Photo by Lisa Klein

Search Vacation Homes in Monticello

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

Compare 325 Vacation Homes in Monticello with updated reviews, rates, and availability.

“Red’s House” located in Oneida city limits
Exterior

“Red’s House” located in Oneida city limits

10.0 out of 10, Exceptional, (31)
"This property is in excellent condition and well managed. I will stay here again."
The price is AED 386
AED 770 total
includes taxes & fees
12 Jun - 13 Jun
“Red’s House” located in Oneida city limits
Lake Cumberland Hideaway #1-2 miles from Jtown Marina! Boat Parking & Fire Pit!
View from property

Lake Cumberland Hideaway #1-2 miles from Jtown Marina! Boat Parking & Fire Pit!

10.0 out of 10, Exceptional, (156)
"We had a great time here, was clean, and convenient!"
Lake Cumberland Hideaway #1-2 miles from Jtown Marina! Boat Parking & Fire Pit!
Lakeside Hideaway II - lakefront with hot tub / walk to boat ramp
Fridge, microwave, oven, stovetop

Lakeside Hideaway II - lakefront with hot tub / walk to boat ramp

10.0 out of 10, Exceptional, (37)
"We had a great time and the accommodations were great Thank you Tracy"
Lakeside Hideaway II - lakefront with hot tub / walk to boat ramp
Cumberland Get-A-Way located at entrance of State Park
Property grounds

Cumberland Get-A-Way located at entrance of State Park

10.0 out of 10, Exceptional, (16)
"We had a really nice time at Brandon’s place! Everything we needed. He was wonderful to work with too. It’s perfect for a large family and so close to State park and the dam, for getting in the water."
Cumberland Get-A-Way located at entrance of State Park
Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!
Property grounds

Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!

9.8 out of 10, Exceptional, (32)
"Great place to hang out with family."
Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!
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, (70)
"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.
Dale Hollow Cabin Next To State Park With Free Fire Pit & COVERED Boat Slip
Outdoor dining

Dale Hollow Cabin Next To State Park With Free Fire Pit & COVERED Boat Slip

9.8 out of 10, Exceptional, (72)
"Very clean and nice property very close to Dale Hollow golf course. Host was very accommodating. Will stay here again if possible. "
Dale Hollow Cabin Next To State Park With Free Fire Pit & COVERED Boat Slip
Peaceful Days at The Barn in Alpine
Smart TV, fireplace

Peaceful Days at The Barn in Alpine

10.0 out of 10, Exceptional, (9)
"Wonderful place to stay and meet up with old friends"
The price is AED 367
AED 824 total
includes taxes & fees
3 Jun - 4 Jun
Peaceful Days at The Barn in Alpine
Cozy 1-bedroom Tiny House with WiFi, AC in beautiful Somerset
Fridge, microwave, oven, stovetop

Cozy 1-bedroom Tiny House with WiFi, AC in beautiful Somerset

2.0 star property
The price is AED 404
AED 631 total
includes taxes & fees
3 Jun - 4 Jun
Cozy 1-bedroom Tiny House with WiFi, AC in beautiful Somerset
Little blue house on the lake
Interior

Little blue house on the lake

9.6 out of 10, Exceptional, (15)
"The property was very clean well organized in a home away from home."
Little blue house on the lake
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, (137)
"Was everything we were looking for. The view was amazing. The local was close to stores and restaurants. The home had everything we needed. "
LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY
Lake Days & Starry Nights – Your Perfect Getaway Awaits
Indoor spa tub

Lake Days & Starry Nights – Your Perfect Getaway Awaits

9.8 out of 10, Exceptional, (177)
"This was a great place to stay. "
Lake Days & Starry Nights – Your Perfect Getaway Awaits
Gorgeous new 3 bdr house right by entrance to Dale Hollow Lake State Resort Park
Exterior

Gorgeous new 3 bdr house right by entrance to Dale Hollow Lake State Resort Park

10.0 out of 10, Exceptional, (3)
"The location and house were excellent for our needs. We would definitely book this rental again"
Gorgeous new 3 bdr house right by entrance to Dale Hollow Lake State Resort Park
Luxury Laurel Lake Retreat-Private Home Near Holly Bay w Fishing Pond EV CHARGER
Interior

Luxury Laurel Lake Retreat-Private Home Near Holly Bay w Fishing Pond EV CHARGER

10.0 out of 10, Exceptional, (2)
" Everything about the place was excellent from the house itself to the location. It was perfect"
Luxury Laurel Lake Retreat-Private Home Near Holly Bay w Fishing Pond EV CHARGER
⚓ 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)
"Could not have been better. Hope to return soon."
The price is AED 2,755
AED 3,932 total
includes taxes & fees
3 Jun - 4 Jun
⚓ Anchor Down ⚓ Spacious lakefront home on Lake Cumberland - W/ PRIVATE SLIP!
Driftwood Cottage Lake Cumberland Retreat with hot tub & water access!
Outdoor spa tub

Driftwood Cottage Lake Cumberland Retreat with hot tub & water access!

8.8 out of 10, Excellent, (5)
"The property was clean. The rooms were nice."
Driftwood Cottage Lake Cumberland Retreat with hot tub & water access!
Centrally located house at Pond Meadow Place
Fridge, microwave, oven, stovetop

Centrally located house at Pond Meadow Place

9.6 out of 10, Exceptional, (35)
"This is our second time staying in this home. It's a great home and convenient to everything. The neighborhood is very quiet and well kept. Highly recommend this property to everyone! "
Centrally located house at Pond Meadow Place
Amazing 5BR House with Lake & Mountain Views in Gated Resort
Outdoor dining

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

10.0 out of 10, Exceptional, (88)
"The property was "
Amazing 5BR House with Lake & Mountain Views in Gated Resort
Ellie's Place: Best Rates Ever! Bring your boat or ATV!
Outdoor dining

Ellie's Place: Best Rates Ever! Bring your boat or ATV!

9.8 out of 10, Exceptional, (120)
"Cabin had everything: hot tub, pool table, propane grill, projection TV, well stocked kitchen! New cabin in a great location! We will definitely be back!"
Ellie's Place: Best Rates Ever! Bring your boat or ATV!
"Eagle's Cliff" at Lake Cumberland. Relaxing Beautiful Front Porch Lake View!
Fridge, microwave, oven, stovetop

"Eagle's Cliff" at Lake Cumberland. Relaxing Beautiful Front Porch Lake View!

9.4 out of 10, Exceptional, (9)
"What we enjoyed the most was sitting on the deck and taking in the view of Lake Cumberland. It's a quiet and cozy place on a lightly-traveled road way out in the country."
"Eagle's Cliff" at Lake Cumberland. Relaxing Beautiful Front Porch Lake View!
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free