Book Holiday Homes in Monticello

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Featured Holiday Homes in Monticello

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
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 ...
LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.
Cumberland Haven! One mile to Cumberland Point boat ramp and park.

Cumberland Haven! One mile to Cumberland Point boat ramp and park.

Nancy
With a stay at this vacation home in Nancy, you'll be steps from Cumberland River and a 2-minute drive from Cumberland Point Recreation Area.
Cumberland Haven! One mile to Cumberland Point boat ramp and park.
Historic Union Chapel Elementary School near Cumberland River & Lake

Historic Union Chapel Elementary School near Cumberland River & Lake

Jamestown
The price is AU$206 per night from 14 Aug to 15 Aug
AU$206
14 Aug - 15 Aug
includes taxes & fees
Located in Jamestown, this vacation home is on a lake, within a 15-minute drive of Cumberland River and Lake Cumberland State Resort Park.
Historic Union Chapel Elementary School near Cumberland River & Lake
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Conner Room Lakeside Inn at Dale Hollow - newly renovated near Dale Hollow Lake!

Conner Room Lakeside Inn at Dale Hollow - newly renovated near Dale Hollow Lake!

Monroe
Located in Byrdstown, this aparthotel is on a lake, a 2-minute drive from Dale Hollow Reservoir and 8 minutes from Cordell Hull Birthplace State Park.
Conner Room Lakeside Inn at Dale Hollow - newly renovated near Dale Hollow Lake!
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
The price is AU$282 per night from 25 Aug to 26 Aug
AU$282
25 Aug - 26 Aug
includes taxes & fees
With a stay at this vacation home in Nancy, you'll be 8.4 mi (13.6 km) from Wolf Creek Marina and 11.2 mi (18.1 km) from Mill Springs National Battlefield Visitor ...
LAKE CUMBERLAND Get-a-Way! Charming House. BOAT RAMP NEARBY - Wifi - RV Hookups
Cumberland Lake House

Cumberland Lake House

Nancy
When you stay at this vacation home in Nancy, you'll be 7 minutes by car from Cumberland Point Recreation Area.
Cumberland Lake House
Near Lake Cumberland: Monticello Home w/ Gazebo!

Near Lake Cumberland: Monticello Home w/ Gazebo!

Monticello
With a stay at this vacation home in Monticello, you'll be within a 5-minute drive of Mill Springs Mill Park and Cumberland River.
Near Lake Cumberland: Monticello Home w/ Gazebo!
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 Library.
Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!
NEW! Lake Fun: 6BR + Hot Tub + Game Room

NEW! Lake Fun: 6BR + Hot Tub + Game Room

Somerset
When you stay at this vacation home in Somerset, you'll be on a lake, within a 5-minute drive of Cumberland River and Burnside Library.
NEW! Lake Fun: 6BR + Hot Tub + Game Room
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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
336 Holiday Homes
Lowest Price
AU$206
Highest Price
AU$282
Popular accommodation
LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY., Cumberland Haven! One mile to Cumberland Point boat ramp and park., Historic Union Chapel Elementary School near Cumberland River & Lake, Conner Room Lakeside Inn at Dale Hollow - newly renovated near Dale Hollow Lake!, LAKE CUMBERLAND Get-a-Way! Charming House. BOAT RAMP NEARBY - Wifi - RV Hookups, Cumberland Lake House, Near Lake Cumberland: Monticello Home w/ Gazebo!, Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!, NEW! Lake Fun: 6BR + Hot Tub + Game Room

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$211 per night from 1 Sept to 2 Sept
AU$211
1 Sept - 2 Sept
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.
Best Western Lake Cumberland Inn
Lake Cumberland Luxury #2! Amazing Lake views, hot tub, fire pit!

Lake Cumberland Luxury #2! Amazing Lake views, hot tub, fire pit!

Monticello
Located in Monticello, this vacation home is on the waterfront, within a 15-minute drive of Burnside Library and Cole Community Park.
Lake Cumberland Luxury #2! Amazing Lake views, hot tub, fire pit!
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
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.
This charming cozy cottage has a private hot tub, deck for fishing.
Save an average of 15% on thousands of hotels when you're signed in
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 Library.
Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!
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.