Monticello Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Monticello vacation rentals

Serene Cottage on 18 Acres Close to Lake Cumberland

Serene Cottage on 18 Acres Close to Lake Cumberland
Monticello
10.0 out of 10, Exceptional, (3 reviews)
"Our whole stay was effortless! From communication with Jamie, property location, access and matching expectations as advertised. What a delight to, for once, not be unpleasantly surprised by VRBO. We will definitely consider this place in the future. "
United States
Kenneth C.
The price is CA $190
CA $377 total
includes taxes & fees
Feb 8 - Feb 9
Serene Cottage on 18 Acres Close to Lake Cumberland

The Cozy Cabell Cottage

The Cozy Cabell Cottage
Monticello
9.8 out of 10, Exceptional, (52 reviews)
"Very clean and cozy. Saw deer off the of the back porch."
United States
Matthew S.
The price is CA $105
CA $259 total
includes taxes & fees
Feb 8 - Feb 9
The Cozy Cabell Cottage

Luxe Lake Barndo w/ 2 King Suites! Hot Tub, Fire Pit, 1/8 mile to boat ramp!

Luxe Lake Barndo w/ 2 King Suites! Hot Tub, Fire Pit, 1/8 mile to boat ramp!
Monticello
10.0 out of 10, Exceptional, (32 reviews)
"This beautiful home is made for a wonderful family getaway. My family had an amazing time relaxing and reconnecting in this well-appointed retrear. Stephanie, the host, was very comminicative throughout our stay. "
United States
Joshua H.
The price is CA $170
CA $586 total
includes taxes & fees
Feb 8 - Feb 9
Luxe Lake Barndo w/ 2 King Suites! Hot Tub, Fire Pit, 1/8 mile to boat ramp!

Lakeside Escape - Charming home centrally located on Lake Cumberland

Lakeside Escape - Charming home centrally located on Lake Cumberland
Monticello
The price is CA $240
CA $299 total
includes taxes & fees
Feb 8 - Feb 9
Lakeside Escape - Charming home centrally located on Lake Cumberland

Between the Lakes - Hidden Creek Schoolhouse

Between the Lakes - Hidden Creek Schoolhouse
Monticello
10.0 out of 10, Exceptional, (3 reviews)
"The space was so comfortable and cozy. Very quiet, great internet, responsive hosts. "
United States
Blair R.
Between the Lakes - Hidden Creek Schoolhouse

Glamping Back in Time

Glamping Back in Time
Jamestown
10.0 out of 10, Exceptional, (3 reviews)
"So novel and fun!"
United States
Sharon
The price is CA $185
CA $279 total
includes taxes & fees
Feb 8 - Feb 9
Glamping Back in Time

Newly renovated near Rowena, Grider and Wolf Creek Dam

Newly renovated near Rowena, Grider and Wolf Creek Dam
Albany
10.0 out of 10, Exceptional, (15 reviews)
"Perfect getaway near Lake Cumberland"
United States
ANDREW G.
The price is CA $123
CA $291 total
includes taxes & fees
Feb 8 - Feb 9
Newly renovated near Rowena, Grider and Wolf Creek Dam

The Honey Hut next to Big South Fork NRRA with AC, wifi, and horse stalls.

The Honey Hut next to Big South Fork NRRA with AC, wifi, and horse stalls.
Allardt
9.8 out of 10, Exceptional, (12 reviews)
"Really enjoyed the stay and will likely be back."
United States
Mike W.
The price is CA $117
CA $200 total
includes taxes & fees
Feb 11 - Feb 12
The Honey Hut next to Big South Fork NRRA with AC, wifi, and horse stalls.

Cozy 1-bedroom house in charming Allardt with AC, WiFi

Cozy 1-bedroom house in charming Allardt with AC, WiFi
Allardt
10.0 out of 10, Exceptional, (15 reviews)
"Great little house! Loved our stay!"
United States
shellyrhae C.
The price is CA $123
CA $168 total
includes taxes & fees
Feb 15 - Feb 16
Cozy 1-bedroom house in charming Allardt with AC, WiFi

Lazy Lake Days • Fast Wifi • Roku TV • Free Firewood

Lazy Lake Days • Fast Wifi • Roku TV • Free Firewood
Alpine
9.4 out of 10, Exceptional, (3 reviews)
"Everything was great. Easy check in. Cabin is beautiful."
United States
Michael
The price is CA $108
CA $265 total
includes taxes & fees
Feb 8 - Feb 9
Lazy Lake Days • Fast Wifi • Roku TV • Free Firewood

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

Charming 1-bedroom fish shack in Somerset with WiFi and AC
Somerset
10.0 out of 10, Exceptional, (10 reviews)
"The Fish Shack was awesome "
United States
Brian
The price is CA $154
CA $200 total
includes taxes & fees
Feb 13 - Feb 14
Charming 1-bedroom fish shack in Somerset with WiFi and AC

Cabin #4 Secluded and Quiet

Cabin #4 Secluded and Quiet
Oneida
10.0 out of 10, Exceptional, (3 reviews)
"The cabin was BEAUTIFUL, clean and had the most amazing view. "
United States
LeeAnn B.
The price is CA $157
CA $288 total
includes taxes & fees
Feb 8 - Feb 9
Cabin #4 Secluded and Quiet

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, (38 reviews)
"Great place for cheap!"
United States
Jamie M.
The price is CA $48
CA $234 total
includes taxes & fees
Feb 8 - Feb 9
Timy Home near Wolf Creek Marina & multiple boat ramps with a full kitchen

Romantic Cabarn w/ HotTub Lounge - Located on BSF!

Romantic Cabarn w/ HotTub Lounge - Located on BSF!
Allardt
9.8 out of 10, Exceptional, (32 reviews)
"The cabarn and hot tub lounge were both very clean. It’s a beautiful place to stay. "
United States
Jamie V.
The price is CA $116
CA $271 total
includes taxes & fees
Feb 16 - Feb 17
Romantic Cabarn w/ HotTub Lounge - Located on BSF!

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, (18 reviews)
"It was a great home on a quiet street. Nice new home was very quaint. "
United States
Dana L.
The price is CA $170
CA $217 total
includes taxes & fees
Feb 10 - Feb 11
Cordial chalet with a balcony to have coffee with the squirrels

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
10.0 out of 10, Exceptional, (3 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.
The price is CA $114
CA $278 total
includes taxes & fees
Feb 8 - Feb 9
LAKE CUMBERLAND Get-a-Way! Charming House. BOAT RAMP NEARBY - Wifi - RV Hookups

New Near Jamestown Dock - A

New Near Jamestown Dock - A
Jamestown
9.8 out of 10, Exceptional, (22 reviews)
"Great stay"
United States
Rob W.
The price is CA $137
CA $299 total
includes taxes & fees
Feb 10 - Feb 11
New Near Jamestown Dock - A

cozy cabin in the woods in a relaxing area with wrap around porch rocking chairs

cozy cabin in the woods in a relaxing area with wrap around porch rocking chairs
oneida
9.4 out of 10, Exceptional, (28 reviews)
"Quiet, clean and peaceful"
United States
Neil
The price is CA $164
CA $297 total
includes taxes & fees
Feb 8 - Feb 9
cozy cabin in the woods in a relaxing area with wrap around porch rocking chairs

Cabin #1 Cozy and relaxing cabin near Big South Fork

Cabin #1 Cozy and relaxing cabin near Big South Fork
Oneida
9.6 out of 10, Exceptional, (13 reviews)
"Lovely clean cabin 15 minutes from trails. "
United States
Stephanie D.
The price is CA $164
CA $297 total
includes taxes & fees
Feb 8 - Feb 9
Cabin #1 Cozy and relaxing cabin near Big South Fork

Cozy 2-bedroom cabin with WiFi, AC in welcoming Jamestown

Cozy 2-bedroom cabin with WiFi, AC in welcoming Jamestown
Jamestown
10.0 out of 10, Exceptional, (24 reviews)
"The host was excellent. We didn't meet her but when I texted a question, her response was very efficient. The place is gorgeous!"
United States
Julie R.
The price is CA $205
CA $437 total
includes taxes & fees
Feb 8 - Feb 9
Cozy 2-bedroom cabin with WiFi, AC in welcoming Jamestown
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Monticello Hotel Reviews

Find out more about Monticello

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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 Lake Bluff Paradise on Lake Cumberland. Game room and seasonal hot tub!.

How many vacation rentals are there in Monticello?

With 43 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 Big Island are a couple of scenic spots to enjoy the outdoors, whereas Wayne County Historical Museum is one of the cultural attractions. While here, Lake Cumberland Winery and Conley Bottom Marina 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.