Monticello Cottages

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Check dates for Monticello hotels

Cottages in Monticello

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

LAKE CUMBERLAND, ROMANTIC HOT TUB, FENCED YARD, RELAXATION, 100 meg WIFI

Somerset KY

Located in Somerset, this cottage is in the mountains, within a 10-minute drive of Flashback Theater Company and Rosewood Neighborhood Park.

Hot Tub

Kitchen

NEW TO VRBO May 2026 Secluded Adult themed Cottage in Kentucky

Science Hill KY

$326 nightly

$359 total

Sep 21 - Sep 22

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

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

Jamestown KY

$357 nightly

$393 total

Sep 28 - Sep 29

Total with taxes and fees

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

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

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

Restful Rustic Farmhouse on Lake Cumberland

Jamestown KY

$734 nightly

$809 total

Sep 23 - Sep 24

Total with taxes and fees

Located in Jamestown, this cottage is on a lake, a 4-minute drive from The Links Resort Golf Course and 5 minutes from The Park at Jamestown Square.

Hot Tub

Kitchen

Unwind Near the Lake Fire Pit Marina Nearby

Bronston KY

Located in Bronston, this cottage is a 2-minute drive from Cumberland River and 6 minutes from Burnside Library.

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

Cumberland Blue- Cozy, Rustic Cottage Near Lake Cumberland

Jamestown KY

When you stay at this cottage in Jamestown, you'll be within a 10-minute drive of Judicial Center Fountain Park and The Park at Jamestown Square.

Kitchen

Washer

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

Jamestown KY

$452 nightly

$498 total

Oct 4 - Oct 5

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

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

Don't see what you're looking for?

See all available properties in Monticello

View all properties

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.