Book Holiday Homes in Monticello

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Featured Holiday Homes in Monticello

LOG Cabin, 5 miles from town, but very country setting

LOG Cabin, 5 miles from town, but very country setting

Science Hill
Book a stay at this family-friendly vacation home in Somerset. Enjoy free WiFi, a water park, and a garden. Popular attraction SomerSplash is located ...
LOG Cabin, 5 miles from town, but very country setting
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
Book a stay at this family-friendly vacation home in Monticello. Enjoy a garden, cable/satellite TV service, and an in-room coffeemaker. Popular attractions ...
Luxe Lake Barndo w/ 2 King Suites! Hot Tub, Fire Pit, 1/8 mile to boat ramp!
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 Burnside Marina and Zollicoffer ...
6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍
Save an average of 15% on thousands of hotels when you're signed in
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 Lake Cumberland Winery and Zollicoffer Park are ...
Little blue house on the lake
"Shore Thing", Cozy Lake Cumberland Cabin - Hot Tub, Fire Pit, Minutes from Lake

"Shore Thing", Cozy Lake Cumberland Cabin - Hot Tub, Fire Pit, Minutes from Lake

Nancy
Stay at this vacation home in Nancy. Enjoy patios, an in-room coffeemaker, and in-room fireplaces. Popular attraction Lake Cumberland Winery is located ...
"Shore Thing", Cozy Lake Cumberland Cabin - Hot Tub, Fire Pit, Minutes from Lake
Near Cumberland River, 12 miles from Wolf Creek Dam, in Creelsboro community

Near Cumberland River, 12 miles from Wolf Creek Dam, in Creelsboro community

Jamestown
Stay at this vacation home in Jamestown. Enjoy cable/satellite TV service, an in-room coffeemaker, and in-room fireplaces. Popular attraction Wolf Creek National ...
Near Cumberland River, 12 miles from Wolf Creek Dam, in Creelsboro community
Lake Cumberland Ohana.  Kid friendly, best views, hot tub.

Lake Cumberland Ohana. Kid friendly, best views, hot tub.

Burnside
Book a stay at this family-friendly vacation home in Burnside. Enjoy free WiFi, tennis courts, and patios. Popular attractions Natural Arch Scenic Area and Burnside ...
Lake Cumberland Ohana. Kid friendly, best views, hot tub.
Captivating 2-bedroom, garage door house with WiFi, AC in welcoming Somerset

Captivating 2-bedroom, garage door house with WiFi, AC in welcoming Somerset

2 out of 5
Somerset
The price is NZ$283 per night from 2 Jan to 3 Jan
NZ$283
includes taxes & fees
2 Jan - 3 Jan 2025
Stay at this vacation home in Somerset. Enjoy free WiFi, a garden, and patios. Popular attractions The Center For Rural Development and Pulaski County Park are ...
Captivating 2-bedroom, garage door house with WiFi, AC in welcoming Somerset
Charming 1-bedroom fish shack in Somerset with WiFi and AC

Charming 1-bedroom fish shack in Somerset with WiFi and AC

2 out of 5
Somerset
The price is NZ$263 per night from 29 Dec to 30 Dec
NZ$263
includes taxes & fees
29 Dec - 30 Dec
Stay at this vacation home in Somerset. Enjoy free WiFi, a garden, and patios. Popular attractions The Center For Rural Development and Pulaski County Park are ...
Charming 1-bedroom fish shack in Somerset with WiFi and AC
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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
256 Holiday Homes
Lowest Price
NZ$205
Highest Price
NZ$283
Popular accommodation
LOG Cabin, 5 miles from town, but very country setting, Luxe Lake Barndo w/ 2 King Suites! Hot Tub, Fire Pit, 1/8 mile to boat ramp!, 6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍 , Little blue house on the lake, "Shore Thing", Cozy Lake Cumberland Cabin - Hot Tub, Fire Pit, Minutes from Lake, Near Cumberland River, 12 miles from Wolf Creek Dam, in Creelsboro community, Lake Cumberland Ohana. Kid friendly, best views, hot tub., Captivating 2-bedroom, garage door house with WiFi, AC in welcoming Somerset , Charming 1-bedroom fish shack in Somerset with WiFi and AC

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 NZ$205 per night from 29 Dec to 30 Dec
NZ$205
includes taxes & fees
29 Dec - 30 Dec
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
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 attraction Lake Cumberland Winery is located nearby.
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
Book a stay at this family-friendly vacation home in Monticello. Enjoy free WiFi, a water park, and patios. Popular attractions Burnside Marina and Zollicoffer ...
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
Book a stay at this family-friendly vacation home in Monticello. Enjoy free WiFi, private pools, and a garden. Popular attractions Burnside Marina and Zollicoffer ...
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.

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