A winding fence on a grassy hill with horses grazing.

Monticello Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Monticello vacation rentals

A cozy living room with a sofa, coffee table, and a painting on the wall.

1. The Cozy Cabell Cottage

The Cozy Cabell Cottage
Monticello
9.8 out of 10, Exceptional, (56 reviews)
"Great clean place to stay with good parking. It was very quiet and felt safe as well. Would stay again. The host did an excellent job with making sure the place felt comfortable and convenient."
United States
tim w.
$174 nightly
The price is $191
Sep 1 - Sep 2
Total with taxes and fees
The Cozy Cabell Cottage

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

Lake Access ~ King Ensuites w/ fireplaces~ Hot Tub~ Fire Pit~ Boat Ramp
Monticello
10.0 out of 10, Exceptional, (39 reviews)
"Had such an amazing time in this beautiful home. Will definitely be back!"
United States
Monika H.
$533 nightly
The price is $572
Sep 1 - Sep 2
Total with taxes and fees
Lake Access ~ King Ensuites w/ fireplaces~ Hot Tub~ Fire Pit~ Boat Ramp
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

Lakeside Escape - Charming home centrally located on Lake Cumberland
Monticello
10.0 out of 10, Exceptional, (1 review)
"Clean house, pet friendly and our teens loved the game room"
United States
michelle d.
$245 nightly
The price is $270
Sep 1 - Sep 2
Total with taxes and fees
Lakeside Escape - Charming home centrally located on Lake Cumberland
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

Timy Home near Wolf Creek Marina & multiple boat ramps with a full kitchen
Nancy
9.4 out of 10, Exceptional, (41 reviews)
"Great place for cheap!"
United States
Jamie M.
$162 nightly
The price is $179
Sep 1 - Sep 2
Total with taxes and fees
Timy Home near Wolf Creek Marina & multiple boat ramps with a full kitchen
A compact kitchen with a black stove, white cabinets, a refrigerator, and a coffee maker.

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

Newly renovated near Rowena, Grider and Wolf Creek Dam
Albany
9.6 out of 10, Exceptional, (28 reviews)
"Great place to stay, property is very well maintained. Ample parking for truck and boat, highly recommend, will stay here again. "
United States
Trent N.
$184 nightly
The price is $203
Sep 3 - Sep 4
Total with taxes and fees
Newly renovated near Rowena, Grider and Wolf Creek Dam
A modern kitchen with wooden cabinets, a dining table, and a bench. There is a living area with a sofa and a coffee table.

6. Lake Cumberland "Lake Daze Cabin" near Clearwater

Lake Cumberland "Lake Daze Cabin" near Clearwater
Nancy
9.0 out of 10, Wonderful, (6 reviews)
"Place was great for just our weekend boating. Nice parking area. Little challenging to find just because building hidden by the storage facility. Also pull out couch was messed up so sleeking 5 worked but 6 wouldn’t have."
United States
Trevor
$200 nightly
The price is $220
Sep 1 - Sep 2
Total with taxes and fees
Lake Cumberland "Lake Daze Cabin" near Clearwater
A rectangular swimming pool with a tiled deck.

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

Private Cottage at Lake Cumberland Resort- a gated lakefront Community
Burnside
9.4 out of 10, Exceptional, (135 reviews)
"Nice and quiet, house super clean. Like being at home away from home."
United States
Paul R.
$319 nightly
The price is $352
Sep 1 - Sep 2
Total with taxes and fees
Private Cottage at Lake Cumberland Resort- a gated lakefront Community
A modern kitchen with white cabinets, a dining table with chairs, and a living area with a sofa and a TV.

8. New Near Jamestown Dock - A

New Near Jamestown Dock - A
Jamestown
9.6 out of 10, Exceptional, (27 reviews)
"The place was perfect for what we needed. It's right next to Pepe's and Giovanni's, two of my favorite Cumberland restaurants. It was also just 22 minutes from State Park Marina. You can hear everything from every room; we all went to bed and woke up at the same time, so it didn't bother us. I also loved the AC units in each room."
United States
Jennifer
$189 nightly
The price is $208
Sep 1 - Sep 2
Total with taxes and fees
New Near Jamestown Dock - A
A bedroom with a bed, nightstands, a TV, and a wall-mounted shelf.

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

Studio Cottage on the Square, entire rental unit in Jamestown, Kentucky
Jamestown
8.8 out of 10, Excellent, (13 reviews)
"Great location."
United States
Donald S.
$159 nightly
The price is $176
Sep 1 - Sep 2
Total with taxes and fees
Studio Cottage on the Square, entire rental unit in Jamestown, Kentucky
A cozy cabin interior with a wooden staircase, a living area with a sofa and coffee table, a kitchen with white cabinets and appliances, and a welcome sign on the wall.

10. NEW HOT TUB Cozy Cabin Cumberland River near Lake Cumberland~Firepit~New build

NEW HOT TUB Cozy Cabin Cumberland River near Lake Cumberland~Firepit~New build
Jamestown
9.2 out of 10, Wonderful, (19 reviews)
"Such a lovely property. Very cozy and inviting. We will definitely stay again."
United States
Jennifer S.
$318 nightly
The price is $349
Sep 1 - Sep 2
Total with taxes and fees
NEW HOT TUB Cozy Cabin Cumberland River near Lake Cumberland~Firepit~New build
A wooden cabin with a porch, a star emblem, and a 'No Shoes Nation' sign.

11. Cozy Cabin

Cozy Cabin
Burnside
9.2 out of 10, Wonderful, (14 reviews)
"It was an amazing stay very clean close to the river very relaxing"
United States
Jeremy C.
$197 nightly
The price is $217
Sep 1 - Sep 2
Total with taxes and fees
Cozy Cabin
A calm lake with a pebbly shore and dense forest in the background.

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

Wolf Creek Crossing Lake House Beach & Boat Launch .5 miles at Jabez Landing
Nancy
10.0 out of 10, Exceptional, (7 reviews)
"Host was wonderful and the place was fantastic!"
United States
Oliver C.
$272 nightly
The price is $299
Sep 2 - Sep 3
Total with taxes and fees
Wolf Creek Crossing Lake House Beach & Boat Launch .5 miles at Jabez Landing

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

CRISTY'S CABIN - cozy and quaint - where the deer and the ants play!
Burnside
9.6 out of 10, Exceptional, (10 reviews)
"The place is okay the cabin is nice but is dirty"
United States
Mohamed
$176 nightly
The price is $194
Sep 8 - Sep 9
Total with taxes and fees
CRISTY'S CABIN - cozy and quaint - where the deer and the ants play!
A cozy room with a floral sofa, a TV, and a sign that reads "Everglow Hollow".

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

LAKE CUMBERLAND Get-a-Way! Charming House. BOAT RAMP NEARBY - Wifi - RV Hookups
Faubush
9.8 out of 10, Exceptional, (7 reviews)
"Everglow Hollow was great! We stayed for a long weekend and it was the perfect place to relax, while not being too far away from Lake Cumberland. Host also responded to questions right away and were very helpful. "
Canada
Morgan P.
$246 nightly
The price is $271
Sep 7 - Sep 8
Total with taxes and fees
LAKE CUMBERLAND Get-a-Way! Charming House. BOAT RAMP NEARBY - Wifi - RV Hookups
A modern two-story house with a wooden exterior, a balcony on the upper floor, and a garage door.

15. Cordial chalet with a balcony to have coffee with the squirrels

Cordial chalet with a balcony to have coffee with the squirrels
Somerset
9.8 out of 10, Exceptional, (21 reviews)
"Beautiful house in a nice location. Very clean also"
United States
Julia
$170 nightly
The price is $187
Sep 1 - Sep 2
Total with taxes and fees
Cordial chalet with a balcony to have coffee with the squirrels
A wooden interior with a wooden door, a wreath, a small table, and a vase of flowers.

16. Avery Acres

Avery Acres
Albany
9.4 out of 10, Exceptional, (6 reviews)
"The host was awesome - excellent communication and customer service. The house was extremely clean, well equipped, and roomy. The bed was comfortable. We had everything that we needed! We will definitely stay at Avery Acres again. Recommend it!"
United States
Kandy F.
$211 nightly
The price is $233
Sep 1 - Sep 2
Total with taxes and fees
Avery Acres
A clear river with rocks, surrounded by trees and a grassy area.

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

Unique Hexagon Cottage Atop Marina · Boat Parking · 3 En Suite Baths · Pets okay
Jamestown
10.0 out of 10, Exceptional, (214 reviews)
"We felt like we were at home! Very clean and comfortable home with everything we needed. Communication with the host was flawless. This was my families first trip to Lake Cumberland and it was everything we thought it would be. Beautiful lake! We will definitely be coming back and staying at the Hexagon cottage again."
United States
Joleen
$355 nightly
The price is $391
Sep 1 - Sep 2
Total with taxes and fees
Unique Hexagon Cottage Atop Marina · Boat Parking · 3 En Suite Baths · Pets okay
A modern kitchen with dark cabinets, a central island with stools, stainless steel appliances, and pendant lighting.

18. Lake Cabin, Fishing Access, swimming, walk to lake, boat parking, fenced yard!

Lake Cabin, Fishing Access, swimming, walk to lake, boat parking, fenced yard!
Nancy
10.0 out of 10, Exceptional, (6 reviews)
"We loved our stay while at Cumberland. This is a great place to stay just as described. We will definitely book again. "
United States
Tricia H.
$352 nightly
The price is $388
Sep 1 - Sep 2
Total with taxes and fees
Lake Cabin, Fishing Access, swimming, walk to lake, boat parking, fenced yard!
A covered outdoor deck with a table and chairs, surrounded by a wooden railing, overlooking a grassy area with trees.

19. Lake Cumberland Cabin

Lake Cumberland Cabin
Bronston
9.8 out of 10, Exceptional, (17 reviews)
"No complaints for this stay"
United States
Trisha E.
$259 nightly
The price is $286
Sep 1 - Sep 2
Total with taxes and fees
Lake Cumberland Cabin
A wooden deck with a ceiling fan, a brick wall, and a view of a forest.

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

Charming 1-bedroom fish shack in Somerset with WiFi and AC
Somerset
9.8 out of 10, Exceptional, (17 reviews)
"Property was perfect for our needs, very close to restaurants and shops. Very well maintained Would absolutely stay again.."
United States
David W.
$133 nightly
The price is $146
Sep 1 - Sep 2
Total with taxes and fees
Charming 1-bedroom fish shack in Somerset with WiFi and AC
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.
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Top Monticello Hotel Reviews

Lake Bluff Paradise on Lake Cumberland. Game Room and seasonal Hot Tub!

Lake Bluff Paradise on Lake Cumberland. Game Room and seasonal Hot Tub!

10/10 Excellent
"We had a shot two night stay for my bachelor trip. It was awesome great view of the lake with a fun game room to keep us entertained."
Josh B. 2-night trip
Posted 14 hours ago
Lake Bluff Paradise on Lake Cumberland. Game Room and seasonal Hot Tub!

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 $194 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 45 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.