Monticello Vacation Rentals from CA $351: Short-Term Rentals for 2026

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Our top choices for Monticello vacation rentals

1. The Cozy Cabell Cottage

Monticello

tim w.

CA $264 total

includes taxes & fees

Sep 24 - Sep 25

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

Monticello

Monika H.

CA $794 total

includes taxes & fees

Sep 24 - Sep 25

Coffee/tea maker, fridge, microwave, oven

3. Lakeside Escape - Charming home centrally located on Lake Cumberland

Monticello

michelle d.

CA $374 total

includes taxes & fees

Sep 24 - Sep 25

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

Nancy

Joey A.

CA $254 total

includes taxes & fees

Sep 23 - Sep 24

2 bedrooms, iron/ironing board, WiFi (free), bed sheets

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

Faubush

Morgan P.

CA $350 total

includes taxes & fees

Sep 28 - Sep 29

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

Albany

Jasmin B.

CA $281 total

includes taxes & fees

Oct 4 - Oct 5

7. Cute and Quaint!

Albany

Randy J.

CA $258 total

includes taxes & fees

Sep 26 - Sep 27

8. New Near Jamestown Dock - A

Jamestown

Jennifer

CA $287 total

includes taxes & fees

Sep 26 - Sep 27

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Top Monticello Hotel Reviews

Dale Hollow Lake State Resort Park

10/10 Excellent

"Beautiful view, good hot showers, comfortable beds, great food, and great hospitality"

4 Bedrooms, Heated Private pool, hot tub, Game room, and Water Front View!

10/10 Excellent

"My family of six spent 3 nights at this delightful house, 4 bedrooms (2 upstairs are very large), well stocked kitchen, comfortable sectional sofa made watching a movie easy. Very much enjoyed the lake view and the pool. Did S'mores in the firepit in spite of 90 temp!! we rented a tritoon at Burnside marina and had a great day on the lake swimming and tubing. Used the grill and took advantage of the deck. Games in the basement and hot tub were enjoyed too. House is large so we had plenty of room to spread out. Clean and nice bathroom towels. Easy communication with David. Highly recommend. I hope we return. We also loved the round dining room table, Made dinners fun!!"

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

10/10 Excellent

"We had an absolutely wonderful stay! The house was beautiful, comfortable, and had the most gorgeous lakefront views. We especially loved relaxing by the fire pit and enjoying the pool. It was the perfect place to unwind and make memories. The host was incredibly communicative, helpful, and accommodating for our stay, which made everything so easy and enjoyable. We couldn’t have asked for a better experience and would absolutely love to stay here again!"

Comfort Inn Somerset - Lake Cumberland

10/10 Excellent

"Grandchildren were so excited about swimming in the pool but unfortunately it was shut down. Waiting on maintenance to fix broken door but never showed up in time that evening😒 they were so disappointed. I make sure to book a motel with indoor swimming. But overall we had a great stay!"

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 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.

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Check prices for these dates

Our top choices for Monticello vacation rentals

1. The Cozy Cabell Cottage

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

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

7. Cute and Quaint!

8. New Near Jamestown Dock - A

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

10. Cozy, private, 1-bedroom cabin in Monroe, near Livingston, Dale Hollow Lake

11. Cozy 2-Bedroom Cabin Overlooking Beautiful Lake Cumberland

12. Lake Cumberland "Idol Time Cabin" near Clearwater

13. Cozy Lake Cumberland Lakeview Shangri-la

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

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

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

17. Woodson Bend, Condo 7-3 Extremely Large, with 1 Bedroom & 1 Full Bath, Sleeps 6

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

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

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

Find vacation rentals that suit your style

Top Monticello Hotel Reviews

Dale Hollow Lake State Resort Park

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

4 Bedrooms, Heated Private pool, hot tub, Game room, and Water Front View!

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

Comfort Inn Somerset - Lake Cumberland

Red Roof Inn Somerset, KY

Holiday Inn Express & Suites Somerset Central by IHG

Courtyard by Marriott Somerset

7 Gables Motel Burnside Near Somerset US 27

Find out more about Monticello

Frequently asked questions

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