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Compare 260 Vacation Homes in Monticello with updated reviews, rates, and availability.

Cozy Gray House
Exterior
Cozy Gray House
10.0 out of 10, Exceptional, (53)
"The house is cute and clean! Close to everything in Onieda, TN and to Big South Fork Entrance. Misty was nice and great at communication! I would highly recommend the gray house! recommendrecommendstaying there!!"
The price is AED 386
AED 682 total
includes taxes & fees
9 Nov - 10 Nov
Cozy Gray House
Centrally located house at Pond Meadow Place
Exterior
Centrally located house at Pond Meadow Place
9.8 out of 10, Exceptional, (29)
"House was very well kept and clean in a great neighborhood. Worked out well for our family. "
Centrally located house at Pond Meadow Place
Lake Retreat at Lake Cumberland Resort
Harmony Hideaway
Lake Retreat at Lake Cumberland Resort
9.6 out of 10, Exceptional, (162)
"We stayed for a long weekend with our teens. Nice area, plenty of space for our family, good WiFi and things to do. We found the musty odor of the home unpleasant, that isn't totally uncommon with rentals and the change of seasons. Unfortunately we were only able to use the hot tub once before it started to have issues. Andrew was very attentive to our concerns but it did spoil some of our fun. Andrew was a good host!"
Lake Retreat at Lake Cumberland Resort
6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍
Pool
6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍
9.8 out of 10, Exceptional, (19)
"Overall we enjoyed our stay here, bummed that the pool was not open as it showed in the description of the house and was the main reason for choosing the location. If it is closed for the season, list it as such. The view is great! "
6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍
Pool / Grill, Dale Hollow Lake and nearby Sunset Marina with Mountain view
Dale Hollow Lake, Private Swimming Pool and Beautiful 4 BR 3 1/2 Baths
Pool / Grill, Dale Hollow Lake and nearby Sunset Marina with Mountain view
9.6 out of 10, Exceptional, (104)
"This property was just the right size for 4 adults and 3 teenagers. We had one good day of weather and spent it on the lake, however, the girls would have loved some pictures by the pool—it looked as if maybe it was in the process of being drained and then just left. It was green and not covered for winter yet. There is a nice fire pit area that we took advantage of several nights. Bring your own chairs! The driveway is a little narrow, but has ample parking. The only other “issue” we had was...
Pool / Grill, Dale Hollow Lake and nearby Sunset Marina with Mountain view
Located on the picturesque shores of Lake Cumberland.
Interior
Located on the picturesque shores of Lake Cumberland.
9.4 out of 10, Exceptional, (3)
"It was not clean by no means. 1st the sheets looked like they hadn't been changed /washed ins while. The refrigerator was dirty,"
Located on the picturesque shores of Lake Cumberland.
3 miles from Wolf Creek Dam! Boat and camper parking available
Exterior
3 miles from Wolf Creek Dam! Boat and camper parking available
9.8 out of 10, Exceptional, (14)
"Our family loved our weekend getaway in this cabin. It felt remote and private yet still conveniently near Lake Cumberland State Park. The interior was clean and updated and plenty of essential supplies were available. The exterior had a large wrap-around porch with lots of seating. We will definitely return!"
3 miles from Wolf Creek Dam! Boat and camper parking available
LOG Cabin, 5 miles from town, but very country setting
The front of the cabin.
LOG Cabin, 5 miles from town, but very country setting
9.6 out of 10, Exceptional, (84)
"Veru nice ..clean .. in a quite area .. overall good. "
LOG Cabin, 5 miles from town, but very country setting
Lakeside Hideaway I - newly renovated lakefront with hot tub / walk to boat ramp
Outdoor spa tub
Lakeside Hideaway I - newly renovated lakefront with hot tub / walk to boat ramp
9.8 out of 10, Exceptional, (42)
"We enjoyed our stay very much. The property itself was bigger than we expected for the cost. It was very clean and was stocked with anything we needed. The bed was comfortable. We enjoyed spending time on the covered porch and in the hot tub. I would definitely stay there again, and would highly recommend it."
Lakeside Hideaway I - newly renovated lakefront with hot tub / walk to boat ramp
Russell Springs Getaway, 10 Mi to Lake Cumberland!
Russell Springs Vacation Rental | 3BR | 2BA | 2 Steps Required | 1,800 Sq Ft
Russell Springs Getaway, 10 Mi to Lake Cumberland!
10.0 out of 10, Exceptional, (8)
"The host was remarkable in communication and hospitality. We were created with hand written note, fresh farm eggs and a homemade chocolate cake. Would recommend this property and host to anyone looking for southern hospitality and clean property for their stay. "
Russell Springs Getaway, 10 Mi to Lake Cumberland!
Lovely Home Next to Dale Hollow State Park Entrance- 1 Mile to Marina
Family Room-Vaulted Ceilings Open Concept
Lovely Home Next to Dale Hollow State Park Entrance- 1 Mile to Marina
10.0 out of 10, Exceptional, (9)
"Beautiful views, clean, fast and easy communication with owner, lovely home (so cute too), just minutes from state park and marina. We so enjoyed our weekend!"
The price is AED 511
AED 1,328 total
includes taxes & fees
9 Nov - 10 Nov
Lovely Home Next to Dale Hollow State Park Entrance- 1 Mile to Marina
Mema and Pa’s Place
Exterior
Mema and Pa’s Place
10.0 out of 10, Exceptional, (2)
"Easy to find and use, beautiful home/property. Only 25 minutes from our fishing dock. The brownies were wonderful. Thank you for sharing your home with us."
The price is AED 551
AED 879 total
includes taxes & fees
10 Nov - 11 Nov
Mema and Pa’s Place
Lakeside Hideaway II - lakefront with hot tub / walk to boat ramp
Property grounds
Lakeside Hideaway II - lakefront with hot tub / walk to boat ramp
10.0 out of 10, Exceptional, (34)
"Such an amazing place to enjoy time with family!"
Lakeside Hideaway II - lakefront with hot tub / walk to boat ramp
LAKE FRONT CABIN with Large Deck.
Property grounds
LAKE FRONT CABIN with Large Deck.
10.0 out of 10, Exceptional, (29)
"We had a great experience with this stay! The cabin was immaculate! Had what we needed and not too much! The property manager communicated all information needed and was so gracious!!! "
LAKE FRONT CABIN with Large Deck.
Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!
Jamestown Vacation Rental | 4BR | 3BA | 3,400 Sq Ft | Steps Required
Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!
9.8 out of 10, Exceptional, (27)
"Great location. Great place, beautiful views"
Luxe Lake Cumberland Retreat w/ Decks on 1 Acre!
Little blue house on the lake
Terrace/patio
Little blue house on the lake
9.4 out of 10, Exceptional, (9)
"Place was great! Place was clean upon arrival with great communication with property owner. Would definitely recommend! Thanks for the stay!"
Little blue house on the lake
Spacious 5-Bedroom Home on Lake Cumberland!
Living area
Spacious 5-Bedroom Home on Lake Cumberland!
10.0 out of 10, Exceptional, (8)
"We had a wonderful weekend! This is a beautiful space. That master bedroom is incredible!! 5-Star!!"
Spacious 5-Bedroom Home on Lake Cumberland!
River-View Somerset Home: Large Deck, Fire Pit!
Somerset Vacation Rental | 3BR | 2.5BA | 2,000 Sq Ft | Stairs Required
River-View Somerset Home: Large Deck, Fire Pit!
9.6 out of 10, Exceptional, (22)
"Wow. This is a gem in Pulaski. The views of Cumberland are amazing and the sunsets were breathtaking. "
River-View Somerset Home: Large Deck, Fire Pit!
Ellie’s Place - Woodsy Retreat! Book now and enjoy.
Exterior
Ellie’s Place - Woodsy Retreat! Book now and enjoy.
9.8 out of 10, Exceptional, (115)
"We stayed the weekend of the big storm so we lost power the first night. It was out for a little over an hour that could not be helped. There were no flashlights or lanterns on property to use. I called and was told to check with security. My understanding is that this problem will be fixed. We then had to call to have the battery changed in the smoke detector and while we were waiting for the maintenance man to get there, we saw a roach crawl across the kitchen floor. When the maintenance...
Ellie’s Place - Woodsy Retreat! Book now and enjoy.
Enjoy your Perfect Getaway near Lake Cumberland! Pet Friendly with a Hot Tub!
The Enchanted Hideaway Cabin is located in the beautiful Lake Cumberland resort.
Enjoy your Perfect Getaway near Lake Cumberland! Pet Friendly with a Hot Tub!
9.8 out of 10, Exceptional, (195)
"Nice and peaceful! Very quiet. This was our 2nd time in this cabin. We come down every 2 years. "
Enjoy your Perfect Getaway near Lake Cumberland! Pet Friendly with a Hot Tub!
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

This charming cozy cottage has a private hot tub, deck for fishing.
pond and fishing deck in back yard
This charming cozy cottage has a private hot tub, deck for fishing.
9.8 out of 10, Exceptional, (142)
"Was a great stay. Nice place, deck over a pond. Owner was great communication. highly recommend."
This charming cozy cottage has a private hot tub, deck for fishing.
6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍
Pool
6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍
9.8 out of 10, Exceptional, (19)
"Overall we enjoyed our stay here, bummed that the pool was not open as it showed in the description of the house and was the main reason for choosing the location. If it is closed for the season, list it as such. The view is great! "
6 Bedroom home, private pool, person Hot tub, Waterfront Views, and more!😍
Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!
Fall colors on the Bluff!
Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!
10.0 out of 10, Exceptional, (104)
"We enjoyed sitting on the screened-in patio overlooking the river watching the falling leaves float to the ground. Watched a group of 15 wild turkeys make the way way past the property. their wwa"
Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!
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.