Monticello Vacation Rentals

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Vacation Rentals in Monticello

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

Allardt TN

$120 nightly

$135 total

Jan 1 - Jan 2, 2026

Total with taxes and fees

This vacation home is 6 mi (9.7 km) from Allardt Town Hall and 6 mi (9.7 km) from Colditz Cove State Natural Area.

Kitchen

Washer

Cumberland Lake House

Nancy KY

When you stay at this vacation home in Nancy, you'll be 7 minutes by car from Cumberland Point Recreation Area.

Kitchen

Washer

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

Monticello KY

Located in Monticello, this vacation home is within a 15-minute drive of Cumberland River and Burnside Library.

Pool

Hot Tub

Amazing 5BR House with Lake & Mountain Views in Gated Resort

Burnside KY

With a stay at this vacation home in Burnside, you'll be on a lake, and 9.7 mi (15.5 km) from Cumberland River and 9.9 mi (16 km) from Burnside Marina.

Pool

Kitchen

Lakeside Hideaway I - newly renovated lakefront with hot tub / walk to boat ramp

Burnside KY

With a stay at this vacation home in Burnside, you'll be on the waterfront, and 10.6 mi (17 km) from Cumberland River and 11.1 mi (17.9 km) from Burnside Marina.

Pool

Hot Tub

Remodeled House Near Jamestown Marina, Room to Park Your Boat in Driveway!

Jamestown KY

$357 nightly

$394 total

Dec 14 - Dec 15

Total with taxes and fees

Located in Jamestown, this vacation home is a 5-minute drive from Jamestown Marina and 5 minutes from Cumberland River.

Hot Tub

Kitchen

White Oak Cottage - Resort Pool, Boat Slip

Burnside KY

$343 nightly

$386 total

Dec 14 - Dec 15

Total with taxes and fees

With a stay at this vacation home in Somerset, you'll be on a lake, a 5-minute walk from Cumberland River and a 3-minute drive from Burnside Library.

Pool

Kitchen

Lake house. Less than 3 miles from beautiful Lake Cumberland.

Jamestown KY

$224 nightly

$247 total

Dec 14 - Dec 15

Total with taxes and fees

When you stay at this vacation home in Jamestown, you'll be on a lake, within a 10-minute walk of Judicial Center Fountain Park and The Park at Jamestown Square.

Hot Tub

Kitchen

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

Jamestown KY

$558 nightly

$615 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

When you stay at this vacation home in Jamestown, you'll be on the waterfront, within a 5-minute drive of The Park at Jamestown Square and Judicial Center Fountain Park.

Kitchen

Washer

Large 8 Bedroom Home Overlooking Play Area, And Pool. Great For Family Reunions.

Monticello KY

Located in Monticello, this vacation home is in a rural location, within a 15-minute walk of Lake Cumberland Winery and Conley Bottom Marina.

Pool

Kitchen

4 Bedrooms, Heated Private pool, hot tub, Game room, and Water Front View!

Monticello KY

Located in Monticello, this vacation home is on a lake, within a 15-minute drive of Cumberland River and Burnside Library.

Pool

Hot Tub

Wet Feet Retreat is a family friendly home near Burnside Island State Park.

Burnside KY

Located in Burnside, this vacation home is on a lake, within a 10-minute drive of Burnside Library and Burnside Marina.

Kitchen

Washer

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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.