Monticello Vacation Rentals from $246: Search Short-Term Rentals

Q: Can I find a vacation rental in Monticello?

Yes, we offer vacation rentals close to top points of interest in Monticello, or you can choose a 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.

Q: What are some of the best vacation rentals that Monticello has to offer?

6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more : Visitors like this Monticello vacation home rental. It offers an outdoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation. Other favorite 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. .

Q: How many vacation rentals are there in Monticello?

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

Q: 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.

Q: What’s a vacation rental in Monticello like?

A vacation rental is a private property you can book for several days or longer in Monticello. Vacation rentals offer amenities like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a clean environment, a vacation rental can offer a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for small groups.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Monticello vacation rentals

1. Main St Monticello-Lake Cumberland Shenanigans

Monticello

$129 nightly

Nov 12 - Nov 13

Total with taxes and fees

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.

$565 nightly

Nov 17 - Nov 18

Total with taxes and fees

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.

$223 nightly

Nov 12 - Nov 13

Total with taxes and fees

A modern kitchen with white cabinets, a stainless steel stove, a sink, and a countertop.

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

Nancy

Joey A.

$174 nightly

Dec 10 - Dec 11

Total with taxes and fees

A fire pit with two wooden chairs, surrounded by a stone wall and a wooden fence.

5. Unique Hexagon Cottage Atop Marina · Boat Parking · 3 En Suite Baths · Pets okay

Jamestown

Jennifer S.

$377 nightly

Dec 1 - Dec 2

Total with taxes and fees

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

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

Faubush

Morgan P.

$208 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

7. Lake Cumberland "Lake Daze Cabin" near Clearwater

Nancy

Trevor

$184 nightly

Nov 12 - Nov 13

Total with taxes and fees

A modern kitchen with white cabinets, stainless steel appliances, and a dining area with a wooden table and white chairs.

8. Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!

Jamestown

ashley k.

$433 nightly

Nov 12 - Nov 13

Total with taxes and fees

A hot tub with a view of a forested area.

9. Cozy 2-Bedroom Cabin Overlooking Beautiful Lake Cumberland

Nancy

kashyap p.

$226 nightly

Nov 12 - Nov 13

Total with taxes and fees

A cozy living room with a sofa, a coffee table, and a TV. There is a kitchen with wooden cabinets and a bar area.

10. Country Comfort on Lake Cumberland!! 5 miles from Marina Rowena; Lake Cumberland

Albany

Eric G.

$277 nightly

Nov 12 - Nov 13

Total with taxes and fees

A rural landscape with a small house, a pond, and trees.

11. Lake Cumberland Pond View

Russell Springs

Kevin K.

$348 nightly

Nov 17 - Nov 18

Total with taxes and fees

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

12. Avery Acres

Albany

Josh W.

$205 nightly

Nov 12 - Nov 13

Total with taxes and fees

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

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

Jamestown

Jessica R.

$145 nightly

Nov 16 - Nov 17

Total with taxes and fees

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

Burnside

Chelsie S.

$146 nightly

Nov 16 - Nov 17

Total with taxes and fees

A covered outdoor seating area with chairs and a table, surrounded by a forested landscape.

15. Harbor Hideway is a cozy, romantic gem minutes away from Jamestown Marina!

Jamestown

Lena R.

$433 nightly

Nov 12 - Nov 13

Total with taxes and fees

A wooden deck with a swing chair, a bench, and a table with chairs. There are potted plants and a sign on the wall.

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

Whitley City

Shelby T.

$246 nightly

Nov 12 - Nov 13

Total with taxes and fees

A wooden deck with a railing overlooking a forested area.

17. New Rustic Home Near State Dock

Jamestown

Ashley D.

$296 nightly

Nov 21 - Nov 22

Total with taxes and fees

A porch with two wicker chairs, a wooden railing, and a patterned rug.

18. Lake Daze, Blue Cottage <1mile to Jamestown Marina with space to trailer boat.

Jamestown

Emily W.

$353 nightly

Nov 12 - Nov 13

Total with taxes and fees

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

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

Albany

Louise W.

$174 nightly

Nov 12 - Nov 13

Total with taxes and fees

A wooden porch with a white door, a cushion, a small table, and a wreath.

20. Wolf Creek Crossing Lake House Beach & Boat Launch .5 miles at Jabez Landing

Nancy

Brittany S.

$274 nightly

Dec 7 - Dec 8

Total with taxes and fees

View all properties

Find vacation rentals that suit your style

Cabins

Private vacation homes

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Monticello Hotel Reviews

Best Western Lake Cumberland Inn

10/10 Excellent

"Overall, the property is well-maintained and clean. I did notice little things in our room like the bathroom toilet leaked and the light above the sink was out. Other than that no complaints."

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!"

Find out more about Monticello

Everything you need to know about Monticello vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Monticello vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Monticello vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Monticello vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Monticello. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Monticello in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $246 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Monticello rentals

At Expedia, we put the best Monticello vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Monticello rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Monticello vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Monticello. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Monticello?

Yes, we offer vacation rentals close to top points of interest in Monticello, or you can choose a 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 vacation rentals that Monticello has to offer?

6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more: Visitors like this Monticello vacation home rental. It offers an outdoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation. Other favorite 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 vacation rentals are there in Monticello?

With 47 Expedia vacation rentals, you're sure 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 vacation rental in Monticello like?

A vacation rental is a private property you can book for several days or longer in Monticello. Vacation rentals offer amenities like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a clean environment, a vacation rental can offer a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for small groups.

Monticello Vacation Rentals

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Monticello vacation 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. Unique Hexagon Cottage Atop Marina · Boat Parking · 3 En Suite Baths · Pets okay

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

7. Lake Cumberland "Lake Daze Cabin" near Clearwater

8. Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!

9. Cozy 2-Bedroom Cabin Overlooking Beautiful Lake Cumberland

10. Country Comfort on Lake Cumberland!! 5 miles from Marina Rowena; Lake Cumberland

11. Lake Cumberland Pond View

12. Avery Acres

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

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

15. Harbor Hideway is a cozy, romantic gem minutes away from Jamestown Marina!

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

17. New Rustic Home Near State Dock

18. Lake Daze, Blue Cottage <1mile to Jamestown Marina with space to trailer boat.

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

20. Wolf Creek Crossing Lake House Beach & Boat Launch .5 miles at Jabez Landing

Find vacation rentals that suit your style

Top Monticello Hotel Reviews

Best Western Lake Cumberland Inn

Find out more about Monticello

Explore a world of travel with Expedia

Frequently asked questions

Expedia's Latest Trends

Go further with the Expedia app