Book Holiday Homes in Monticello

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Featured Holiday Homes in Monticello

Lake Retreat at Lake Cumberland Resort

Lake Retreat at Lake Cumberland Resort

Burnside
With a stay at this vacation home in Burnside, you'll be on a lake, and 23.3 mi (37.5 km) from Cumberland Falls and 9.1 mi (14.7 km) from Cumberland River.
Lake Retreat at Lake Cumberland Resort
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!
Boating Mecca: Near Dale Hollow Lake & Golf!

Boating Mecca: Near Dale Hollow Lake & Golf!

Burkesville
The price is AU$299 per night from 12 May to 13 May
AU$299
includes taxes & fees
12 May - 13 May
Located in Burkesville, this vacation home is on a lake, within a 10-minute drive of Dale Hollow Lake State Park and Dale Hollow Lake State Resort Park Golf ...
Boating Mecca: Near Dale Hollow Lake & Golf!
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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$659 per night from 29 Apr to 30 Apr
AU$659
includes taxes & fees
29 Apr - 30 Apr
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!
Hideaway 27

Hideaway 27

Helenwood
The price is AU$413 per night from 11 May to 12 May
AU$413
includes taxes & fees
11 May - 12 May
Located in Helenwood, this vacation home is in a rural location, within a 10-minute drive of Big South Fork Medical Center and Oneida City Park.
Hideaway 27
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
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
With a stay at this vacation home in Byrdstown, you'll be 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
Dale Hollow Cabin Next To State Park With Free Fire Pit & COVERED Boat Slip

Dale Hollow Cabin Next To State Park With Free Fire Pit & COVERED Boat Slip

Burkesville
Located in Burkesville, this vacation home is on a lake, within a 15-minute walk of Dale Hollow Lake State Park and Dale Hollow Lake State Resort Park Golf ...
Dale Hollow Cabin Next To State Park With Free Fire Pit & COVERED Boat Slip
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 Library.
6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍
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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
325 Holiday Homes
Lowest Price
AU$215
Highest Price
AU$659
Popular accommodation
Lake Retreat at Lake Cumberland Resort, Lake Cumberland Luxury #2! Amazing Lake views, hot tub, fire pit!, Boating Mecca: Near Dale Hollow Lake & Golf!, Luxe Lake Barndo w/ 2 King Suites! Hot Tub, Fire Pit, 1/8 mile to boat ramp!, Hideaway 27, Little blue house on the lake, Pool / Grill, Dale Hollow Lake and nearby Sunset Marina with Mountain view, Dale Hollow Cabin Next To State Park With Free Fire Pit & COVERED Boat Slip, 6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍

Top trending hotels in Monticello

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!
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.
Cumberland Belle Lakehouse 9 bedrm, 20 bed, 7 bath, swimspa/hotub&sauna

Cumberland Belle Lakehouse 9 bedrm, 20 bed, 7 bath, swimspa/hotub&sauna

Monticello
With a stay at this vacation home in Monticello, you'll be on a lake, and 8.2 mi (13.2 km) from Wayne County Historical Museum and 8.6 mi (13.9 km) from Wayne ...
Cumberland Belle Lakehouse 9 bedrm, 20 bed, 7 bath, swimspa/hotub&sauna
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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$215 per night from 29 Apr to 30 Apr
AU$215
includes taxes & fees
29 Apr - 30 Apr
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
Don't see what you're looking for?
See all available properties in Monticello
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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.

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^Subject to availability and chosen travel dates.