Book Holiday Homes in Monticello

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

Lake Retreat at Lake Cumberland Resort

Lake Retreat at Lake Cumberland Resort

Burnside
Stay at this vacation home in Burnside. Enjoy a garden, tennis courts, and patios. Popular attractions Natural Arch Scenic Area and Panoramic Trail are located ...
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
Book a stay at this family-friendly vacation home in Monticello. Enjoy free WiFi, a water park, and a garden. Popular attractions Firebrook Community Park and ...
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 NZ$322 per night from 27 Apr to 28 Apr
NZ$322
includes taxes & fees
27 Apr - 28 Apr
Stay at this vacation home in Burkesville. Enjoy free WiFi, a garden, and patios. Popular attractions Sulphur Creek Marina and Dale Hollow Lake State Resort ...
Boating Mecca: Near Dale Hollow Lake & Golf!
Save an average of 15% on thousands of hotels when you're signed in
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 NZ$826 per night from 8 Apr to 9 Apr
NZ$826
includes taxes & fees
8 Apr - 9 Apr
Book a stay at this family-friendly vacation home in Monticello. Enjoy free WiFi, a garden, and cable/satellite TV service. Popular attractions Wolf Creek Marina ...
Luxe Lake Barndo w/ 2 King Suites! Hot Tub, Fire Pit, 1/8 mile to boat ramp!
Hideaway 27

Hideaway 27

Helenwood
Stay at this vacation home in Helenwood. Enjoy free WiFi, a garden, and patios. Popular attractions Carter Lake and Oneida City Park are located nearby.
Hideaway 27
Little blue house on the lake

Little blue house on the lake

Nancy
Stay at this vacation home in Nancy. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Mill Springs Battlefield and Mill Springs Mill ...
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
Stay at this vacation home in Byrdstown. Enjoy free WiFi, private pools, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions ...
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
Stay at this vacation home in Burkesville. Enjoy free WiFi, patios, and cable/satellite TV service. Popular attractions Dale Hollow Reservoir and Dale Hollow ...
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
Book a stay at this family-friendly vacation home in Monticello. Enjoy free WiFi, private pools, and a garden. Popular attractions Firebrook Community Park and ...
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.

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
320 Holiday Homes
Lowest Price
NZ$241
Highest Price
NZ$826
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

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
Stay at this cottage in Monticello. Enjoy a water park, a garden, and tennis courts. Popular attractions Lake Cumberland Winery and Conley Bottom Marina are ...
This charming cozy cottage has a private hot tub, deck for fishing.
Lake Cumberland Luxury #2! Amazing Lake views, hot tub, fire pit!

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

Monticello
Book a stay at this family-friendly vacation home in Monticello. Enjoy free WiFi, a water park, and a garden. Popular attractions Firebrook Community Park and ...
Lake Cumberland Luxury #2! Amazing Lake views, hot tub, fire pit!
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 NZ$241 per night from 6 Apr to 7 Apr
NZ$241
includes taxes & fees
6 Apr - 7 Apr
Book a stay at this business-friendly hotel in Monticello. Enjoy free breakfast, free parking, and room service. Our guests praise the helpful staff and the ...
Best Western Lake Cumberland Inn
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
Book a stay at this family-friendly vacation home in Monticello. Enjoy free WiFi, a water park, and patios. Popular attractions Firebrook Community Park and ...
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.