Book Holiday Homes in Monticello

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Featured Holiday Homes in Monticello

Cozy Gray House

Cozy Gray House

Oneida
The price is AU$289 per night from 1 Dec to 2 Dec
AU$289
includes taxes & fees
1 Dec - 2 Dec
Located in Oneida, this vacation home is on a river, within a 10-minute drive of Big South Fork Medical Center and Oneida City Park.
Cozy Gray House
Centrally located house at Pond Meadow Place

Centrally located house at Pond Meadow Place

Somerset
A stay at this vacation home places you in the heart of Somerset, within a 5-minute drive of Somerset Community College and The Center For Rural ...
Centrally located house at Pond Meadow Place
Lake Retreat at Lake Cumberland Resort

Lake Retreat at Lake Cumberland Resort

Burnside
When you stay at this vacation home in Burnside, you'll be on a lake and steps from Daniel Boone National Forest.
Lake Retreat at Lake Cumberland Resort
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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!😍
Pool / Grill,  Dale Hollow Lake and nearby Sunset Marina with Mountain view

Pool / Grill, Dale Hollow Lake and nearby Sunset Marina with Mountain view

Byrdstown
Located in Byrdstown, this vacation home is on a lake, within a 5-minute drive of Dale Hollow Reservoir and Cordell Hull.
Pool / Grill, Dale Hollow Lake and nearby Sunset Marina with Mountain view
Located on the picturesque shores of Lake Cumberland.

Located on the picturesque shores of Lake Cumberland.

Jamestown
When you stay at this vacation home in Jamestown, you'll be 14 minutes by car from Lake Cumberland State Resort Park.
Located on the picturesque shores of Lake Cumberland.
3 miles from Wolf Creek Dam! Boat and camper parking available

3 miles from Wolf Creek Dam! Boat and camper parking available

Highway
Located in Albany, this vacation home is within a 15-minute drive of Wolf Creek National Fish Hatchery and Lake Cumberland State Resort Park.
3 miles from Wolf Creek Dam! Boat and camper parking available
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
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
When you stay at this vacation home in Burnside, you'll be on the waterfront and steps from Daniel Boone National Forest.
Lakeside Hideaway I - newly renovated lakefront with hot tub / walk to boat ramp
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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
260 Holiday Homes
Lowest Price
AU$178
Highest Price
AU$289
Popular accommodation
Cozy Gray House, Centrally located house at Pond Meadow Place, Lake Retreat at Lake Cumberland Resort, 6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍 , Pool / Grill, Dale Hollow Lake and nearby Sunset Marina with Mountain view, Located on the picturesque shores of Lake Cumberland. , 3 miles from Wolf Creek Dam! Boat and camper parking available, LOG Cabin, 5 miles from town, but very country setting, Lakeside Hideaway I - newly renovated lakefront with hot tub / walk to boat ramp

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$178 per night from 26 Nov to 27 Nov
AU$178
includes taxes & fees
26 Nov - 27 Nov
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.

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^Subject to availability and chosen travel dates.