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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Cottages in Monticello and around

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

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

9.6 out of 10, Exceptional, (226)
"It rained a lot, but we still had a great time. The property was just as advertised with an amazing view!"
Lake Front Home with community boat ramp. Private, close to marinas and town.
Above J’town Marina, LCKY. boat parking. 3 full baths. pool table. pet friendly.
Terrace/patio

Above J’town Marina, LCKY. boat parking. 3 full baths. pool table. pet friendly.

10.0 out of 10, Exceptional, (179)
"This is a phenomenal property to stay at. Plenty of space and comfortable.beds. I loved the pool table downstairs and we used the fire pit to make s'mores.Jamestown Marina is just a couple of minutes away which was great for us.We've already booked again in September."
The price is €315
includes taxes & fees
18 Aug - 19 Aug
Above J’town Marina, LCKY. boat parking. 3 full baths. pool table. pet friendly.
Serene Lakefront Retreat: Close to Marina, Park, & Downtown Charm
Outdoor dining

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

10.0 out of 10, Exceptional, (147)
"This place was perfect foe our family of 4. We absolutely loved it!!"
The price is €201
includes taxes & fees
7 Sept - 8 Sept
Serene Lakefront Retreat: Close to Marina, Park, & Downtown Charm
Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!
Exterior

Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!

10.0 out of 10, Exceptional, (19)
"Absolutely loved our short time in this home! Very clean and well furnished! We hope to stay again soon!"
The price is €343
includes taxes & fees
4 Sept - 5 Sept
Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!
NEW!The Overlook @ Harbor Springs-2 miles from Jtown Marina! Lake Views+Parking
Property grounds

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

10.0 out of 10, Exceptional, (47)
"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
Harbor Hideway is a cozy, romantic gem minutes away from Jamestown Marina!
Exterior

Harbor Hideway is a cozy, romantic gem minutes away from Jamestown Marina!

10.0 out of 10, Exceptional, (11)
"Great experience, very cute home. Would love to visit again! "
The price is €387
includes taxes & fees
15 Aug - 16 Aug
Harbor Hideway is a cozy, romantic gem minutes away from Jamestown Marina!
Serene Cottage on 18 Acres Close to Lake Cumberland
Exterior

Serene Cottage on 18 Acres Close to Lake Cumberland

10.0 out of 10, Exceptional, (1)
"Our whole stay was effortless! From communication with Jamie, property location, access and matching expectations as advertised. What a delight to, for once, not be unpleasantly surprised by VRBO. We will definitely consider this place in the future. "
The price is €243
includes taxes & fees
28 Aug - 29 Aug
Serene Cottage on 18 Acres Close to Lake Cumberland
LAKE CUMBERLAND, FENCED YARD, FIRE PIT, HOT TUB, 100 meg internet, FIREPLACE
Outdoor spa tub

LAKE CUMBERLAND, FENCED YARD, FIRE PIT, HOT TUB, 100 meg internet, FIREPLACE

10.0 out of 10, Exceptional, (250)
"Great place for all Cumberland fun. Fenced yard is a plus "
LAKE CUMBERLAND, FENCED YARD, FIRE PIT, HOT TUB, 100 meg internet, FIREPLACE
Walk to Dale Hollow Lake: Updated Cottage w/ Deck!
Property grounds

Walk to Dale Hollow Lake: Updated Cottage w/ Deck!

8.8 out of 10, Excellent, (11)
"Nice house. Convenient location. Will definitely stay again."
Walk to Dale Hollow Lake: Updated Cottage w/ Deck!
Renovated Cottage! Overlooks Dale Hollow!
Exterior

Renovated Cottage! Overlooks Dale Hollow!

10.0 out of 10, Exceptional, (66)
"Very nice place to stay! "
Renovated Cottage! Overlooks Dale Hollow!
Country Cottage < 3 Mi to Dale Hollow Lake!
Exterior

Country Cottage < 3 Mi to Dale Hollow Lake!

9.2 out of 10, Wonderful, (33)
"great spot- easy and convenient. Having two bathrooms was the best and everything was clean upon arrival."
Country Cottage < 3 Mi to Dale Hollow Lake!
Sunny Daze Cottage 3 bedroom covered deck resort boat dock pool firepit arcade
Exterior

Sunny Daze Cottage 3 bedroom covered deck resort boat dock pool firepit arcade

10.0 out of 10, Exceptional, (11)
"Very clean cabin. Great location. Check-in & check-out were super easy!"
The price is €332
includes taxes & fees
17 Aug - 18 Aug
Sunny Daze Cottage 3 bedroom covered deck resort boat dock pool firepit arcade
Guest Favorite! Super Clean! Close to Everything!
Terrace/patio

Guest Favorite! Super Clean! Close to Everything!

10.0 out of 10, Exceptional, (8)
"Very clean and all amenities set up perfectly for our stay. Made a perfect middle ground for visiting mammoth caves and cumberland falls."
The price is €217
includes taxes & fees
17 Aug - 18 Aug
Guest Favorite! Super Clean! Close to Everything!
This charming cozy cottage has a private hot tub, deck for fishing.
Terrace/patio

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

9.8 out of 10, Exceptional, (151)
"This was our anniversary, the place was well maintained and the manager was nice and accommodating "
This charming cozy cottage has a private hot tub, deck for fishing.
Restful Rustic Farmhouse on Lake Cumberland
Terrace/patio

Restful Rustic Farmhouse on Lake Cumberland

9.4 out of 10, Exceptional, (10)
"This house and location was perfect for 8 adults and 2 children. Tremendous room to spread out and find some peace, huge wrap around porch and all the essentials in the kitchen. Located just a few miles from the Jamestown Marina. Joe went out of his way to communicate, even coordinating the pick up of a few things that we left behind. Highly recommend!"
The price is €635
includes taxes & fees
17 Aug - 18 Aug
Restful Rustic Farmhouse on Lake Cumberland
EASY CHECKOUT INSTRUCTIONS Luxury Linens and Towels,Hybrid pillow top mattress
Exterior

EASY CHECKOUT INSTRUCTIONS Luxury Linens and Towels,Hybrid pillow top mattress

10.0 out of 10, Exceptional, (1)
"Stayed here 2 nights in order to visit Cumberland Falls which was only 30 minutes away. We had a very warm welcome and comfortable stay. Would definitely stay here again. "
The price is €171
includes taxes & fees
15 Aug - 16 Aug
EASY CHECKOUT INSTRUCTIONS Luxury Linens and Towels,Hybrid pillow top mattress
Cottage at Lake Cumberland; 6m walk to water at Clearwater public boat ramp
Property grounds

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

10.0 out of 10, Exceptional, (5)
"We had a lovely stay at Jo’s Cottage. We enjoyed grilling out and hanging out on the deck. The cottage was very clean and well appointed. The location was quiet and conveniently located, just a short walk to the boat ramp."
Cottage at Lake Cumberland; 6m walk to water at Clearwater public boat ramp
Pet-Friendly Somerset Cottage Near Boat Ramps!
Exterior

Pet-Friendly Somerset Cottage Near Boat Ramps!

8.4 out of 10, Very good, (6)
"Will be back in 2025. Gotta find an area to swim and bank fish. House was cute and fully loaded. All you need is clothes and food.Nice the firewood was there. Campground hostswere really mice "
Pet-Friendly Somerset Cottage Near Boat Ramps!
Family-friendly Lake Cumberland Vacation Rental
Interior

Family-friendly Lake Cumberland Vacation Rental

3.0 star property
8.6 out of 10, Excellent, (4)
"It was a beautiful Home! We enjoyed our stay very much. The owners were kind and responded quickly with any questions we may have had. Definitely plan on returning! "
Family-friendly Lake Cumberland Vacation Rental
Burnside Vacation Rental, Walk to Lake Cumberland!
House (4 Bedrooms) | Interior

Burnside Vacation Rental, Walk to Lake Cumberland!

3.0 star property
Burnside Vacation Rental, Walk to Lake Cumberland!
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

Cumberland Falls State Resort Park

Cumberland Falls State Resort Park

10/10 Excellent
"The continental breakfast was my only poor rating 7 types of cereal "
Susan 1-night trip
Posted 2 days ago
Cumberland Falls State Resort Park

Frequently asked questions

How much do cottages in Monticello cost?
Cottages in Monticello range between €171 and €635 per night. These retreats offer a chance to get in tune with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in Monticello with Expedia?
Reserving a cottage in Monticello is as easy as entering your travel dates and selecting your ideal place for a getaway in nature. From high-end retreats to budget-friendly properties and cottages that come with perks like a pool, Expedia has something for all styles. As for unbeatable deals? We've have them as well!
How can I find cheap cottages in Monticello?
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