Monticello Holiday Rentals

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Check prices for these dates

In two weeks
6 Feb - 8 Feb
In two months
20 Mar - 22 Mar
In three months
17 Apr - 19 Apr
In four months
15 May - 17 May

Our top choices for Monticello holiday rentals

TV, books

Holiday Home in Monticello

The Cozy Cabell Cottage
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 HK$596
HK$1,491 total
includes taxes & fees
1 Feb - 2 Feb
The Cozy Cabell Cottage
Property grounds

Cottage in Monticello

Serene Cottage on 18 Acres Close to Lake Cumberland
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 HK$1,084
HK$2,156 total
includes taxes & fees
27 Jan - 28 Jan
Serene Cottage on 18 Acres Close to Lake Cumberland
Property grounds

Holiday Home in Monticello

Luxe Lake Barndo w/ 2 King Suites! Hot Tub, Fire Pit, 1/8 mile to boat ramp!
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 HK$1,091
HK$3,529 total
includes taxes & fees
27 Jan - 28 Jan
Luxe Lake Barndo w/ 2 King Suites! Hot Tub, Fire Pit, 1/8 mile to boat ramp!
Fridge, microwave, oven, stovetop

Holiday Home in Monticello

Lakeside Escape - Charming home centrally located on Lake Cumberland
The price is HK$1,366
HK$1,678 total
includes taxes & fees
27 Jan - 28 Jan
Lakeside Escape - Charming home centrally located on Lake Cumberland
Interior

Cabin in Monticello

Between the Lakes - Hidden Creek Schoolhouse
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
Aerial view

Townhouse in Somerset

Lake It Easy 3 Level Home
2.0 star property
The price is HK$4,469
HK$4,927 total
includes taxes & fees
2 Feb - 3 Feb
Lake It Easy 3 Level Home
Exterior

Camping in Jamestown

Glamping Back in Time
10.0 out of 10, Exceptional, (3 reviews)
"So novel and fun!"
United States
Sharon
The price is HK$1,053
HK$1,584 total
includes taxes & fees
27 Jan - 28 Jan
Glamping Back in Time
Interior

Cabin in Nancy

Timy Home near Wolf Creek Marina & multiple boat ramps with a full kitchen
9.4 out of 10, Exceptional, (38 reviews)
"Great place for cheap!"
United States
Jamie M.
The price is HK$274
HK$1,334 total
includes taxes & fees
27 Jan - 28 Jan
Timy Home near Wolf Creek Marina & multiple boat ramps with a full kitchen
2 bedrooms, free WiFi

Apartment in Jamestown

Studio Cottage on the Square, entire rental unit in Jamestown, Kentucky
9.0 out of 10, Wonderful, (7 reviews)
"Great location."
United States
Donald S.
The price is HK$449
HK$1,097 total
includes taxes & fees
27 Jan - 28 Jan
Studio Cottage on the Square, entire rental unit in Jamestown, Kentucky
Interior

Holiday Home in Allardt

Cozy 1-bedroom house in charming Allardt with AC, WiFi
10.0 out of 10, Exceptional, (15 reviews)
"Great little house! Loved our stay!"
United States
shellyrhae C.
The price is HK$702
HK$959 total
includes taxes & fees
27 Jan - 28 Jan
Cozy 1-bedroom house in charming Allardt with AC, WiFi
Exterior detail

Apartment in Somerset

Pet Friendly 1 Bedroom Apartment; Quiet & Secluded - 1/2 hour from town
10.0 out of 10, Exceptional, (22 reviews)
"Nice place , great people treated us like they had known us our whole life ! "
United States
Bill D.
The price is HK$526
HK$1,397 total
includes taxes & fees
27 Jan - 28 Jan
Pet Friendly 1 Bedroom Apartment; Quiet & Secluded - 1/2 hour from town
Interior

Cabin in Allardt

Romantic Cabarn w/ HotTub Lounge - Located on BSF!
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 HK$616
HK$1,486 total
includes taxes & fees
28 Jan - 29 Jan
Romantic Cabarn w/ HotTub Lounge - Located on BSF!
Dining

Apartment in Jamestown

New Near Jamestown Dock - A
9.8 out of 10, Exceptional, (22 reviews)
"Great stay"
United States
Rob W.
The price is HK$780
HK$1,676 total
includes taxes & fees
27 Jan - 28 Jan
New Near Jamestown Dock - A
1 bedroom, iron/ironing board, free WiFi, bed sheets

Holiday Home in Somerset

Charming 1-bedroom fish shack in Somerset with WiFi and AC
10.0 out of 10, Exceptional, (10 reviews)
"The Fish Shack was awesome "
United States
Brian
The price is HK$877
HK$1,139 total
includes taxes & fees
31 Jan - 1 Feb
Charming 1-bedroom fish shack in Somerset with WiFi and AC
TV, fireplace

Cabin in oneida

cozy cabin in the woods in a relaxing area with wrap around porch rocking chairs
9.4 out of 10, Exceptional, (28 reviews)
"Quiet, clean and peaceful"
United States
Neil
The price is HK$936
HK$1,670 total
includes taxes & fees
27 Jan - 28 Jan
cozy cabin in the woods in a relaxing area with wrap around porch rocking chairs
Fridge, microwave, oven, stovetop

Holiday Home in Burkesville

Boating Mecca: Near Dale Hollow Lake & Golf!
10.0 out of 10, Exceptional, (87 reviews)
"Great place to stay. Very clean and David was quick to respond with any questions we had. Will stay again. "
United States
Doug O.
The price is HK$624
HK$1,574 total
includes taxes & fees
3 Feb - 4 Feb
Boating Mecca: Near Dale Hollow Lake & Golf!
Property grounds

Cabin in Alpine

Lazy Lake Days • Fast Wifi • Roku TV • Free Firewood
9.4 out of 10, Exceptional, (3 reviews)
"Everything was great. Easy check in. Cabin is beautiful."
United States
Michael
The price is HK$614
HK$1,521 total
includes taxes & fees
27 Jan - 28 Jan
Lazy Lake Days • Fast Wifi • Roku TV • Free Firewood
2 bedrooms, iron/ironing board, free WiFi, bed sheets

Holiday Home in Faubush

LAKE CUMBERLAND Get-a-Way! Charming House. BOAT RAMP NEARBY - Wifi - RV Hookups
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 HK$652
HK$1,578 total
includes taxes & fees
27 Jan - 28 Jan
LAKE CUMBERLAND Get-a-Way! Charming House. BOAT RAMP NEARBY - Wifi - RV Hookups
Terrace/patio

Cabin in Oneida

Cabin #1 Cozy and relaxing cabin near Big South Fork
9.6 out of 10, Exceptional, (13 reviews)
"Lovely clean cabin 15 minutes from trails. "
United States
Stephanie D.
The price is HK$936
HK$1,670 total
includes taxes & fees
27 Jan - 28 Jan
Cabin #1 Cozy and relaxing cabin near Big South Fork
Terrace/patio

Holiday Home in Helenwood

Hideaway 27
10.0 out of 10, Exceptional, (38 reviews)
"This was an absolutely beautiful and cozy stay! I definitely will stay again!"
United States
Shannon P.
The price is HK$775
HK$1,798 total
includes taxes & fees
27 Jan - 28 Jan
Hideaway 27
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

LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.

LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.

10/10 Excellent
"The location and the host is awesome. "
Soumyojyoti A. 1-night trip
Posted 5 days ago
LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.

Find out more about Monticello

Search for holiday rentals in Monticello on Expedia! You can easily find your home rentals, villas, holiday apartments in Monticello using one of the methods below:

  • View our selection of featured holiday rentals in Monticello
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Look no further and take a look at our great range of rental properties in Monticello!

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 Lake Cumberland Luxury #2! Amazing Lake views, hot tub, fire pit! 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 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, 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.