Book Holiday Homes in Monticello

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

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

Cozy 1-bedroom house in charming Allardt with AC, WiFi

Cozy 1-bedroom house in charming Allardt with AC, WiFi

Allardt TN
The price is AU$186 per night from 4 Jan to 5 Jan
AU$186
4 Jan - 5 Jan 2026
includes taxes & fees
This vacation home is 6 mi (9.7 km) from Allardt Town Hall and 6 mi (9.7 km) from Colditz Cove State Natural Area.
Opens in a new windowCozy 1-bedroom house in charming Allardt with AC, WiFi
Cumberland Lake House

Cumberland Lake House

Nancy KY
When you stay at this vacation home in Nancy, you'll be 7 minutes by car from Cumberland Point Recreation Area.
Opens in a new windowCumberland Lake House
6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more😍

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

Monticello KY
Located in Monticello, this vacation home is within a 15-minute drive of Cumberland River and Burnside Library.
Opens in a new window6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more😍
Save an average of 15% on thousands of hotels when you're signed in
Amazing 5BR House with Lake & Mountain Views in Gated Resort

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

Burnside KY
With a stay at this vacation home in Burnside, you'll be on a lake, and 9.7 mi (15.5 km) from Cumberland River and 9.9 mi (16 km) from Burnside Marina.
Opens in a new windowAmazing 5BR House with Lake & Mountain Views in Gated Resort
Lakeside Hideaway I - newly renovated lakefront with hot tub / walk to boat ramp

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

Burnside KY
With a stay at this vacation home in Burnside, you'll be on the waterfront, and 10.6 mi (17 km) from Cumberland River and 11.1 mi (17.9 km) from Burnside ...
Opens in a new windowLakeside Hideaway I - newly renovated lakefront with hot tub / walk to boat ramp
Remodeled House Near Jamestown Marina, Room to Park Your Boat in Driveway!

Remodeled House Near Jamestown Marina, Room to Park Your Boat in Driveway!

Jamestown KY
The price is AU$593 per night from 29 Dec to 30 Dec
AU$593
29 Dec - 30 Dec
includes taxes & fees
Located in Jamestown, this vacation home is a 5-minute drive from Jamestown Marina and 5 minutes from Cumberland River.
Opens in a new windowRemodeled House Near Jamestown Marina, Room to Park Your Boat in Driveway!
White Oak Cottage - Resort Pool, Boat Slip

White Oak Cottage - Resort Pool, Boat Slip

Burnside KY
The price is AU$582 per night from 27 Jan to 28 Jan
AU$582
27 Jan - 28 Jan 2026
includes taxes & fees
With a stay at this vacation home in Somerset, you'll be on a lake, a 5-minute walk from Cumberland River and a 3-minute drive from Burnside Library.
Opens in a new windowWhite Oak Cottage - Resort Pool, Boat Slip
Lake house. Less than 3 miles from beautiful Lake Cumberland.

Lake house. Less than 3 miles from beautiful Lake Cumberland.

Jamestown KY
The price is AU$372 per night from 29 Dec to 30 Dec
AU$372
29 Dec - 30 Dec
includes taxes & fees
When you stay at this vacation home in Jamestown, you'll be on a lake, within a 10-minute walk of Judicial Center Fountain Park and The Park at Jamestown ...
Opens in a new windowLake house. Less than 3 miles from beautiful Lake Cumberland.
LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.

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

Jamestown KY
The price is AU$910 per night from 2 Jan to 3 Jan
AU$910
2 Jan - 3 Jan 2026
includes taxes & fees
When you stay at this vacation home in Jamestown, you'll be on the waterfront, within a 5-minute drive of The Park at Jamestown Square and Judicial Center Fountain ...
Opens in a new windowLAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.
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
294 Holiday Homes
Lowest Price
AU$186
Highest Price
AU$910
Popular accommodation
Cozy 1-bedroom house in charming Allardt with AC, WiFi, Cumberland Lake House, 6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more😍, Amazing 5BR House with Lake & Mountain Views in Gated Resort, Lakeside Hideaway I - newly renovated lakefront with hot tub / walk to boat ramp, Remodeled House Near Jamestown Marina, Room to Park Your Boat in Driveway! , White Oak Cottage - Resort Pool, Boat Slip, Lake house. Less than 3 miles from beautiful Lake Cumberland., LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.

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
The price is AU$197 per night from 29 Dec to 30 Dec
AU$197
29 Dec - 30 Dec
includes taxes & fees
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.
Opens in a new windowBest Western Lake Cumberland Inn
Large 8 Bedroom Home Overlooking Play Area, And Pool. Great For Family Reunions.

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

Monticello KY
Located in Monticello, this vacation home is in a rural location, within a 15-minute walk of Lake Cumberland Winery and Conley Bottom Marina.
Opens in a new windowLarge 8 Bedroom Home Overlooking Play Area, And Pool. Great For Family Reunions.
6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more😍

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

Monticello KY
Located in Monticello, this vacation home is within a 15-minute drive of Cumberland River and Burnside Library.
Opens in a new window6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more😍
Save an average of 15% on thousands of hotels when you're signed in
4 Bedrooms, Heated Private pool, hot tub, Game room, and Water Front View!

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

Monticello KY
Located in Monticello, this vacation home is on a lake, within a 15-minute drive of Cumberland River and Burnside Library.
Opens in a new window4 Bedrooms, Heated Private pool, hot tub, Game room, and Water Front View!
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.