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
The price is NZ$895 per night from 3 Nov to 4 Nov
NZ$895
3 Nov - 4 Nov
includes taxes & fees
Book a stay at this family-friendly vacation home in Jamestown. Enjoy free WiFi, a water park, and a garden. Our guests praise the helpful staff in our reviews. ...
Opens in a new windowLAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.
Little blue house on the lake

Little blue house on the lake

Nancy
Stay at this vacation home in Nancy. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Mill Springs Battlefield and Mill Springs Mill Park ...
Opens in a new windowLittle blue house on the lake
4 Bedrooms, Heated Private pool, hot tub, Game room, and Water Front View!

4 Bedrooms, Heated Private pool, hot tub, Game room, and Water Front View!

Monticello
Book a stay at this family-friendly vacation home in Monticello. Enjoy free WiFi, private pools, and laundry facilities. Our guests praise the property condition ...
Opens in a new window4 Bedrooms, Heated Private pool, hot tub, Game room, and Water Front View!
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Cumberland Lake House

Cumberland Lake House

Nancy
Stay at this vacation home in Nancy. Enjoy laundry facilities, balconies, and an in-room coffeemaker. Popular attractions Cumberland Point Recreation Area and ...
Opens in a new windowCumberland Lake House
6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more😍

6 Bedroom home, heated 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 ...
Opens in a new window6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more😍
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 laundry facilities. Popular attractions Firebrook Community ...
Opens in a new windowLake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!
Lake Days & Starry Nights – Your Perfect Getaway Awaits

Lake Days & Starry Nights – Your Perfect Getaway Awaits

Burnside
Stay at this vacation home in Burnside. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Natural Arch Scenic Area and Panoramic Trail are ...
Opens in a new windowLake Days & Starry Nights – Your Perfect Getaway Awaits
Lakeview/Lakeside Lakehouse

Lakeview/Lakeside Lakehouse

Somerset
Stay at this vacation home in Somerset. Enjoy free WiFi, laundry facilities, and tennis courts. Popular attractions Cole Community Park and Burnside Library ...
Opens in a new windowLakeview/Lakeside Lakehouse
White Oak Cottage - Resort Pool, Boat Slip

White Oak Cottage - Resort Pool, Boat Slip

Burnside
The price is NZ$675 per night from 3 Nov to 4 Nov
NZ$675
3 Nov - 4 Nov
includes taxes & fees
Stay at this vacation home in Somerset. Enjoy free WiFi, a water park, and a garden. Popular attractions Cole Community Park and Burnside Library are located ...
Opens in a new windowWhite Oak Cottage - Resort Pool, Boat Slip
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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
297 Holiday Homes
Lowest Price
NZ$231
Highest Price
NZ$895
Popular accommodation
LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY., Little blue house on the lake, 4 Bedrooms, Heated Private pool, hot tub, Game room, and Water Front View!, Cumberland Lake House, 6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more😍, Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!, Lake Days & Starry Nights – Your Perfect Getaway Awaits, Lakeview/Lakeside Lakehouse, White Oak Cottage - Resort Pool, Boat Slip

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$231 per night from 5 Nov to 6 Nov
NZ$231
5 Nov - 6 Nov
includes taxes & fees
Book a stay at this business-friendly hotel in Monticello. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Opens in a new windowBest Western Lake Cumberland Inn
6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more😍

6 Bedroom home, heated 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 ...
Opens in a new window6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more😍
Large 8 Bedroom Home Overlooking Play Area, And Pool. Great For Family Reunions.

Large 8 Bedroom Home Overlooking Play Area, And Pool. Great For Family Reunions.

Monticello
Stay at this vacation home in Monticello. Enjoy a water park, a garden, and laundry facilities. Popular attractions Lake Cumberland Winery and Conley Bottom ...
Opens in a new windowLarge 8 Bedroom Home Overlooking Play Area, And Pool. Great For Family Reunions.
Save an average of 15% on thousands of hotels when you're signed in
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 laundry facilities. Popular attractions Lake Cumberland Winery and Conley Bottom Marina ...
Opens in a new windowThis charming cozy cottage has a private hot tub, deck for fishing.
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.

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