumberland Ohana. Kid friendly, best views, hot tub., Captivating 2-bedroom, garage door house with WiFi, AC in welcoming Somerset , Charming 1-bedroom fish shack in Somerset with WiFi and AC

Top trending hotels in Monticello

Best Western Lake Cumberland Inn

Best Western Lake Cumberland Inn

2.5 out of 5
2030 E Highway 90, Monticello, KY
Fully refundableReserve now, pay when you stay
The price is AU$186 per night from 29 Dec to 30 Dec
AU$186
includes taxes & fees
29 Dec - 30 Dec
Located in Monticello, Best Western Lake Cumberland Inn is a 4-minute drive from Wayne County Historical Museum and 6 minutes from Wayne County Hospital.
Best Western Lake Cumberland Inn
This charming  cozy cottage has a private hot tub, deck for fishing.

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

monticello
Located in Monticello, this cottage is on the waterfront, a 1-minute drive from Lake Cumberland Winery and 8 minutes from Cumberland River.
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!

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

Monticello
Located in Monticello, this vacation home is on the waterfront, within a 15-minute drive of Cumberland River and Burnside Marina.
Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!
Save an average of 15% on thousands of hotels when you're signed in
6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍

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

Monticello
Located in Monticello, this vacation home is within a 15-minute drive of Cumberland River and Burnside Marina.
6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍
Don't see what you're looking for?
See all available properties in Monticello
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.