Book Holiday Homes in Monticello

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Featured Holiday Homes in Monticello

Dale Hollow Retreat: Boat Parking-Fire Pit

Dale Hollow Retreat: Boat Parking-Fire Pit

Burkesville KY
Located in Burkesville, this vacation home is a 5-minute drive from Dale Hollow Lake State Park and 6 minutes from Dale Hollow Lake State Resort Park Golf ...
Opens in a new windowDale Hollow Retreat: Boat Parking-Fire Pit
Lake Days & Starry Nights – Your Perfect Getaway Awaits

Lake Days & Starry Nights – Your Perfect Getaway Awaits

Burnside KY
With a stay at this vacation home in Burnside, you'll be on a lake, and 9.1 mi (14.7 km) from Cumberland River and 9.7 mi (15.6 km) from Burnside Marina.
Opens in a new windowLake Days & Starry Nights – Your Perfect Getaway Awaits
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$949 per night from 18 May to 19 May
AU$949
18 May - 19 May
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 Jamestown City ...
Opens in a new windowLAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.
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"Eagle's Cliff" at Lake Cumberland. Relaxing Beautiful Front Porch Lake View!

"Eagle's Cliff" at Lake Cumberland. Relaxing Beautiful Front Porch Lake View!

Nancy KY
With a stay at this vacation home in Nancy, you'll be within a 15-minute drive of Zollicoffer Park and Mill Springs National Battlefield Visitor Center.
Opens in a new window"Eagle's Cliff" at Lake Cumberland. Relaxing Beautiful Front Porch Lake View!
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!
Lakeside Hideaway II - lakefront with hot tub / walk to boat ramp

Lakeside Hideaway II - 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 10.5 mi (17 km) from Cumberland River and 11.1 mi (17.9 km) from Burnside ...
Opens in a new windowLakeside Hideaway II - lakefront with hot tub / walk to boat ramp
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
“Red’s House” located in Oneida city limits

“Red’s House” located in Oneida city limits

Oneida TN
With a stay at this vacation home in Oneida, you'll be within a 5-minute drive of Big South Fork Medical Center and Oneida City Park.
Opens in a new window“Red’s House” located in Oneida city limits
Lake Bluff Paradise on Lake Cumberland. Game room and seasonal hot tub!

Lake Bluff Paradise on Lake Cumberland. Game room and seasonal hot tub!

Monticello KY
Located in Monticello, this vacation home is on the waterfront, within a 15-minute drive of Cumberland River and Burnside Library.
Opens in a new windowLake Bluff Paradise on Lake Cumberland. Game room and seasonal hot tub!
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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
357 Holiday Homes
Lowest Price
AU$182
Highest Price
AU$949
Popular accommodation
Dale Hollow Retreat: Boat Parking-Fire Pit, Lake Days & Starry Nights – Your Perfect Getaway Awaits, LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY., "Eagle's Cliff" at Lake Cumberland. Relaxing Beautiful Front Porch Lake View! , 4 Bedrooms, Heated Private pool, hot tub, Game room, and Water Front View!, Lakeside Hideaway II - lakefront with hot tub / walk to boat ramp, Cumberland Lake House, “Red’s House” located in Oneida city limits, Lake Bluff Paradise on Lake Cumberland. Game room and seasonal hot tub!

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$182 per night from 14 May to 15 May
AU$182
14 May - 15 May
includes taxes & fees
Located in Monticello, Best Western Lake Cumberland Inn is a 4-minute drive from Wayne County Historical Museum and 8 minutes from Cumberland River.
Opens in a new windowBest 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 KY
When you stay at this cottage in Monticello, you'll be on the waterfront, within a 15-minute walk of Lake Cumberland Winery and Conley Bottom Marina.
Opens in a new windowThis charming cozy cottage has a private hot tub, deck for fishing.
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.