Book Holiday Homes in Monticello

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Featured Holiday Homes in Monticello

Lake Days & Starry Nights – Your Perfect Getaway Awaits

Lake Days & Starry Nights – Your Perfect Getaway Awaits

Burnside KY
Stay at this holiday home in Burnside. Enjoy free Wi-Fi, 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
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 KY
The price is NZ$979 per night from 4 May to 5 May
NZ$979
4 May - 5 May
includes taxes & fees
Stay at this family-friendly holiday home in Jamestown. Enjoy free Wi-Fi, a garden and laundry facilities. Our guests praise the helpful staff in their reviews. ...
Opens in a new windowLAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.

Welcome to the your budget friendly  stop right off the highway 27.

Welcome to the your budget friendly stop right off the highway 27.

Somerset KY
The price is NZ$207 per night from 4 May to 5 May
NZ$207
4 May - 5 May
includes taxes & fees
Stay at this holiday home in Somerset. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Somerset Mall and Cole Community Park are located ...
Opens in a new window Welcome to the your budget friendly stop right off the highway 27.
Save an average of 15% on thousands of hotels when you're signed in
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 KY
Stay at this family-friendly holiday home in Monticello. Enjoy free Wi-Fi, private pools and laundry facilities. Our guests praise the property condition in ...
Opens in a new window4 Bedrooms, Heated Private pool, hot tub, Game room, and Water Front View!
Ellie's Place-"Wow, this is nice!"

Ellie's Place-"Wow, this is nice!"

Burnside KY
Stay at this holiday home in Burnside. Enjoy free Wi-Fi, laundry facilities and a pool table. Popular attractions Natural Arch Scenic Area and Panoramic Trail ...
Opens in a new windowEllie's Place-"Wow, this is nice!"
Amazing 5BR House with Lake & Mountain Views in Gated Resort

Amazing 5BR House with Lake & Mountain Views in Gated Resort

Burnside KY
Stay at this holiday home in Burnside. Enjoy free Wi-Fi, laundry facilities and tennis courts. Popular attractions Natural Arch Scenic Area and Panoramic Trail ...
Opens in a new windowAmazing 5BR House with Lake & Mountain Views in Gated Resort
Charming 1-bedroom fish shack in Somerset with WiFi and AC

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

Somerset KY
The price is NZ$248 per night from 4 May to 5 May
NZ$248
4 May - 5 May
includes taxes & fees
Stay at this holiday home in Somerset. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Trinity Park and The Center For Rural Development ...
Opens in a new windowCharming 1-bedroom fish shack in Somerset with WiFi and AC
Cumberland Lake House

Cumberland Lake House

Nancy KY
Stay at this holiday home in Nancy. Enjoy laundry facilities, balconies and an in-room coffee maker. Popular attractions Cumberland Point Recreation Area and ...
Opens in a new windowCumberland Lake House
“Red’s House” located in Oneida city limits

“Red’s House” located in Oneida city limits

Oneida TN
Stay at this holiday home in Oneida. Enjoy laundry facilities, patios and an in-room coffee maker. Popular attractions Field at Oneida City Park and Oneida City ...
Opens in a new window“Red’s House” located in Oneida city limits
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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
316 Holiday Homes
Lowest Price
NZ$207
Highest Price
NZ$979
Popular accommodation
Lake Days & Starry Nights – Your Perfect Getaway Awaits, LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY., Welcome to the your budget friendly stop right off the highway 27., 4 Bedrooms, Heated Private pool, hot tub, Game room, and Water Front View!, Ellie's Place-"Wow, this is nice!", Amazing 5BR House with Lake & Mountain Views in Gated Resort, Charming 1-bedroom fish shack in Somerset with WiFi and AC, Cumberland Lake House, “Red’s House” located in Oneida city limits

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$224 per night from 4 May to 5 May
NZ$224
4 May - 5 May
includes taxes & fees
Stay at this business-friendly hotel in Monticello. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
Opens in a new windowBest 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 KY
Stay at this cottage in Monticello. Enjoy a garden, laundry facilities and tennis courts. 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.
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 KY
Stay at this family-friendly holiday home in Monticello. Enjoy free Wi-Fi, private pools and a garden. Popular attractions Firebrook Community Park and Potato ...
Opens in a new window6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more😍
Save an average of 15% on thousands of hotels when you're signed in
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 KY
Stay at this family-friendly holiday home in Monticello. Enjoy free Wi-Fi, private pools and laundry facilities. Our guests praise the property condition in ...
Opens in a new window4 Bedrooms, Heated Private pool, hot tub, Game room, and Water Front View!
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.