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
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Monticello vacation rentals

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

1. Main St Monticello-Lake Cumberland Shenanigans

Main St Monticello-Lake Cumberland Shenanigans
Monticello
$290 nightly
The price is $320
Nov 16 - Nov 17
Total with taxes and fees
Main St Monticello-Lake Cumberland Shenanigans
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

Lake Access ~ King Ensuites w/ fireplaces~ Hot Tub~ Fire Pit~ Boat Ramp
Monticello
10.0 out of 10, Exceptional, (43 reviews)
"The house was beautiful! Everything was great and exactly as described! We had a great family weekend!"
United States
Lindsey R.
$565 nightly
The price is $606
Nov 16 - Nov 17
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, (2 reviews)
"Clean house, pet friendly and our teens loved the game room"
United States
michelle d.
$223 nightly
The price is $246
Nov 16 - Nov 17
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, (47 reviews)
"It was great"
United States
Joey A.
$165 nightly
The price is $182
Nov 17 - Nov 18
Total with taxes and fees
Timy Home near Wolf Creek Marina & multiple boat ramps with a full kitchen
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

Lake Cumberland "Lake Daze Cabin" near Clearwater
Nancy
9.2 out of 10, Wonderful, (7 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
$183 nightly
The price is $202
Nov 16 - Nov 17
Total with taxes and fees
Lake Cumberland "Lake Daze Cabin" near Clearwater
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

New Near Jamestown Dock - A
Jamestown
9.6 out of 10, Exceptional, (32 reviews)
"Perfect stay, bed was so comfortable. Patios to enjoy the evenings. Clean and was exactly as it was described. We have stayed in other properties of Heather and never have been disappointed."
United States
Venus W.
$179 nightly
The price is $197
Nov 16 - Nov 17
Total with taxes and fees
New Near Jamestown Dock - A
A building with a black front door, stone steps, and a wooden deck.

7. Cozy 1-bedroom house near lake Cumberland

Cozy 1-bedroom house near lake Cumberland
Faubush
$189 nightly
The price is $208
Dec 2 - Dec 3
Total with taxes and fees
Cozy 1-bedroom house near lake Cumberland
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

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.
$208 nightly
The price is $229
Nov 16 - Nov 17
Total with taxes and fees
LAKE CUMBERLAND Get-a-Way! Charming House. BOAT RAMP NEARBY - Wifi - RV Hookups
A wooden cabin with a porch, a star emblem, and a 'No Shoes Nation' sign.

9. Cozy Cabin

Cozy Cabin
Burnside
9.2 out of 10, Wonderful, (15 reviews)
"Very clean"
United States
angela j.
$188 nightly
The price is $207
Nov 16 - Nov 17
Total with taxes and fees
Cozy Cabin
A natural landscape with a clear water body, rocky shore, and dense forest.

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

Lovely 2-bedroom cabin with AC in peaceful Whitley City
Whitley City
10.0 out of 10, Exceptional, (1 review)
"Very nice stay and nice hosts!"
United States
Shelby T.
$246 nightly
The price is $271
Nov 17 - Nov 18
Total with taxes and fees
Lovely 2-bedroom cabin with AC in peaceful Whitley City
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

Knotty Acres Lake Cumberland Basecamp
Albany
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful location, super close to Lake Cumberland. Host was extremely helpful & communicative. Could not have asked for a better experience!"
United States
Scott M.
$280 nightly
The price is $309
Nov 16 - Nov 17
Total with taxes and fees
Knotty Acres Lake Cumberland Basecamp
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

Newly renovated near Rowena, Grider and Wolf Creek Dam
Albany
9.6 out of 10, Exceptional, (37 reviews)
"Perfect for what we needed!Very clean and comfortable!Host was very nice and communicated effectively!"
United States
Louise W.
$174 nightly
The price is $192
Nov 17 - Nov 18
Total with taxes and fees
Newly renovated near Rowena, Grider and Wolf Creek Dam
A living room with a sofa, armchair, television, and decorative items.

13. Cute and Quaint!

Cute and Quaint!
Albany
9.6 out of 10, Exceptional, (8 reviews)
"We had no problems and found things to exceed our expectations!"
United States
Randy J.
$159 nightly
The price is $175
Nov 16 - Nov 17
Total with taxes and fees
Cute and Quaint!
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!

Cozy 3 bedroom A frame-cabin in beautiful Nancy KY, overlooking Lake Cumberland!
Nancy
$264 nightly
The price is $291
Nov 22 - Nov 23
Total with taxes and fees
Cozy 3 bedroom A frame-cabin in beautiful Nancy KY, overlooking Lake Cumberland!
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

Studio Cottage on the Square, entire rental unit in Jamestown, Kentucky
Jamestown
8.4 out of 10, Very good, (15 reviews)
"Place was very clean and had everything we needed for our weekend stay!"
United States
Jessica R.
$131 nightly
The price is $144
Nov 16 - Nov 17
Total with taxes and fees
Studio Cottage on the Square, entire rental unit in Jamestown, Kentucky
Trees on all sides

16. 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
9.0 out of 10, Wonderful, (14 reviews)
"The cabin is beautiful and worth the stay!"
United States
Chelsie S.
$156 nightly
The price is $172
Nov 17 - Nov 18
Total with taxes and fees
CRISTY'S CABIN - cozy and quaint - where the deer and the ants play!
A hot tub in a wooden cabin with a view of the forest.

17. 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, (136 reviews)
"The cabin was as comfortable as it was charming. We’d love to stay again in the Fall."
United States
Nancy D.
$313 nightly
The price is $345
Nov 16 - Nov 17
Total with taxes and fees
Private Cottage at Lake Cumberland Resort- a gated lakefront Community
A wooden interior with a wooden door, a wreath, a small table, and a vase of flowers.

18. Avery Acres

Avery Acres
Albany
9.6 out of 10, Exceptional, (7 reviews)
"Perfect location, very nice home,"
United States
Josh W.
$205 nightly
The price is $226
Nov 16 - Nov 17
Total with taxes and fees
Avery Acres
A hot tub with a view of a forested area.

19. Cozy 2-Bedroom Cabin Overlooking Beautiful Lake Cumberland

Cozy 2-Bedroom Cabin Overlooking Beautiful Lake Cumberland
Nancy
9.6 out of 10, Exceptional, (8 reviews)
"Very nice place "
United States
kashyap p.
$228 nightly
The price is $251
Nov 17 - Nov 18
Total with taxes and fees
Cozy 2-Bedroom Cabin Overlooking Beautiful Lake Cumberland
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

Cozy, private, 1-bedroom cabin in Monroe, near Livingston, Dale Hollow Lake
Monroe
10.0 out of 10, Exceptional, (4 reviews)
"Cabin was everything that says it is. Would stay again"
United States
Anonymous traveler
$92 nightly
The price is $103
Nov 29 - Nov 30
Total with taxes and fees
Cozy, private, 1-bedroom cabin in Monroe, near Livingston, Dale Hollow Lake
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

Quality Inn & Suites Somerset

Quality Inn & Suites Somerset

8/10 Good
"Overall my stay was pleasant. Front desk staff member Lisa was very polite and helpful. She went out of her way to make me feel welcome. She is a great asset to Quality Inn. It was calm and quiet at night. Thank you."
Robin 2-night trip
Posted less than an hour ago
Quality Inn & Suites Somerset

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.