Monticello Vacation Rentals

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Our top choices for Monticello vacation rentals

The Cozy Cabell Cottage

The Cozy Cabell Cottage
Monticello
9.8 out of 10, Exceptional, (52 reviews)
"Everything was very clean and well maintained. The host was very clear in what was needed when checking out. Everything was easy to find and we had no issues!"
United States
Ellie R.
The price is CA $105
CA $258 total
includes taxes & fees
May 10 - May 11
The Cozy Cabell Cottage

Modern 4BR Retreat~ King Ensuites w/ fireplaces~ Hot Tub~ Fire Pit~ Boat Ramp

Modern 4BR Retreat~ King Ensuites w/ fireplaces~ Hot Tub~ Fire Pit~ Boat Ramp
Monticello
10.0 out of 10, Exceptional, (34 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 CA $215
CA $691 total
includes taxes & fees
May 11 - May 12
Modern 4BR Retreat~ King Ensuites w/ fireplaces~ Hot Tub~ Fire Pit~ Boat Ramp

Lakeside Escape - Charming home centrally located on Lake Cumberland

Lakeside Escape - Charming home centrally located on Lake Cumberland
Monticello
The price is CA $269
CA $336 total
includes taxes & fees
May 10 - May 11
Lakeside Escape - Charming home centrally located on Lake Cumberland

Glamping Back in Time

Glamping Back in Time
Jamestown
10.0 out of 10, Exceptional, (3 reviews)
"So novel and fun!"
United States
Sharon
The price is CA $184
CA $279 total
includes taxes & fees
May 10 - May 11
Glamping Back in Time

Camper with a view - Perfect for a cozy getaway 2 Min to Lake

Camper with a view - Perfect for a cozy getaway 2 Min to Lake
Nancy
The price is CA $122
CA $179 total
includes taxes & fees
Jun 1 - Jun 2
Camper with a view - Perfect for a cozy getaway 2 Min to Lake

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, (39 reviews)
"This is a basic very small cabin along a winding country road. There are outdoor chairs to sit in, but no view other than the road and neighbors--so use this as a tiny place to stay if you want to read or watch TV, or to visit the marina 4 miles farther down the road."
United States
Norman
The price is CA $65
CA $252 total
includes taxes & fees
May 10 - May 11
Timy Home near Wolf Creek Marina & multiple boat ramps with a full kitchen

Newly renovated near Rowena, Grider and Wolf Creek Dam

Newly renovated near Rowena, Grider and Wolf Creek Dam
Albany
9.6 out of 10, Exceptional, (22 reviews)
"Perfect getaway near Lake Cumberland"
United States
ANDREW G.
The price is CA $111
CA $276 total
includes taxes & fees
May 20 - May 21
Newly renovated near Rowena, Grider and Wolf Creek Dam

Romantic Cabarn w/ HotTub Lounge - Located on BSF!

Romantic Cabarn w/ HotTub Lounge - Located on BSF!
Allardt
9.8 out of 10, Exceptional, (33 reviews)
"The outdoor seating area with tv and hot tub was amazing! "
United States
Daniel F.
The price is CA $111
CA $264 total
includes taxes & fees
May 10 - May 11
Romantic Cabarn w/ HotTub Lounge - Located on BSF!

Boating Mecca: Near Dale Hollow Lake & Golf!

Boating Mecca: Near Dale Hollow Lake & Golf!
Burkesville
10.0 out of 10, Exceptional, (93 reviews)
"super clean with everything you need for a great stay...super friendly hosts!!!"
United States
Barney H.
The price is CA $93
CA $260 total
includes taxes & fees
May 10 - May 11
Boating Mecca: Near Dale Hollow Lake & Golf!

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
10.0 out of 10, Exceptional, (5 reviews)
"Title says it all ill be staying again "
United States
Stan G.
The price is CA $146
CA $244 total
includes taxes & fees
May 11 - May 12
CRISTY'S CABIN - cozy and quaint - where the deer and the ants play!

The Honey Hut next to Big South Fork NRRA with AC, wifi, and horse stalls.

The Honey Hut next to Big South Fork NRRA with AC, wifi, and horse stalls.
Allardt
9.8 out of 10, Exceptional, (16 reviews)
"It was my second stay here. I appreciate how clean and cozy the cottage is."
United States
Ronnie B.
The price is CA $130
CA $215 total
includes taxes & fees
May 11 - May 12
The Honey Hut next to Big South Fork NRRA with AC, wifi, and horse stalls.

Cozy 1-bedroom house in charming Allardt with AC, WiFi

Cozy 1-bedroom house in charming Allardt with AC, WiFi
Allardt
10.0 out of 10, Exceptional, (16 reviews)
"The cabin is clean and cozy. A nice quiet place to stay."
United States
Diane M.
The price is CA $134
CA $181 total
includes taxes & fees
May 11 - May 12
Cozy 1-bedroom house in charming Allardt with AC, WiFi

Cozy 2-bedroom cabin with WiFi, AC in welcoming Jamestown

Cozy 2-bedroom cabin with WiFi, AC in welcoming Jamestown
Jamestown
10.0 out of 10, Exceptional, (27 reviews)
"Wonderful, quaint space perfect for our small family! "
United States
Bianca F.
The price is CA $205
CA $439 total
includes taxes & fees
May 10 - May 11
Cozy 2-bedroom cabin with WiFi, AC in welcoming Jamestown

cozy cabin in the woods in a relaxing area with wrap around porch rocking chairs

cozy cabin in the woods in a relaxing area with wrap around porch rocking chairs
oneida
9.4 out of 10, Exceptional, (28 reviews)
"Quiet, clean and peaceful"
United States
Neil
The price is CA $164
CA $297 total
includes taxes & fees
May 10 - May 11
cozy cabin in the woods in a relaxing area with wrap around porch rocking chairs

Cozy Cabin

Cozy Cabin
Burnside
9.0 out of 10, Wonderful, (12 reviews)
"It was an amazing stay very clean close to the river very relaxing"
United States
Jeremy C.
The price is CA $154
CA $295 total
includes taxes & fees
May 10 - May 11
Cozy Cabin

Whitetail Hollow- 2 bedroom 1 bath

Whitetail Hollow- 2 bedroom 1 bath
Oneida
9.2 out of 10, Wonderful, (9 reviews)
"This is not the typical Tourist cabin. It is a great place to stay to get away from everything. Very secluded but close to town if you need something. Will definitely reserve again in the future."
United States
Thomas B.
The price is CA $157
CA $288 total
includes taxes & fees
May 10 - May 11
Whitetail Hollow- 2 bedroom 1 bath

Timberwolf--Beautiful cabin near Big South Fork

Timberwolf--Beautiful cabin near Big South Fork
Oneida
10.0 out of 10, Exceptional, (15 reviews)
"Very pleasant stay at cabin. Clean, nice outdoor areas. We will stay here again."
United States
Blanca T.
The price is CA $184
CA $367 total
includes taxes & fees
May 10 - May 11
Timberwolf--Beautiful cabin near Big South Fork

Cabin #4 Secluded and Quiet

Cabin #4 Secluded and Quiet
Oneida
10.0 out of 10, Exceptional, (3 reviews)
"The cabin was BEAUTIFUL, clean and had the most amazing view. "
United States
LeeAnn B.
The price is CA $161
CA $294 total
includes taxes & fees
May 11 - May 12
Cabin #4 Secluded and Quiet

Lake Cumberland "Lake Daze Cabin" near Clearwater

Lake Cumberland "Lake Daze Cabin" near Clearwater
Nancy
9.2 out of 10, Wonderful, (5 reviews)
"Had a wonderful time!!"
United States
RICK M.
The price is CA $171
CA $298 total
includes taxes & fees
May 10 - May 11
Lake Cumberland "Lake Daze Cabin" near Clearwater
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 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?

4 Bedrooms, Heated Private pool, hot tub, Game room, and Water Front View!: Visitors like this Monticello vacation home rental. It is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a hot tub and foosball. Other favorite homes for rent in Monticello are 6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more😍 and Lake Bluff Paradise on Lake Cumberland. Game room and seasonal hot tub!.

How many vacation rentals are there in Monticello?

With 45 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, Lake Cumberland Winery and Conley Bottom Marina 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.