Monticello Holiday Rentals

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Holiday Rentals in Monticello

Cottage in Monticello

10.0 out of 10, Exceptional, (3)
"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 AU$420
includes taxes & fees
12 Dec - 13 Dec
Serene Cottage on 18 Acres Close to Lake Cumberland

Holiday Home in Monticello

9.8 out of 10, Exceptional, (51)
"The cottage is adorable. It is clean and well kept. It has everything you need. We only stayed two nights but it perfect for a longer stay. We enjoyed our stay completely. "
United States
Kim H.
The price is AU$291
includes taxes & fees
13 Dec - 14 Dec
The Cozy Cabell Cottage

Holiday Home in Monticello

10.0 out of 10, Exceptional, (31)
"This was a great house! Super clean, spacious and had everything we needed. We enjoyed the hot tub, firepit, and the grill. It was 30 mins to Conley Bottom marina and 15 mins to a grocery store. We would stay here again next time we're back!!"
United States
Elizabeth B.
The price is AU$775
includes taxes & fees
10 Dec - 11 Dec
Luxe Lake Barndo w/ 2 King Suites! Hot Tub, Fire Pit, 1/8 mile to boat ramp!

Mobile Home in Jamestown

10.0 out of 10, Exceptional, (3)
"We had the best stay.. will definitely try to just them again next year for our family reunion "
United States
Lisa B.
The price is AU$285
includes taxes & fees
15 Dec - 16 Dec
Cozy 2-bedroom, 1.5 bath RV with outdoor kitchen, 3.5 miles from Wolf Creek Dam

Mobile Home in Burkesville

2.0 star property
The price is AU$292
includes taxes & fees
10 Dec - 11 Dec
~Lady May~Glamping on DaleHollow<4 miles lake/golf

Camping in Jamestown

3.0 star property
10.0 out of 10, Exceptional, (3)
"So novel and fun!"
United States
Sharon
The price is AU$311
includes taxes & fees
17 Dec - 18 Dec
Glamping Back in Time

Cabin in Nancy

9.4 out of 10, Exceptional, (37)
"Great place for cheap!"
United States
Jamie M.
The price is AU$255
includes taxes & fees
11 Dec - 12 Dec
Timy Home near Wolf Creek Marina & multiple boat ramps with a full kitchen

Cabin in Alpine

10.0 out of 10, Exceptional, (1)
The price is AU$301
includes taxes & fees
18 Dec - 19 Dec
Lazy Lake Days • Fast Wifi • Roku TV • Free Firewood

Cabin in Albany

10.0 out of 10, Exceptional, (15)
"Perfect getaway near Lake Cumberland"
United States
ANDREW G.
The price is AU$318
includes taxes & fees
10 Dec - 11 Dec
Newly renovated near Rowena, Grider and Wolf Creek Dam

Cabin in Allardt

9.8 out of 10, Exceptional, (31)
"It was a perfect setting for the two of us to get away and relax! Beautiful neighborhood as well. "
United States
Barb G.
The price is AU$309
includes taxes & fees
21 Dec - 22 Dec
Romantic Cabarn w/ HotTub Lounge - Located on BSF!

Holiday Home in Burkesville

10.0 out of 10, Exceptional, (87)
"It’s so nice and clean and convenient that we will be back! "
United States
Kim M.
The price is AU$251
includes taxes & fees
10 Dec - 11 Dec
Boating Mecca: Near Dale Hollow Lake & Golf!

Cabin in Alpine

10.0 out of 10, Exceptional, (5)
"Perfect mix of comfort and rustic"
United States
Sadie P.
The price is AU$301
includes taxes & fees
18 Dec - 19 Dec
The Boathouse Bungalow • Dale Hollow Lake 1 Minute Away • Free Firewood • Pet-Friendly •

Cabin in Allardt

9.8 out of 10, Exceptional, (9)
"Really enjoyed the stay and will likely be back."
United States
Mike W.
The price is AU$240
includes taxes & fees
10 Dec - 11 Dec
The Honey Hut next to Big South Fork NRRA with AC, wifi, and horse stalls.

Holiday Home in Faubush

10.0 out of 10, Exceptional, (3)
"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 AU$292
includes taxes & fees
15 Dec - 16 Dec
LAKE CUMBERLAND Get-a-Way! Charming House. BOAT RAMP NEARBY - Wifi - RV Hookups

Cabin in Jamestown

2.0 star property
9.4 out of 10, Exceptional, (13)
"Such a lovely property. Very cozy and inviting. We will definitely stay again."
United States
Jennifer S.
The price is AU$540
includes taxes & fees
15 Dec - 16 Dec
NEW HOT TUB Cozy Cabin Cumberland River near Lake Cumberland~Firepit~New build

Apartment in Jamestown

8.8 out of 10, Excellent, (5)
"Great location."
United States
Donald S.
The price is AU$209
includes taxes & fees
14 Dec - 15 Dec
Studio Cottage on the Square, entire rental unit in Jamestown, Kentucky

Cottage in Burnside

10.0 out of 10, Exceptional, (1)
"Stayed here 2 nights in order to visit Cumberland Falls which was only 30 minutes away. We had a very warm welcome and comfortable stay. Would definitely stay here again. "
United States
Christina N.
The price is AU$229
includes taxes & fees
10 Dec - 11 Dec
Luxury Linens and Towels, King Size Bed hybrid medium pillow top mattress

Holiday Home in Somerset

2.0 star property
9.6 out of 10, Exceptional, (4)
"House is super cute. Great location for the weekend car activities."
United States
Penny H.
The price is AU$243
includes taxes & fees
10 Dec - 11 Dec
Cozy 1-bedroom Tiny House with WiFi, AC in beautiful Somerset

Cabin in Oneida

9.6 out of 10, Exceptional, (13)
"Clean, well kept and comfortable."
United States
Richard M.
The price is AU$308
includes taxes & fees
10 Dec - 11 Dec
Cabin #1 Cozy and relaxing cabin near Big South Fork

Cottage in Somerset

9.8 out of 10, Exceptional, (153)
"It was a great stay we had a great time enjoying the water and the area around ! Thank you and until next time!"
United States
RJ S.
The price is AU$347
includes taxes & fees
14 Dec - 15 Dec
Serene Lakefront Retreat: Close to Marina, Park, & Downtown Charm
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

Everything you need to know about Monticello holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Monticello holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Monticello holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Monticello holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Monticello holiday rentals we have selected for you start as low as AU$611 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Monticello rentals

At Expedia, we put the best Monticello holiday 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 holiday.

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. 

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?

Large 8 Bedroom Home Overlooking Play Area, And Pool. Great For Family Reunions.: This highly rated holiday home rental in Monticello is located in a rural location, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Other favourite homes for rent in Monticello are 6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more😍 and 4 Bedrooms, Heated Private pool, hot tub, Game room, and Water Front View!.

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, Lake Cumberland Winery and Conley Bottom Marina 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.