A winding fence on a grassy hill with horses grazing.

Monticello Holiday Rentals

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Our top choices for Monticello holiday rentals

1. 3 BDR HOUSE-HOT/TUB-POOL TABLE-GRILL-FIRE PIT-WIFII-SELF CHECKIN-COVERED PORCH

3 BDR HOUSE-HOT/TUB-POOL TABLE-GRILL-FIRE PIT-WIFII-SELF CHECKIN-COVERED PORCH
Monticello
10.0 out of 10, Exceptional, (1 review)
"This place is nice looks newly renovated and was very clean the host communicated very well with us"
United States
Justin M.
The price is NZ$423
includes taxes & fees
22 Aug - 23 Aug
3 BDR HOUSE-HOT/TUB-POOL TABLE-GRILL-FIRE PIT-WIFII-SELF CHECKIN-COVERED PORCH

2. 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 NZ$321
includes taxes & fees
16 Aug - 17 Aug
The Cozy Cabell Cottage

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 NZ$453
includes taxes & fees
16 Aug - 17 Aug
Lakeside Escape - Charming home centrally located on Lake Cumberland

4. 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.
The price is NZ$939
includes taxes & fees
15 Sept - 16 Sept
Lake Access ~ King Ensuites w/ fireplaces~ Hot Tub~ Fire Pit~ Boat Ramp

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)
"Great place for cheap!"
United States
Jamie M.
The price is NZ$312
includes taxes & fees
17 Aug - 18 Aug
Timy Home near Wolf Creek Marina & multiple boat ramps with a full kitchen

6. 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 NZ$335
includes taxes & fees
15 Sept - 16 Sept
CRISTY'S CABIN - cozy and quaint - where the deer and the ants play!

7. 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
The price is NZ$348
includes taxes & fees
16 Aug - 17 Aug
New Near Jamestown Dock - A

8. Lake Cumberland "Idol Time Cabin" near Clearwater

Lake Cumberland "Idol Time Cabin" near Clearwater
Nancy
9.4 out of 10, Exceptional, (9 reviews)
"Clean, quiet and safe."
United States
Robin M.
The price is NZ$369
includes taxes & fees
16 Aug - 17 Aug
Lake Cumberland "Idol Time Cabin" near Clearwater

9. White Oak Cottage - Resort Pool, Boat Slip

White Oak Cottage - Resort Pool, Boat Slip
Burnside
10.0 out of 10, Exceptional, (9 reviews)
"This place is a beautiful new build that has everything you will ever need for any length of stay. Highly recommended for anyone visiting the area. We really liked the location, and the fact that all our entertainment was very close. "
United States
steve S.
The price is NZ$833
includes taxes & fees
14 Sept - 15 Sept
White Oak Cottage - Resort Pool, Boat Slip

10. 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 NZ$650
includes taxes & fees
16 Aug - 17 Aug
Lake Cabin, Fishing Access, swimming, walk to lake, boat parking, fenced yard!

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 NZ$454
includes taxes & fees
17 Aug - 18 Aug
LAKE CUMBERLAND Get-a-Way! Charming House. BOAT RAMP NEARBY - Wifi - RV Hookups

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 NZ$481
includes taxes & fees
17 Aug - 18 Aug
Lake Cumberland Cabin

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

Lake Daze, Blue Cottage <1mile to Jamestown Marina with space to trailer boat.
Jamestown
9.4 out of 10, Exceptional, (31 reviews)
"Great location, very comfortable, and pet friendly. We had friends at the campground behind the house, so it was great to walk over on the path in the back yard. We also checked out the state park and Lily Creek falls. Beautiful area!"
United States
Emily W.
The price is NZ$687
includes taxes & fees
16 Aug - 17 Aug
Lake Daze, Blue Cottage <1mile to Jamestown Marina with space to trailer boat.

14. Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!

Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!
Jamestown
9.8 out of 10, Exceptional, (29 reviews)
"Excellent place to stay."
United States
Jason E.
The price is NZ$939
includes taxes & fees
17 Aug - 18 Aug
Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!

15. Restful Rustic Farmhouse on Lake Cumberland

Restful Rustic Farmhouse on Lake Cumberland
Jamestown
9.4 out of 10, Exceptional, (15 reviews)
"Our family had an amazing time at this vacation home! We had excellent communication with the owners and the place had everything we needed! Will definitely stay here again! Thank you for a wonderful holiday weekend!"
United States
Dana C.
The price is NZ$1,278
includes taxes & fees
17 Aug - 18 Aug
Restful Rustic Farmhouse on Lake Cumberland

16. Lake Cumberland Cabin Getaway! Quick Local Lake Access!

Lake Cumberland Cabin Getaway! Quick Local Lake Access!
Russell Springs
10.0 out of 10, Exceptional, (12 reviews)
"Great wooded cabins stay near lake Cumberland"
United States
Emily N.
The price is NZ$690
includes taxes & fees
17 Aug - 18 Aug
Lake Cumberland Cabin Getaway! Quick Local Lake Access!

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

Country Comfort on Lake Cumberland!! 5 miles from Marina Rowena; Lake Cumberland
Albany
10.0 out of 10, Exceptional, (2 reviews)
"Great place to stay. Easy access to lake. Was everything we hoped it would be."
United States
Eric G.
The price is NZ$547
includes taxes & fees
17 Aug - 18 Aug
Country Comfort on Lake Cumberland!! 5 miles from Marina Rowena; Lake Cumberland

18. 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.
The price is NZ$364
includes taxes & fees
16 Aug - 17 Aug
Cozy Cabin

19. 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 NZ$335
includes taxes & fees
16 Aug - 17 Aug
Studio Cottage on the Square, entire rental unit in Jamestown, Kentucky

20. 5-bedroom vacation home with private slip, just 10 minutes from the marina

5-bedroom vacation home with private slip, just 10 minutes from the marina
Somerset
9.6 out of 10, Exceptional, (34 reviews)
"This was perfect for my son's wedding weekend. Plenty of room, wonderful view, & very clean."
United States
Melissa W.
The price is NZ$1,805
includes taxes & fees
17 Aug - 18 Aug
5-bedroom vacation home with private slip, just 10 minutes from the marina
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

Find out more about Monticello

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

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

Frequently asked questions

Can I find a holiday rental in Monticello?

Yes, there are holiday rentals close to the most popular sights in Monticello, or you can select a more 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 holiday rentals that Monticello has to offer?

6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more: This highly rated holiday home rental in Monticello offers an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. Other favourite 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 holiday rentals are there in Monticello?

With 43 Expedia holiday rentals, you're guaranteed 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 holiday rental in Monticello like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Monticello. Holiday rentals feature extras like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy front desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for family trips.