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Search Monticello Cottage Rentals from CA $113

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Check prices for these dates

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Aug 22 - Aug 24
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Aug 29 - Aug 31
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Sep 12 - Sep 14
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Oct 10 - Oct 12

Browse Select Monticello Cottages

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 CA $198
CA $493 total
includes taxes & fees
Aug 21 - Aug 22
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 CA $138
CA $319 total
includes taxes & fees
Sep 1 - Sep 2
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 CA $220
CA $539 total
includes taxes & fees
Aug 21 - Aug 22
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 CA $274
CA $603 total
includes taxes & fees
Aug 17 - Aug 18
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 CA $191
CA $381 total
includes taxes & fees
Aug 26 - Aug 27
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 CA $248
CA $521 total
includes taxes & fees
Aug 14 - Aug 15
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 CA $155
CA $338 total
includes taxes & fees
Aug 14 - Aug 15
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 CA $558
CA $1,007 total
includes taxes & fees
Aug 14 - Aug 15
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 CA $113
CA $269 total
includes taxes & fees
Aug 14 - Aug 15
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

Dale Hollow Lake State Resort Park

Dale Hollow Lake State Resort Park

10/10 Excellent
"This park appears to have it all. Plenty of activities and the accommodations were great. The rooms were very clean and they were quiet. Staff was very friendly and helpful. "
Jeff 2-night trip
Posted 2 days ago
Dale Hollow Lake State Resort Park