Monticello Cottages

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Cottages in Monticello

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

Jamestown KY

Located in Jamestown, this cottage is on a lake, a 1-minute drive from Cumberland River and 6 minutes from Jamestown Marina.

Kitchen

Washer

Unique Hexagon Cottage Atop Marina · Boat Parking · 3 En Suite Baths · Pets okay

Jamestown KY

Located in Jamestown, this cottage is on a lake, a 1-minute drive from Cumberland River and 6 minutes from Jamestown Marina.

Kitchen

Washer

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

Somerset KY

Located in Somerset, this cottage is on a lake, within a 15-minute drive of Firebrook Community Park and Somerset Mall.

Kitchen

Pet friendly

Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!

Jamestown KY

$513 nightly

$566 total

Aug 2 - Aug 3

Total with taxes and fees

Located in Jamestown, this cottage is a 1-minute drive from Cumberland River and 6 minutes from Jamestown Marina.

Hot Tub

Kitchen

Harbor Hideway is a cozy, romantic gem minutes away from Jamestown Marina!

Jamestown KY

$468 nightly

$516 total

Aug 3 - Aug 4

Total with taxes and fees

Located in Jamestown, this cottage is within a 10-minute drive of Jamestown Marina and The Links Resort Golf Course.

Hot Tub

Kitchen

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

monticello KY

When you stay at this cottage in Monticello, you'll be on the waterfront, within a 15-minute walk of Lake Cumberland Winery and Conley Bottom Marina.

Pool

Hot Tub

NEW TO VRBO May 2026 Secluded Adult themed Cottage in Kentucky

Science Hill KY

$278 nightly

$306 total

Aug 2 - Aug 3

Total with taxes and fees

Located in Science Hill, this cottage is in a rural location, within a 15-minute drive of Cave Hill Vineyard and Science Hill Baseball Park.

Hot Tub

Kitchen

Lake Daze, Blue Cottage <1mile to Jamestown Marina with space to trailer boat.

Jamestown KY

$372 nightly

$410 total

Jul 31 - Aug 1

Total with taxes and fees

When you stay at this cottage in Jamestown, you'll be on a lake, within a 5-minute drive of Jamestown Marina and Cumberland River.

Kitchen

Pet friendly

Renovated Cottage! Overlooks Dale Hollow!

Byrdstown TN

With a stay at this cottage in Byrdstown, you'll be on a lake, within a 15-minute drive of Dale Hollow Reservoir and Cordell Hull.

Kitchen

Washer

Cottage at Lake Cumberland; 6m walk to water at Clearwater public boat ramp

Nancy KY

When you stay at this cottage in Nancy, you'll be on a lake and 4 minutes by foot from Cumberland River.

Kitchen

Washer

Luxury Linens and Towels, King Size Bed hybrid pillow top mattress.

Burnside KY

Located in Burnside, this cottage is in a rural location, a 3-minute drive from Cumberland River and 9 minutes from Cole Community Park.

Kitchen

Washer

Lake Cumberland Home w/ Hot Tub & Game Room

Bronston KY

Located in Bronston, this cottage is a 1-minute drive from Cumberland River and 7 minutes from Burnside Library.

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.