Photo by Lisa Klein

Monticello Holiday Rentals

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Check prices for these dates

Tonight
17 Feb - 18 Feb
Tomorrow
18 Feb - 19 Feb
This weekend
21 Feb - 23 Feb
Next weekend
28 Feb - 2 Mar

Holiday Rentals in Monticello

Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!
Outdoor spa tub

Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!

10.0 out of 10, Exceptional, (104)
"We enjoyed sitting on the screened-in patio overlooking the river watching the falling leaves float to the ground. Watched a group of 15 wild turkeys make the way way past the property. their wwa"
Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!
6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍
Interior

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

9.8 out of 10, Exceptional, (20)
"My family of nine and I had a great time and plenty of room. The views are incredible. The toys including pool table and foosball were used heavily. The hot tub was very comfortable and easy to use. There were a couple of unexpected bonuses including an extra refrigerator in the garage which was very helpful for all the food we needed for Thanksgiving, and secondly that they had two sets of washers and dryers which was very helpful for a large group. The second flat parking pad beyond the pool...
6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍
Cumberland Belle Lakehouse 9 bedrm, 20 bed, 7 bath, swimspa/hotub&sauna
Miscellaneous

Cumberland Belle Lakehouse 9 bedrm, 20 bed, 7 bath, swimspa/hotub&sauna

9.6 out of 10, Exceptional, (5)
"We all had a great time celebrating our Mom, (Grandma, Great Grandma's) 92 Birthday. Kids had a great time playing all the fun "toys" available on the 1st Floor- overall a really great time. "
Cumberland Belle Lakehouse 9 bedrm, 20 bed, 7 bath, swimspa/hotub&sauna
Cozy Cabin - Lake Cumberland - Hot Tub
Terrace/patio

Cozy Cabin - Lake Cumberland - Hot Tub

9.6 out of 10, Exceptional, (20)
"This little cabin was exactly what my partner and I needed to get away from the city for a quick weekend during the winter. It feels private without being too far from a scenic walk or a trip to the store, in case you forgot anything. The host was incredible and the cozy cabin is aptly named. Would stay again!"
Cozy Cabin - Lake Cumberland - Hot Tub
Lake house with boat ramp access across the street & tons of boat parking space.
Interior

Lake house with boat ramp access across the street & tons of boat parking space.

9.8 out of 10, Exceptional, (67)
"Our third year at this location for our family and friends get together. Great location. Perfect for our event! Thanks to the host for all the preparations. Highly satisfied and will very likely use the same property again next year. "
Lake house with boat ramp access across the street & tons of boat parking space.
Luxe Lake Barndo w/ 2 King Suites! Hot Tub, Fire Pit, 1/8 mile to boat ramp!
Outdoor spa tub

Luxe Lake Barndo w/ 2 King Suites! Hot Tub, Fire Pit, 1/8 mile to boat ramp!

10.0 out of 10, Exceptional, (17)
"The home is absolutely stunning and the pictures do not do it justice! Own"
The price is AU$610
includes taxes & fees
18 Feb - 19 Feb
Luxe Lake Barndo w/ 2 King Suites! Hot Tub, Fire Pit, 1/8 mile to boat ramp!
Lake Cumberland Home 1/2 Mi to Beaver Creek Marina
Outdoor dining

Lake Cumberland Home 1/2 Mi to Beaver Creek Marina

9.2 out of 10, Wonderful, (62)
"Great time. Peaceful setting. "
Lake Cumberland Home 1/2 Mi to Beaver Creek Marina
This charming cozy cottage has a private hot tub, deck for fishing.
Property grounds

This charming cozy cottage has a private hot tub, deck for fishing.

9.8 out of 10, Exceptional, (145)
"We would like to stay there again because of all the amenities the manager was very friendly"
This charming cozy cottage has a private hot tub, deck for fishing.
Spacious House on the Water - Lake Cumberland
Fridge, microwave, oven, stovetop

Spacious House on the Water - Lake Cumberland

10.0 out of 10, Exceptional, (40)
"My friends and I rented the cabin for a weekend of board gaming and catching up. The kitchen was put to great use and we appreciated the open space, variety of cookware and utensils. The fire pit was the perfect place to watch the Geminid meteor shower, too! "
Spacious House on the Water - Lake Cumberland
COUNTRY PEACEFUL, FENCED YARD, FIRE PIT, HOT TUB, 100 meg internet, FIREPLACE
Outdoor spa tub

COUNTRY PEACEFUL, FENCED YARD, FIRE PIT, HOT TUB, 100 meg internet, FIREPLACE

10.0 out of 10, Exceptional, (231)
"My wife and I stayed at this house with our dog over New Year’s Eve. It was so cozy, relaxing, and the perfect getaway for our family. The hot tub was great and we loved hiking at the Boone National Forest which was only about 20 minutes from the house. We will definitely be coming back in the future. "
COUNTRY PEACEFUL, FENCED YARD, FIRE PIT, HOT TUB, 100 meg internet, FIREPLACE
LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY
Outdoor dining

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

10.0 out of 10, Exceptional, (127)
"A winter storm was approaching at the start of our stay, and the host was extremely accommodating with us allowing us to arrive early. The views from the home as the snow fell were breathtaking. The house is conveniently located in a quiet area but close to town. The roads were icy one day when we were returning to the house, but we made it back without any issues. There is one hill near the house I was worried about, but we didn't have any issues. Our group loved playing games and spending time...
LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY
Lake Front Home with community boat ramp. Private, close to marinas and town.
Interior

Lake Front Home with community boat ramp. Private, close to marinas and town.

9.6 out of 10, Exceptional, (214)
"We enjoyed our stay at this cute cabin with a great view located close to town. The hosts were excellent at communication and responded quickly. The deck is the focal point and is great for sitting out and admiring the water, enjoying an evening fire or cooking out dinner. My only complaint is in sleeping comfort. The bed in the main bedroom was so hard the first night that we switched to the other bedroom the second night. In that room, the bed was much better, but the window blind is too small...
Lake Front Home with community boat ramp. Private, close to marinas and town.
JAMESTOWN Marina, LCKY. boat parking. pool table. 3 full baths. pet friendly.
Property grounds

JAMESTOWN Marina, LCKY. boat parking. pool table. 3 full baths. pet friendly.

10.0 out of 10, Exceptional, (161)
"Wonderful stay!!! House was adorable and as described. The house was very clean and well stocked. Loved the ability to regulate the temperature for each room with the mini split units throughout. Suzanne was excellent host and very detailed in her communication. Thank You for a great stay!"
JAMESTOWN Marina, LCKY. boat parking. pool table. 3 full baths. pet friendly.
5-bedroom vacation home near Daniel Boone National Forest

5-bedroom vacation home near Daniel Boone National Forest

10.0 out of 10, Exceptional, (102)
"My family gathered for Christmas in KY this year. Our host Dave was amazing. We had everything we needed to celebrate. The house was decorated and the kitchen had every imaginable necessity to cook some big meals. To say the kitchen was well stocked is an understatement. Dave was personable and attentive and had great suggestions for dinner and Christmas Eve service. If we travel in the area again and need a big house for all of us we all agree we would stay there again. The surrounding area was...
5-bedroom vacation home near Daniel Boone National Forest
NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking
Miscellaneous

NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking

10.0 out of 10, Exceptional, (33)
"I can’t stress enough how BEAUTIFUL the view is from both inside(huge windows) and outside(2 levels of deck viewing & seating)! Wonderfully decorated, and super comfy furnishings. Definitely recommend, and will be back! "
NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking
⚓ Anchor Down ⚓ Spacious lakefront home on Lake Cumberland - W/ PRIVATE SLIP!
Exterior

⚓ Anchor Down ⚓ Spacious lakefront home on Lake Cumberland - W/ PRIVATE SLIP!

9.8 out of 10, Exceptional, (17)
"Home is one of the nicest, best decorated, best kept and best stocked rentals possible! Owners have done a wonderful job and attended to the smallest details to make their guests comfortable. All the comforts of home are included in this property and owners communicate well. It is close to dock where they provide a boat slip and the experience of sitting is the ample furnishings on porch or in the living room to see one of the best lake views simply cannot be beat!"
The price is AU$1,704
includes taxes & fees
19 Feb - 20 Feb
⚓ Anchor Down ⚓ Spacious lakefront home on Lake Cumberland - W/ PRIVATE SLIP!
Prather Place, Spacious, Deck And View, Entertaining Basement, Minutes to Marina
Property grounds

Prather Place, Spacious, Deck And View, Entertaining Basement, Minutes to Marina

10.0 out of 10, Exceptional, (139)
"The house was exactly as described. Our family enjoyed the basement game room/ movie room the most. There were a couple things that would have made it better but was definitely out of the owners hands. The bridge was out so if you needed anything from Somerset, it took 30 minutes to get to instead of 5 minutes. The organization of the kitchen utensils (pots, pans, appliances, etc.) could definitely use some work. But overall, we enjoyed our stay and would recommend this place to anyone who...
Prather Place, Spacious, Deck And View, Entertaining Basement, Minutes to Marina
3BR 3BA Cabin, with hot tub, 3 Pools, Boat Ramp with Dock 1 mile away.
Interior

3BR 3BA Cabin, with hot tub, 3 Pools, Boat Ramp with Dock 1 mile away.

10.0 out of 10, Exceptional, (56)
"We rented this place for a family Christmas. It was perfect for our family to come together for a Christmas for the first time in 10 years. We are considering making this a regular thing for our family so we will definitely be considering staying again."
3BR 3BA Cabin, with hot tub, 3 Pools, Boat Ramp with Dock 1 mile away.
Lake Retreat at Lake Cumberland Resort
Indoor spa tub

Lake Retreat at Lake Cumberland Resort

9.8 out of 10, Exceptional, (166)
"We absolutely loved the property! Towels were abundant for the hot tub and bathrooms. Kitchen was stocked with everything we needed and the hot tub was great, well taken care of. We enjoyed hanging out on the two porches and it was just a short drive to eat out in Burnside. Highly recommend the owners and the property! "
Lake Retreat at Lake Cumberland Resort
Lakin’ It Easy at Lake Cumberland Resort Burnside KY 4 KING BEDS & 4 FULL BATHS
Dining

Lakin’ It Easy at Lake Cumberland Resort Burnside KY 4 KING BEDS & 4 FULL BATHS

10.0 out of 10, Exceptional, (93)
"What a beautiful property this was! We loved the ensuite bedrooms and the high end finishes in the kitchen and throughout. The arcade game in the lower level was a special treat and the view from the deck is to die for. Hopefully we'll be back!"
Lakin’ It Easy at Lake Cumberland Resort Burnside KY 4 KING BEDS & 4 FULL BATHS
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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Other types of properties in Monticello you may be interested in

Cumberland Belle Lakehouse 9 bedrm, 20 bed, 7 bath, swimspa/hotub&sauna
Miscellaneous

Cumberland Belle Lakehouse 9 bedrm, 20 bed, 7 bath, swimspa/hotub&sauna

9.6 out of 10, Exceptional, (5)
"We all had a great time celebrating our Mom, (Grandma, Great Grandma's) 92 Birthday. Kids had a great time playing all the fun "toys" available on the 1st Floor- overall a really great time. "
Cumberland Belle Lakehouse 9 bedrm, 20 bed, 7 bath, swimspa/hotub&sauna
6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍
Interior

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

9.8 out of 10, Exceptional, (20)
"My family of nine and I had a great time and plenty of room. The views are incredible. The toys including pool table and foosball were used heavily. The hot tub was very comfortable and easy to use. There were a couple of unexpected bonuses including an extra refrigerator in the garage which was very helpful for all the food we needed for Thanksgiving, and secondly that they had two sets of washers and dryers which was very helpful for a large group. The second flat parking pad beyond the pool...
6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍
Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!
Outdoor spa tub

Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!

10.0 out of 10, Exceptional, (104)
"We enjoyed sitting on the screened-in patio overlooking the river watching the falling leaves float to the ground. Watched a group of 15 wild turkeys make the way way past the property. their wwa"
Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!
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.

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, 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 Luxe Lake Barndo w/ 2 King Suites! Hot Tub, Fire Pit, 1/8 mile to boat ramp! and Cumberland Belle Lakehouse 9 bedrm, 20 bed, 7 bath, swimspa/hotub&sauna.

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?

Daniel Boone National Forest and Cumberland River 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.