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Vacation Homes in Monticello

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

10.0 out of 10, Exceptional, (145)
"Great Experience on the property and on the Lake!! "
LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.

Cumberland Haven! One mile to Cumberland Point boat ramp and park.

10.0 out of 10, Exceptional, (7)
Cumberland Haven! One mile to Cumberland Point boat ramp and park.

Historic Union Chapel Elementary School near Cumberland River & Lake

10.0 out of 10, Exceptional, (35)
"Very nice accommodation not far from Jamestown the owner greeted me when i arrived and coffee and snacks were available I would recommend this great opportunity for anyone that is going to Jamestown "
$120 nightly
The price is $132
Aug 11 - Aug 12
Total includes taxes and fees
Historic Union Chapel Elementary School near Cumberland River & Lake

Conner Room Lakeside Inn at Dale Hollow - newly renovated near Dale Hollow Lake!

9.8 out of 10, Exceptional, (18)
"Great place to stay if fishing dale hollow. Convenient parking and close to boat ramps and tackle shops. "
Conner Room Lakeside Inn at Dale Hollow - newly renovated near Dale Hollow Lake!

LAKE CUMBERLAND Get-a-Way! Charming House. BOAT RAMP NEARBY - Wifi - RV Hookups

10.0 out of 10, Exceptional, (2)
"Everglow Hollow was great! We stayed for a long weekend and it was the perfect place to relax, while not being too far away from Lake Cumberland. Host also responded to questions right away and were very helpful. "
$166 nightly
The price is $183
Aug 11 - Aug 12
Total includes taxes and fees
LAKE CUMBERLAND Get-a-Way! Charming House. BOAT RAMP NEARBY - Wifi - RV Hookups

Cumberland Lake House

Cumberland Lake House

Near Lake Cumberland: Monticello Home w/ Gazebo!

10.0 out of 10, Exceptional, (2)
"We really enjoyed our stay at this cute bungalow! It was cozy, clean, and conveniently located—just a quick 10-minute drive to either Conley Bottom or Monticello. The street was quiet and peaceful, perfect for a relaxing getaway. Would definitely stay again!"
Near Lake Cumberland: Monticello Home w/ Gazebo!

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

10.0 out of 10, Exceptional, (116)
"First impression was wow. Very clean, beautiful location and a great game room. Very accommodation owners."
Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!

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

10.0 out of 10, Exceptional, (2)
"We came in town for a surprise birthday party and this home was perfect for our whole family. The home has an amazing view of the lake and was stocked with everything we needed. The host was very responsive and even left a small gift to help us celebrate. The hospitality was greatly appreciated and my family had such a special weekend celebrating together. Looking forward to coming back!! "
NEW! Lake Fun: 6BR + Hot Tub + Game Room

3 miles from Wolf Creek Dam! Boat and camper parking available

9.6 out of 10, Exceptional, (27)
"The property is beautiful. The place is cozy and clean."
3 miles from Wolf Creek Dam! Boat and camper parking available

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

10.0 out of 10, Exceptional, (8)
"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

White Oak Cottage - Resort Pool, Boat Slip

10.0 out of 10, Exceptional, (3)
"This place is a beautiful new build that has everything you will ever need for any length of stay. Highly recommended for anyone visiting the area. We really liked the location, and the fact that all our entertainment was very close. "
$429 nightly
The price is $483
Aug 10 - Aug 11
Total includes taxes and fees
White Oak Cottage - Resort Pool, Boat Slip

Spectacular 3BR Home Close To Beautiful Lake Cumberland!

2.0 star property
10.0 out of 10, Exceptional, (2)
"Very clean and in a great location to get to the lake. We enjoyed the stay!"
Spectacular 3BR Home Close To Beautiful Lake Cumberland!

Lake-Front Woodson Bend 14-1

9.8 out of 10, Exceptional, (167)
"Easy to find, clear and direct instructions for locating and checking in. Super clean, everything we needed, and perfect for a quick weekend getaway!"
Lake-Front Woodson Bend 14-1

Cozy Lake Cumberland Lakeview Shangri-la

9.6 out of 10, Exceptional, (15)
"We had a great stay. The house was beautiful and well appointed. Had a great visit. "
$393 nightly
The price is $433
Aug 18 - Aug 19
Total includes taxes and fees
Cozy Lake Cumberland Lakeview Shangri-la

Cozy 2-bedroom house in Jamestown with AC, WiFi

10.0 out of 10, Exceptional, (3)
"We had an amazing stay. Host was quick to respond, although we didn't really need anything. For the most part we had a great stay. I was surprised that it was duplex not a house,but it didnt effect our stay. Would definitely stay again!!"
$192 nightly
The price is $216
Aug 11 - Aug 12
Total includes taxes and fees
Cozy 2-bedroom house in Jamestown with AC, WiFi

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

2.0 star property
10.0 out of 10, Exceptional, (9)
"Really nice! Highly recommend!"
$155 nightly
The price is $171
Aug 11 - Aug 12
Total includes taxes and fees
Calming 1-bedroom yellow door house close to lake with Wi-Fi, AC

Near Cumberland River, 12 miles from Wolf Creek Dam, in Creelsboro community

9.6 out of 10, Exceptional, (49)
"Easily accessible and the hosts are great communicators for everything. "
Near Cumberland River, 12 miles from Wolf Creek Dam, in Creelsboro community

Home Near Dale Hollow Lake: Deck & Fire Pit

9.6 out of 10, Exceptional, (7)
Home Near Dale Hollow Lake: Deck & Fire Pit

Family friendly 4-bedroom home with room for multiple boat trailers in Somerset

10.0 out of 10, Exceptional, (3)
"Excellent property, very convenient location."
Family friendly 4-bedroom home with room for multiple boat trailers in Somerset
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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Top Monticello Hotel Reviews