Monticello Holiday Rentals from NZ$424: Search Short-Term Rentals

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Our top choices for Monticello holiday rentals

A kitchen with white cabinets, a microwave, a stove, a sink, and a dishwasher.

1. Main St Monticello-Lake Cumberland Shenanigans

Monticello

includes taxes & fees

22 Nov - 23 Nov

A hot tub with a woman relaxing, surrounded by plants and candles, set on a wooden deck with a forest view.

2. Lake Access ~ King Ensuites w/ fireplaces~ Hot Tub~ Fire Pit~ Boat Ramp

Monticello

Lindsey R.

includes taxes & fees

16 Nov - 17 Nov

A modern kitchen with wooden cabinets, stainless steel appliances, and a central island with bar stools.

3. Lakeside Escape - Charming home centrally located on Lake Cumberland

Monticello

michelle d.

includes taxes & fees

15 Nov - 16 Nov

A kitchen with a stainless steel refrigerator, a coffee maker, and a trash bin.

4. Timy Home near Wolf Creek Marina & multiple boat ramps with a full kitchen

Nancy

Joey A.

includes taxes & fees

17 Nov - 18 Nov

A modern kitchen with wooden cabinets, a dining table, and a bench. There is a living area with a sofa and a coffee table.

5. Lake Cumberland "Lake Daze Cabin" near Clearwater

Nancy

Trevor

includes taxes & fees

15 Nov - 16 Nov

A modern kitchen with white cabinets, a dining table with chairs, and a living area with a sofa and a TV.

6. New Near Jamestown Dock - A

Jamestown

Venus W.

includes taxes & fees

15 Nov - 16 Nov

A building with a black front door, stone steps, and a wooden deck.

7. Cozy 1-bedroom house near lake Cumberland

Faubush

includes taxes & fees

6 Dec - 7 Dec

A cozy room with a floral sofa, a TV, and a sign that reads "Everglow Hollow".

8. LAKE CUMBERLAND Get-a-Way! Charming House. BOAT RAMP NEARBY - Wifi - RV Hookups

Faubush

Morgan P.

includes taxes & fees

16 Nov - 17 Nov

A wooden cabin with a porch, a star emblem, and a 'No Shoes Nation' sign.

9. Cozy Cabin

Burnside

angela j.

includes taxes & fees

15 Nov - 16 Nov

A natural landscape with a clear water body, rocky shore, and dense forest.

10. Lovely 2-bedroom cabin with AC in peaceful Whitley City

Whitley City

Shelby T.

includes taxes & fees

7 Dec - 8 Dec

A compact kitchen with a microwave, refrigerator, and stove, a small trash bin, and a seating area with a bench.

11. Knotty Acres Lake Cumberland Basecamp

Albany

Scott M.

includes taxes & fees

15 Nov - 16 Nov

A compact kitchen with a black stove, white cabinets, a refrigerator, and a coffee maker.

12. Newly renovated near Rowena, Grider and Wolf Creek Dam

Albany

Louise W.

includes taxes & fees

17 Nov - 18 Nov

A living room with a sofa, armchair, television, and decorative items.

13. Cute and Quaint!

Albany

Randy J.

includes taxes & fees

17 Nov - 18 Nov

A modern house with a wooden deck, large windows, and a chimney.

14. Cozy 3 bedroom A frame-cabin in beautiful Nancy KY, overlooking Lake Cumberland!

Nancy

includes taxes & fees

20 Nov - 21 Nov

A bedroom with a bed, nightstands, a TV, and a wall-mounted shelf.

15. Studio Cottage on the Square, entire rental unit in Jamestown, Kentucky

Jamestown

Jessica R.

includes taxes & fees

16 Nov - 17 Nov

16. CRISTY'S CABIN - cozy and quaint - where the deer and the ants play!

Burnside

Chelsie S.

includes taxes & fees

17 Nov - 18 Nov

A hot tub in a wooden cabin with a view of the forest.

17. Private Cottage at Lake Cumberland Resort- a gated lakefront Community

Burnside

Nancy D.

includes taxes & fees

17 Nov - 18 Nov

A wooden interior with a wooden door, a wreath, a small table, and a vase of flowers.

18. Avery Acres

Albany

Josh W.

includes taxes & fees

26 Nov - 27 Nov

A hot tub with a view of a forested area.

19. Cozy 2-Bedroom Cabin Overlooking Beautiful Lake Cumberland

Nancy

kashyap p.

includes taxes & fees

16 Nov - 17 Nov

A modern kitchen with white cabinetry, a dining table with chairs, a refrigerator, and an air conditioning unit.

20. Cozy, private, 1-bedroom cabin in Monroe, near Livingston, Dale Hollow Lake

Monroe

Anonymous traveller

includes taxes & fees

29 Nov - 30 Nov

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Top Monticello Hotel Reviews

Best Western Lake Cumberland Inn

10/10 Excellent

"We ALWAYS stay here when we travel from Indiana to Monticello to visit family. I wouldn’t go anywhere else. The staff are the nicest most helpful people. Now, their breakfast is gross. Eggs are fake, bacon is 🤮 (probably also fake). Their waffles are good though. But for someone who has diabetes we need the protein."

6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more

10/10 Excellent

"We enjoyed the amenities. My kiddos loved playing pool, basketball and the arcade game. I was blown away with all the restrooms. Great remodeling ideas when i get hom. We will definitely revisit in the spring/summer so we can enjoy the pool. The hot tub was a great bonus for the cool fall days."

Lake Bluff Paradise on Lake Cumberland. Game Room and Hot Tub Sept 15-May 15!

10/10 Excellent

"Stunning view of the lake from screened in porch, lower deck hot tub and swing.Lovely accomodations, well stocked with necessities for cooking and eating in. Woudl definitely stay again!"

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

10/10 Excellent

"Our group spent a beautiful fall weekend in this beautiful home in a gorgeous setting overlooking the lake. The kitchen was the best stocked kitchen of any we’ve ever rented! Plenty of cookware for all our meals together. The hot tub was a nice relaxing addition for an afternoon soak. All the bedrooms were spacious and comfortable for each couple and the living spaces were uber comfy and just right. And the home was close enough for day trips for kayaking on the lane and hiking at Cumberland State Park. Highly recommend All of this!. We’ll be back!"

Find out more about Monticello

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Monticello holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Monticello. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Monticello. Seeing all the best attractions is bound to make you fall in love with Monticello. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Monticello short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Monticello?

Yes, there are holiday rentals close to the most popular sights in Monticello, or you can select a more secluded option if you're looking for a relaxing stay. Discover why Monticello is known for its marina and lakeside. Make sure you have time to check out the basketball games and wineries during your trip.

What are some of the best holiday rentals that Monticello has to offer?

6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more: This highly rated holiday home rental in Monticello offers an outdoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. Other favourite homes for rent in Monticello are 4 Bedrooms, Heated Private pool, hot tub, Game room, and Water Front View! and Large 8 Bedroom Home Overlooking Play Area, And Pool. Great For Family Reunions..

How many holiday rentals are there in Monticello?

With 47 Expedia holiday rentals, you're guaranteed to find just the right place for your Monticello stay.

What’s there to see and do in Monticello?

Cumberland River and Mill Springs Mill Park are a couple of scenic spots to enjoy the outdoors, whereas Wayne County Historical Museum is one of the cultural attractions. While here, Conley Bottom Marina and Lake Cumberland Winery are other places worth a visit.

What’s a holiday rental in Monticello like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Monticello. Holiday rentals feature extras like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy front desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for family trips.

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Check prices for these dates

Our top choices for Monticello holiday rentals

1. Main St Monticello-Lake Cumberland Shenanigans

2. Lake Access ~ King Ensuites w/ fireplaces~ Hot Tub~ Fire Pit~ Boat Ramp

3. Lakeside Escape - Charming home centrally located on Lake Cumberland

4. Timy Home near Wolf Creek Marina & multiple boat ramps with a full kitchen

5. Lake Cumberland "Lake Daze Cabin" near Clearwater

6. New Near Jamestown Dock - A

7. Cozy 1-bedroom house near lake Cumberland

8. LAKE CUMBERLAND Get-a-Way! Charming House. BOAT RAMP NEARBY - Wifi - RV Hookups

9. Cozy Cabin

10. Lovely 2-bedroom cabin with AC in peaceful Whitley City

11. Knotty Acres Lake Cumberland Basecamp

12. Newly renovated near Rowena, Grider and Wolf Creek Dam

13. Cute and Quaint!

14. Cozy 3 bedroom A frame-cabin in beautiful Nancy KY, overlooking Lake Cumberland!

15. Studio Cottage on the Square, entire rental unit in Jamestown, Kentucky

16. CRISTY'S CABIN - cozy and quaint - where the deer and the ants play!

17. Private Cottage at Lake Cumberland Resort- a gated lakefront Community

18. Avery Acres

19. Cozy 2-Bedroom Cabin Overlooking Beautiful Lake Cumberland

20. Cozy, private, 1-bedroom cabin in Monroe, near Livingston, Dale Hollow Lake

Find holiday rentals that suit your style

Top Monticello Hotel Reviews

Best Western Lake Cumberland Inn

Quality Inn & Suites Somerset

Cumberland Falls State Resort Park

Dale Hollow Lake State Resort Park

Courtyard by Marriott Somerset

6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more

Royal Inn

Lake Bluff Paradise on Lake Cumberland. Game Room and Hot Tub Sept 15-May 15!

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

Find out more about Monticello

Frequently asked questions

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