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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

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

Lake Days & Starry Nights – Your Perfect Getaway Awaits
Indoor spa tub

Lake Days & Starry Nights – Your Perfect Getaway Awaits

9.6 out of 10, Exceptional, (174)
"This was a great place to stay. "
Lake Days & Starry Nights – Your Perfect Getaway Awaits
Lake Cumberland Luxury #2! Amazing Lake views, hot tub, fire pit!
Terrace/patio

Lake Cumberland Luxury #2! Amazing Lake views, hot tub, fire pit!

10.0 out of 10, Exceptional, (2)
"Excellent bang for your buck! Truly a wonderful stay and great for the price! I will DEFINITELY be trying to come back again! Stay with confidence! "
Lake Cumberland Luxury #2! Amazing Lake views, hot tub, fire pit!
Boating Mecca: Near Dale Hollow Lake & Golf!
Outdoor dining

Boating Mecca: Near Dale Hollow Lake & Golf!

10.0 out of 10, Exceptional, (72)
"This is the best VRBO that we've stayed in. The fresh baked cookies when we walked in the door. The cleanliness was excellent. The home was well decorated, and the master bed was incredible. Highly recommend. We will be booking with them next time."
The price is AED 334
AED 686 total
includes taxes & fees
12 May - 13 May
Boating Mecca: Near Dale Hollow Lake & Golf!
Luxe Lake Barndo w/ 2 King Suites! Hot Tub, Fire Pit, 1/8 mile to boat ramp!
Outdoor spa tub

Luxe Lake Barndo w/ 2 King Suites! Hot Tub, Fire Pit, 1/8 mile to boat ramp!

10.0 out of 10, Exceptional, (19)
"Perfect location, clean and the host are friendly and very responsive. "
The price is AED 995
AED 2,027 total
includes taxes & fees
1 May - 2 May
Luxe Lake Barndo w/ 2 King Suites! Hot Tub, Fire Pit, 1/8 mile to boat ramp!
Hideaway 27
3 bedrooms, desk, iron/ironing board, free WiFi

Hideaway 27

10.0 out of 10, Exceptional, (25)
"Cozy, comfortable, and all around a GREAT STAY!!!"
The price is AED 397
AED 902 total
includes taxes & fees
12 May - 13 May
Hideaway 27
Little blue house on the lake
Interior

Little blue house on the lake

9.6 out of 10, Exceptional, (14)
"The property was very clean well organized in a home away from home."
Little blue house on the lake
Pool / Grill, Dale Hollow Lake and nearby Sunset Marina with Mountain view
Terrace/patio

Pool / Grill, Dale Hollow Lake and nearby Sunset Marina with Mountain view

9.6 out of 10, Exceptional, (104)
"Once again a Great family vacation. Plenty of parking for vehicles and boats. Close to marinas the pool was a great plus for the grandkids and house was perfect for all of us."
Pool / Grill, Dale Hollow Lake and nearby Sunset Marina with Mountain view
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
6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍
Interior

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

10.0 out of 10, Exceptional, (21)
"We had a great time at this spacious, well equipped house with lake view. Great location to marina."
6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍
⚓ 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
2 May - 3 May
⚓ Anchor Down ⚓ Spacious lakefront home on Lake Cumberland - W/ PRIVATE SLIP!
Lake Cumberland Home 1/2 Mi to Beaver Creek Marina
Outdoor dining

Lake Cumberland Home 1/2 Mi to Beaver Creek Marina

9.2 out of 10, Wonderful, (62)
"The stay was great. Location related to the beavercreek marina was perfect!"
Lake Cumberland Home 1/2 Mi to Beaver Creek Marina
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, (86)
"The property was "
Amazing 5BR House with Lake & Mountain Views in Gated Resort
NEW! Lake Fun: 6BR + Hot Tub + Game Room
Exterior

NEW! Lake Fun: 6BR + Hot Tub + Game Room

10.0 out of 10, Exceptional, (1)
"Great space! Had everything we needed and more. "
NEW! Lake Fun: 6BR + Hot Tub + Game Room
1-Mile from Conley Bottom's ramp
Smart TV, books

1-Mile from Conley Bottom's ramp

9.8 out of 10, Exceptional, (32)
"We had a great stay. It was close to the dock, clean, plenty of space, nice pond view. Would stay again."
1-Mile from Conley Bottom's ramp
Lake-Front Woodson Bend 14-1
Property grounds

Lake-Front Woodson Bend 14-1

9.8 out of 10, Exceptional, (165)
"The condo was absolutely perfect. It had everything we needed in an absolute perfect setting. The community is amazing! The bed was the most comfortable bed I have ever had in any VRBO. "
Lake-Front Woodson Bend 14-1
Pet & Family Friendly • Near Lake • HotTub • FirePit • Game Room • Close to town
Game room

Pet & Family Friendly • Near Lake • HotTub • FirePit • Game Room • Close to town

10.0 out of 10, Exceptional, (2)
"Host was wonderful to deal with. Very quick communication. House was very lovely. Towels, bedding, and beds were all great quality. We got to explore the area some, and have some good family time by the fire pit and outdoor area during our stay.I did have one wish but no complaints whatsoever and that would be a bathroom upstairs. Would definitely book again."
Pet & Family Friendly • Near Lake • HotTub • FirePit • Game Room • Close to town
Centrally located house at Pond Meadow Place
Fridge, microwave, oven, stovetop

Centrally located house at Pond Meadow Place

9.6 out of 10, Exceptional, (34)
"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
Captivating 2-bedroom, garage door house with WiFi, AC in welcoming Somerset
Outdoor dining

Captivating 2-bedroom, garage door house with WiFi, AC in welcoming Somerset

2.0 star property
9.8 out of 10, Exceptional, (8)
"The host was great & accommodated to what we needed! The place was clean & comfortable! Would stay again! "
The price is AED 551
AED 688 total
includes taxes & fees
4 May - 5 May
Captivating 2-bedroom, garage door house with WiFi, AC in welcoming Somerset
Calming 1-bedroom yellow door house close to lake with Wi-Fi, AC
Terrace/patio

Calming 1-bedroom yellow door house close to lake with Wi-Fi, AC

2.0 star property
10.0 out of 10, Exceptional, (4)
"Really nice! Highly recommend!"
The price is AED 496
AED 628 total
includes taxes & fees
4 May - 5 May
Calming 1-bedroom yellow door house close to lake with Wi-Fi, AC
Vacationers' Delight at Conley Bottom

Vacationers' Delight at Conley Bottom

10.0 out of 10, Exceptional, (50)
"We had a great time being so close to Conley Bottom."
Vacationers' Delight at Conley Bottom
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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Other property types in Monticello

Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!
Outdoor spa tub

Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!

10.0 out of 10, Exceptional, (106)
"Pleasant quiet area to stay"
Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!
Luxe Lake Barndo w/ 2 King Suites! Hot Tub, Fire Pit, 1/8 mile to boat ramp!
Outdoor spa tub

Luxe Lake Barndo w/ 2 King Suites! Hot Tub, Fire Pit, 1/8 mile to boat ramp!

10.0 out of 10, Exceptional, (19)
"Perfect location, clean and the host are friendly and very responsive. "
The price is AED 995
AED 2,027 total
includes taxes & fees
1 May - 2 May
Luxe Lake Barndo w/ 2 King Suites! Hot Tub, Fire Pit, 1/8 mile to boat ramp!
This charming cozy cottage has a private hot tub, deck for fishing.
Property grounds

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

9.8 out of 10, Exceptional, (146)
"We would like to stay there again because of all the amenities the manager was very friendly"
This charming cozy cottage has a private hot tub, deck for fishing.
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.