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
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Monticello vacation rentals

TV, books

1. The Cozy Cabell Cottage

The Cozy Cabell Cottage
Monticello
9.8 out of 10, Exceptional, (56 reviews)
"This was the perfect place to stay for our weekend fishing trip, everything was very clean and overall a great experience."
United States
Austin S.
The price is CA $107
CA $265 total
includes taxes & fees
Aug 19 - Aug 20
The Cozy Cabell Cottage
Property grounds

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, (38 reviews)
"Had such an amazing time in this beautiful home. Will definitely be back!"
United States
Monika H.
The price is CA $314
CA $835 total
includes taxes & fees
Sep 2 - Sep 3
Lake Access ~ King Ensuites w/ fireplaces~ Hot Tub~ Fire Pit~ Boat Ramp
Coffee/tea maker, fridge, microwave, oven

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.
The price is CA $300
CA $379 total
includes taxes & fees
Aug 10 - Aug 11
Lakeside Escape - Charming home centrally located on Lake Cumberland
Interior

4. 6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more

6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more
Monticello
9.8 out of 10, Exceptional, (46 reviews)
"Clean,warm atmosphere, parking was easy with multiple vehicles. The pool was awesome "
United States
Kimberly K.
The price is CA $631
CA $1,148 total
includes taxes & fees
Aug 10 - Aug 11
6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more
Interior

5. 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)
"This is a basic very small cabin along a winding country road. There are outdoor chairs to sit in, but no view other than the road and neighbors--so use this as a tiny place to stay if you want to read or watch TV, or to visit the marina 4 miles farther down the road."
United States
Norman
The price is CA $65
CA $257 total
includes taxes & fees
Aug 18 - Aug 19
Timy Home near Wolf Creek Marina & multiple boat ramps with a full kitchen
Smart TV

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
The price is CA $175
CA $304 total
includes taxes & fees
Aug 8 - Aug 9
Lake Cumberland "Lake Daze Cabin" near Clearwater
Microwave, oven, stovetop, paper towels

7. 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, (26 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.
The price is CA $114
CA $283 total
includes taxes & fees
Aug 12 - Aug 13
Newly renovated near Rowena, Grider and Wolf Creek Dam
Exterior

8. 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
The price is CA $175
CA $281 total
includes taxes & fees
Sep 3 - Sep 4
CRISTY'S CABIN - cozy and quaint - where the deer and the ants play!
Dining

9. New Near Jamestown Dock - A

New Near Jamestown Dock - A
Jamestown
9.6 out of 10, Exceptional, (26 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
The price is CA $126
CA $287 total
includes taxes & fees
Aug 9 - Aug 10
New Near Jamestown Dock - A
Terrace/patio

10. Cozy Cabin

Cozy Cabin
Burnside
9.2 out of 10, Wonderful, (13 reviews)
"It was an amazing stay very clean close to the river very relaxing"
United States
Jeremy C.
The price is CA $158
CA $304 total
includes taxes & fees
Aug 12 - Aug 13
Cozy Cabin
2 bedrooms, iron/ironing board, WiFi (free), bed sheets

11. 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, (6 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 $147
CA $380 total
includes taxes & fees
Aug 10 - Aug 11
LAKE CUMBERLAND Get-a-Way! Charming House. BOAT RAMP NEARBY - Wifi - RV Hookups
Outdoor dining

12. Lake Cumberland Cabin

Lake Cumberland Cabin
Bronston
9.8 out of 10, Exceptional, (17 reviews)
"No complaints for this stay"
United States
Trisha E.
The price is CA $185
CA $399 total
includes taxes & fees
Aug 8 - Aug 9
Lake Cumberland Cabin
Terrace/patio

13. Peaceful Russell Springs Home w/ Fire Pit & Pond!

Peaceful Russell Springs Home w/ Fire Pit & Pond!
Russell Springs
9.6 out of 10, Exceptional, (7 reviews)
"Very nice clean comfortable place and setting. "
United States
Delmar B.
The price is CA $116
CA $392 total
includes taxes & fees
Aug 8 - Aug 9
Peaceful Russell Springs Home w/ Fire Pit & Pond!
2 bedrooms, WiFi (free)

14. 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.
The price is CA $156
CA $281 total
includes taxes & fees
Aug 9 - Aug 10
Studio Cottage on the Square, entire rental unit in Jamestown, Kentucky
Terrace/patio

15. 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.
The price is CA $158
CA $205 total
includes taxes & fees
Aug 9 - Aug 10
Charming 1-bedroom fish shack in Somerset with WiFi and AC
Outdoor spa tub

16. Cozy 2-Bedroom Cabin Overlooking Beautiful Lake Cumberland

Cozy 2-Bedroom Cabin Overlooking Beautiful Lake Cumberland
Nancy
10.0 out of 10, Exceptional, (3 reviews)
"Very nice place "
United States
kashyap p.
The price is CA $224
CA $371 total
includes taxes & fees
Aug 10 - Aug 11
Cozy 2-Bedroom Cabin Overlooking Beautiful Lake Cumberland
Coffee/tea maker, fridge, microwave, oven

17. 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.
The price is CA $221
CA $537 total
includes taxes & fees
Aug 9 - Aug 10
Lake Cabin, Fishing Access, swimming, walk to lake, boat parking, fenced yard!
Smart TV, fireplace

18. Hot Tub~Firepit~Riverfront~Near Lake Cumberland

Hot Tub~Firepit~Riverfront~Near Lake Cumberland
Jamestown
10.0 out of 10, Exceptional, (3 reviews)
"Very clean and quiet. The beds were comfortable and the house was stocked with nice touches like laundry pods and coffee. I would definitely stay there again!"
United States
Christine V.
The price is CA $159
CA $508 total
includes taxes & fees
Aug 10 - Aug 11
Hot Tub~Firepit~Riverfront~Near Lake Cumberland
Smart TV, fireplace

19. 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, (18 reviews)
"Such a lovely property. Very cozy and inviting. We will definitely stay again."
United States
Jennifer S.
The price is CA $144
CA $485 total
includes taxes & fees
Aug 18 - Aug 19
NEW HOT TUB Cozy Cabin Cumberland River near Lake Cumberland~Firepit~New build
Smart TV

20. Eagles Nest Lake Retreat

Eagles Nest Lake Retreat
Russell Springs
10.0 out of 10, Exceptional, (1 review)
"I'm no wordsmith but this place was nice and well put together. The host was very nice and the place was exactly what I needed"
United States
C W.
The price is CA $126
CA $288 total
includes taxes & fees
Aug 31 - Sep 1
Eagles Nest Lake Retreat
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

Holiday Inn Express & Suites Somerset Central by IHG

Holiday Inn Express & Suites Somerset Central by IHG

10/10 Excellent
"Very nice and clean. Love that they provided parking in the back for a truck and trailer. Nice overnight stay."
Elizabeth 1-night trip
Posted 6 hours ago
Holiday Inn Express & Suites Somerset Central by IHG

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 Sunshine Escape: Spacious 6BR Home w/ Outdoor Oasis & Fire Pit, Near Marina.

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, 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.