Book Holiday Homes in Monticello

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Featured Holiday Homes in Monticello

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
Located in Monticello, this vacation home is within a 15-minute drive of Cumberland River and Burnside Library.
Opens in a new window6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more😍
Cumberland Lake House

Cumberland Lake House

Nancy
When you stay at this vacation home in Nancy, you'll be 7 minutes by car from Cumberland Point Recreation Area.
Opens in a new windowCumberland Lake House
Boating Mecca: Near Dale Hollow Lake & Golf!

Boating Mecca: Near Dale Hollow Lake & Golf!

Burkesville
The price is AU$271 per night from 8 Oct to 9 Oct
AU$271
8 Oct - 9 Oct
includes taxes & fees
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 ...
Opens in a new windowBoating Mecca: Near Dale Hollow Lake & Golf!
Save an average of 15% on thousands of hotels when you're signed in
3 miles from Wolf Creek Dam! Boat and camper parking available

3 miles from Wolf Creek Dam! Boat and camper parking available

Highway
Located in Albany, this vacation home is within a 15-minute drive of Wolf Creek National Fish Hatchery and Lake Cumberland State Resort Park.
Opens in a new window3 miles from Wolf Creek Dam! Boat and camper parking available
White Oak Cottage - Resort Pool, Boat Slip

White Oak Cottage - Resort Pool, Boat Slip

Burnside
The price is AU$597 per night from 1 Oct to 2 Oct
AU$597
1 Oct - 2 Oct
includes taxes & fees
With a stay at this vacation home in Somerset, you'll be on a lake, a 5-minute walk from Cumberland River and a 3-minute drive from Burnside Library.
Opens in a new windowWhite Oak Cottage - Resort Pool, Boat Slip
Cozy 2-bedroom house in Jamestown with AC, WiFi

Cozy 2-bedroom house in Jamestown with AC, WiFi

Jamestown
The price is AU$283 per night from 29 Sept to 30 Sept
AU$283
29 Sept - 30 Sept
includes taxes & fees
Located in Jamestown, this vacation home is within a 5-minute drive of Highland Manor Winery and Jamestown Town Hall.
Opens in a new windowCozy 2-bedroom house in Jamestown with AC, WiFi
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
Located in Monticello, this vacation home is on a lake, within a 15-minute drive of Cumberland River and Burnside Library.
Opens in a new window4 Bedrooms, Heated Private pool, hot tub, Game room, and Water Front View!
Cozy Lakehouse – Game Room, Pet-Friendly, Near Boatramp, 3-Season room!

Cozy Lakehouse – Game Room, Pet-Friendly, Near Boatramp, 3-Season room!

2 out of 5
Bronston
The price is AU$635 per night from 29 Sept to 30 Sept
AU$635
29 Sept - 30 Sept
includes taxes & fees
Located in Bronston, this vacation home is on the waterfront, a 1-minute drive from Cumberland River and 6 minutes from Burnside Library.
Opens in a new windowCozy Lakehouse – Game Room, Pet-Friendly, Near Boatramp, 3-Season room!
The Holiday Hutt at Dale Hollow Lake-Close to Sunset, Bball Court, Movie Theater

The Holiday Hutt at Dale Hollow Lake-Close to Sunset, Bball Court, Movie Theater

Monroe
The price is AU$3,389 per night from 26 Oct to 27 Oct
AU$3,389
26 Oct - 27 Oct
includes taxes & fees
Located in Byrdstown, this vacation home is on a lake, within a 15-minute drive of Dale Hollow Reservoir and Cordell Hull.
Opens in a new windowThe Holiday Hutt at Dale Hollow Lake-Close to Sunset, Bball Court, Movie Theater
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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
328 Holiday Homes
Lowest Price
AU$271
Highest Price
AU$3,389
Popular accommodation
6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more😍, Cumberland Lake House, Boating Mecca: Near Dale Hollow Lake & Golf!, 3 miles from Wolf Creek Dam! Boat and camper parking available, White Oak Cottage - Resort Pool, Boat Slip, Cozy 2-bedroom house in Jamestown with AC, WiFi, 4 Bedrooms, Heated Private pool, hot tub, Game room, and Water Front View!, Cozy Lakehouse – Game Room, Pet-Friendly, Near Boatramp, 3-Season room!, The Holiday Hutt at Dale Hollow Lake-Close to Sunset, Bball Court, Movie Theater

Top trending hotels in Monticello

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
Located in Monticello, this vacation home is within a 15-minute drive of Cumberland River and Burnside Library.
Opens in a new window6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more😍
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
Located in Monticello, this vacation home is on a lake, within a 15-minute drive of Cumberland River and Burnside Library.
Opens in a new window4 Bedrooms, Heated Private pool, hot tub, Game room, and Water Front View!
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.
Opens in a new windowLake 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
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.
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.