Photo by Lisa Klein

Holiday Homes in Monticello

Start date: Check-in selected.
To Date
End date: Check-out
    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

In two weeks
10 Oct - 12 Oct
In two months
21 Nov - 23 Nov
In three months
19 Dec - 21 Dec
In four months
16 Jan - 18 Jan

Featured Holiday Homes in Monticello and around

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

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

9.8 out of 10, Exceptional, (30)
"We only stayed a short time but really enjoyed the pool and hot tub. The lake view and fire pit were a hit as well! "
6 Bedroom home, heated private pool, person Hot tub, Waterfront Views, and more😍
Cumberland Lake House
Exterior

Cumberland Lake House

Cumberland Lake House
Boating Mecca: Near Dale Hollow Lake & Golf!
Outdoor dining

Boating Mecca: Near Dale Hollow Lake & Golf!

10.0 out of 10, Exceptional, (81)
"Everything was top notch. We will definitely stay here again for future trips. "
The price is €154
includes taxes & fees
8 Oct - 9 Oct
Boating Mecca: Near Dale Hollow Lake & Golf!
3 miles from Wolf Creek Dam! Boat and camper parking available
Exterior

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

9.6 out of 10, Exceptional, (30)
"Went fishing at Wolf Creek Dam , Drove over to Tennessee of shopping and dinner but enjoyed the stay at the cabin "
3 miles from Wolf Creek Dam! Boat and camper parking available
White Oak Cottage - Resort Pool, Boat Slip
Fridge, microwave, oven, stovetop

White Oak Cottage - Resort Pool, Boat Slip

10.0 out of 10, Exceptional, (5)
"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. "
The price is €339
includes taxes & fees
1 Oct - 2 Oct
White Oak Cottage - Resort Pool, Boat Slip
Cozy 2-bedroom house in Jamestown with AC, WiFi
Interior

Cozy 2-bedroom house in Jamestown with AC, WiFi

10.0 out of 10, Exceptional, (4)
"We had a great time. The owner, Andrea is super great. The home was private, clean, and perfect for us. Only 5 minutes from town and our grandson. Had a quick but perfect trip. Thank you for letting us stay!! "
The price is €160
includes taxes & fees
29 Sept - 30 Sept
Cozy 2-bedroom house in Jamestown with AC, WiFi
4 Bedrooms, Heated Private pool, hot tub, Game room, and Water Front View!
Smart TV, fireplace, table football

4 Bedrooms, Heated Private pool, hot tub, Game room, and Water Front View!

9.6 out of 10, Exceptional, (102)
"Great house and lost of fun things to do!"
4 Bedrooms, Heated Private pool, hot tub, Game room, and Water Front View!
Cozy Lakehouse – Game Room, Pet-Friendly, Near Boatramp, 3-Season room!
Property grounds

Cozy Lakehouse – Game Room, Pet-Friendly, Near Boatramp, 3-Season room!

2.0 star property
9.8 out of 10, Exceptional, (7)
"The property was great for a group trip and we enjoyed the amenities provided."
The price is €360
includes taxes & fees
28 Sept - 29 Sept
Cozy Lakehouse – Game Room, Pet-Friendly, Near Boatramp, 3-Season room!
The Holiday Hutt at Dale Hollow Lake-Close to Sunset, Bball Court, Movie Theater
Terrace/patio

The Holiday Hutt at Dale Hollow Lake-Close to Sunset, Bball Court, Movie Theater

10.0 out of 10, Exceptional, (12)
"The home was amazing. Considering returning next summer with a few families. "
The price is €1,919
includes taxes & fees
26 Oct - 27 Oct
The Holiday Hutt at Dale Hollow Lake-Close to Sunset, Bball Court, Movie Theater
Lake View Home, Fire Pit, Grill, Fireplace, 5 minutes to boat ramp
Miscellaneous

Lake View Home, Fire Pit, Grill, Fireplace, 5 minutes to boat ramp

9.2 out of 10, Wonderful, (93)
"Had a great stay"
Lake View Home, Fire Pit, Grill, Fireplace, 5 minutes to boat ramp
Driftwood Cottage Lake Cumberland Retreat with hot tub & water access!
Outdoor spa tub

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

9.4 out of 10, Exceptional, (13)
"The property was clean. The rooms were nice."
Driftwood Cottage Lake Cumberland Retreat with hot tub & water access!
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, (189)
"This was a great place to stay. "
Lake Days & Starry Nights – Your Perfect Getaway Awaits
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, (43)
"Great comfortable bed.Boat launch close ."
Lakeside Hideaway II - lakefront with hot tub / walk to boat ramp
Lake house with boat ramp access across the street & tons of boat parking space.
Fridge, microwave, oven, stovetop

Lake house with boat ramp access across the street & tons of boat parking space.

9.8 out of 10, Exceptional, (79)
"We’ve stayed at this awesome property for a couple years and will definitely return!"
Lake house with boat ramp access across the street & tons of boat parking space.
3 bdrm/2 full bath home 1.5 miles from Wolf Creek Marina, Lake Cumberland
Exterior

3 bdrm/2 full bath home 1.5 miles from Wolf Creek Marina, Lake Cumberland

10.0 out of 10, Exceptional, (5)
"First time staying at this property and on this side of the lake! House was super cute on a dead end road.Very quiet location and close to the marina if your planning to visit beautiful Lake Cumberland! Will definitely recommend this place! Super clean and well stocked property. "
3 bdrm/2 full bath home 1.5 miles from Wolf Creek Marina, Lake Cumberland
Enjoy your Perfect Getaway near Lake Cumberland! Pet Friendly with a Hot Tub!
Outdoor dining

Enjoy your Perfect Getaway near Lake Cumberland! Pet Friendly with a Hot Tub!

9.8 out of 10, Exceptional, (208)
"Very nice place in an excellent location. We spent our 25th anniversary there and can’t wait to go back "
Enjoy your Perfect Getaway near Lake Cumberland! Pet Friendly with a Hot Tub!
Lake Lovers Paradise
Terrace/patio

Lake Lovers Paradise

8.4 out of 10, Very good, (11)
"Nice, quite and convenient place to stay "
Lake Lovers Paradise
Cozy 1-bedroom house in charming Allardt with AC, WiFi
Dining

Cozy 1-bedroom house in charming Allardt with AC, WiFi

10.0 out of 10, Exceptional, (6)
"Very nicely set up for a getaway place and perfect for me to be close to why I choose this place, If I come back for the Rugby Rumble at the RM Brooks store and it is open I would stay here again. Thank you to the Yorks"
The price is €109
includes taxes & fees
29 Sept - 30 Sept
Cozy 1-bedroom house in charming Allardt with AC, WiFi
Garrett's Private Lake House with Horse Barn in wonderful Jamestown;
TV

Garrett's Private Lake House with Horse Barn in wonderful Jamestown;

Garrett's Private Lake House with Horse Barn in wonderful Jamestown;
Charming 3-bedroom house with WiFi, AC just 2 miles from Dale Hallow lake
Fridge, microwave, oven, stovetop

Charming 3-bedroom house with WiFi, AC just 2 miles from Dale Hallow lake

10.0 out of 10, Exceptional, (2)
"Lovely little home; convenient to Albany, KY and Byrdstown, TN."
Charming 3-bedroom house with WiFi, AC just 2 miles from Dale Hallow lake
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Monticello Hotel Reviews

Hampton Inn Somerset

Hampton Inn Somerset

10/10 Excellent
"Suited our needs for the night. Liked that the rooms were quiet. The pillows are excellent!"
bill 1-night trip
Posted 5 days ago
Hampton Inn Somerset

Find out more about Monticello

Find out more about Monticello

Monticello Holiday Homes information

Number of reviews
848
Accommodation
328 Holiday Homes
Lowest Price
€109
Highest Price
€1,919

Explore a world of travel with Expedia

Explore a world of travel with Expedia