Photo by Lisa Klein

Search Cottages in Monticello

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 115 Cottages in Monticello with updated reviews, rates, and availability.

JAMESTOWN Marina, LCKY. boat parking. pool table. 3 full baths. pet friendly.

10.0 out of 10, Exceptional, (163)
"Enjoyed our time relaxing and spending time together away from responsibilities. Quiet and comfy. "
JAMESTOWN Marina, LCKY. boat parking. pool table. 3 full baths. pet friendly.

NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking

10.0 out of 10, Exceptional, (34)
"Beautiful views of the lake, clean and comfortable beds. Overall perfect quiet retreat for me. Will be back again!"
NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking

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

9.8 out of 10, Exceptional, (146)
"Quite place to kick back and relax, says you can fish there is a private deck at the home, but there is so many turtles in the pond they have ate all the fish. But not the owners fault, just a heads up on the private fishing dock. "
This charming cozy cottage has a private hot tub, deck for fishing.

Lake Front Home with community boat ramp. Private, close to marinas and town.

9.6 out of 10, Exceptional, (215)
"Nice and cozy. We enjoyed the beautiful view. Very clean and had everything you need to unplug and relax. "
Lake Front Home with community boat ramp. Private, close to marinas and town.

Dale Hollow Cottage w/ Covered Porch & Lake Views!

10.0 out of 10, Exceptional, (8)
"This house had everything we needed to enjoy our vacation at the lake. The important things for us on vacation is sleeping comfortably, a great view and the location close to the state park. We loved the back porch overlooking part of the lake and hills. The beds were very comfortable especially the king in the master. Great place to stay!"
Dale Hollow Cottage w/ Covered Porch & Lake Views!

COUNTRY PEACEFUL, FENCED YARD, FIRE PIT, HOT TUB, 100 meg internet, FIREPLACE

10.0 out of 10, Exceptional, (236)
"We absolutely loved our stay! The house is clean, cozy, and full of charm. You can truly feel the care and love the owner has put into every detail to ensure guests have a peaceful, relaxing experience. She was incredibly friendly and responsive, which made everything even smoother. The views from the hot tub and fire pit—overlooking a picturesque hillside with grazing livestock—were simply beautiful. Our dogs had the time of their lives running around the spacious, fenced-in backyard. We...
COUNTRY PEACEFUL, FENCED YARD, FIRE PIT, HOT TUB, 100 meg internet, FIREPLACE

Restful Rustic Farmhouse on Lake Cumberland

8.8 out of 10, Excellent, (5)
"We booked last minute and were suprised to find this availability. 9 adults and 3 children had plenty of room to spread out. We weren't there long enough to cook and enjoy all the house had to offer, so I can't comment on the amenities. Joe was gracious to let us check in a little early. Responsive to all msgs. Would definitely book again with the hope to stay longer next time!"
The price is AED 1,653
AED 2,891 total
includes taxes & fees
16 Apr - 17 Apr
Restful Rustic Farmhouse on Lake Cumberland

Cozy cabin minutes from Lake Cumberland with room for your boat.

10.0 out of 10, Exceptional, (19)
"Enjoyed the peace and quiet. Very clean and well maintained. Enjoyed watching the wildlife. "
Cozy cabin minutes from Lake Cumberland with room for your boat.

A true guest favorite! Super clean! Close to everything!

10.0 out of 10, Exceptional, (8)
"Rebecca went out of her way to make us feel comfortable. The house is clean and well stocked. Close to the lake. Perfect getaway!"
The price is AED 437
AED 939 total
includes taxes & fees
30 Apr - 1 May
A true guest favorite! Super clean! Close to everything!

Serene Lakefront Retreat: Close to Marina, Park, & Downtown Charm

10.0 out of 10, Exceptional, (144)
"This place was perfect foe our family of 4. We absolutely loved it!!"
Serene Lakefront Retreat: Close to Marina, Park, & Downtown Charm

Newly renovated 3 bedroom cottage resort, pool, private boat dock

10.0 out of 10, Exceptional, (4)
"Very clean cabin. Great location. Check-in & check-out were super easy!"
Newly renovated 3 bedroom cottage resort, pool, private boat dock

Lake Cumberland Eclectic Retreat: Fire Pit + Views

10.0 out of 10, Exceptional, (14)
"We were very happy with the rental. Had everything we needed for our visit. It was very clean and the beds were comfortable. The check in process was smooth and the host was very communicative and accommodating. Great location Would stay here again. "
Lake Cumberland Eclectic Retreat: Fire Pit + Views

Renovated Cottage! Overlooks Dale Hollow!

10.0 out of 10, Exceptional, (61)
"Very nice place to stay! "
Renovated Cottage! Overlooks Dale Hollow!

Lake Daze, Blue Cottage <1mile to Jamestown Marina with space to trailer boat.

9.4 out of 10, Exceptional, (27)
"2nd year here; good location, very nice house, convenient for our needs. Drive is steep and can be slick, less able-bodied people may struggle with stairs to front or log steps to back door, interior is great. "
The price is AED 551
AED 1,275 total
includes taxes & fees
16 Apr - 17 Apr
Lake Daze, Blue Cottage <1mile to Jamestown Marina with space to trailer boat.

Lake Cumberland Lakeside Cabin

10.0 out of 10, Exceptional, (1)
"Quick stay, in town for a baseball tournament, but it was a great cabin in a great location! Will return and stay again!"
Lake Cumberland Lakeside Cabin

Cottage at Lake Cumberland; 6m walk to water at Clearwater public boat ramp

10.0 out of 10, Exceptional, (5)
"We stayed here for a fishing tournament. The house was very clean and the hosts quickly communicated when we inquired about adding an additional night. We would definitely stay here again on future Lake Cumberland trips!"
Cottage at Lake Cumberland; 6m walk to water at Clearwater public boat ramp

Country Cottage < 3 Mi to Dale Hollow Lake!

9.2 out of 10, Wonderful, (30)
"We enjoyed our stay in this very clean and up-to-date cottage!! The outside porch was not very clean but liked having the gate so our small dog could enjoy it with us while we had our morning coffee!! Found it extremely difficult to get our pontoon in to unload!! Gates are not wide enough to manage getting boats in and out easily! "
Country Cottage < 3 Mi to Dale Hollow Lake!

The Lakeside Escape Cumberland

10.0 out of 10, Exceptional, (5)
"The house has plenty of space and was very comfortable, we really enjoyed the screened porch. Michelle is very helpful and friendly!"
The Lakeside Escape Cumberland

Cozy cottage nestled in the woods bordering beautiful Lake Cumberland

8.4 out of 10, Very Good, (16)
"Enjoyed the stay. Property fit the decription. Only concern was the host never responded to any of our text. "
Cozy cottage nestled in the woods bordering beautiful Lake Cumberland

Newly remodeled, handicap accessible overlooking pool , play area

10.0 out of 10, Exceptional, (6)
"We just returned from a weekend stay. Property was just as described and location was perfect for our boating trip at Conley Bottom. Would stay here again!"
Newly remodeled, handicap accessible overlooking pool , play area
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.
Don't see what you're looking for?
See all available properties in Monticello
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Monticello

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

9.8 out of 10, Exceptional, (146)
"Quite place to kick back and relax, says you can fish there is a private deck at the home, but there is so many turtles in the pond they have ate all the fish. But not the owners fault, just a heads up on the private fishing dock. "
This charming cozy cottage has a private hot tub, deck for fishing.

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

10.0 out of 10, Exceptional, (105)
"This cabin was fantastic and had everything you could possibly want for a weekend getaway. Plenty of inside and outside activities and a wonderful place to get away and unwind. David & Valarie were great hosts, being as welcoming, and responsive as you could ask for. We very much enjoyed our stay and will hopefully look to be back!"
Lake Bluff Paradise on Lake Cumberland. Newly added game room and hot tub!

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!
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.