Vacation rentals in Monticello

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Top-rated vacation rentals in Monticello

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Guest favorite

Tiny home in Monticello

4.96 out of 5 average rating, 166 reviews

Adorable Tiny LakeView Cottage with kayaks!

Totally remodeled inside and out! We welcome your fur babies!! Adorable tiny house with a deck & bonfire pit overlooking a spectacular view of Otter Creek on Lake Cumberland. It is located in Monticello, Ky in a rural part of the area. It’s about 12 minutes to town. There is very close (driving distance) swimming access, kayaking, boating, boat ramps, fishing & marinas. Plus, your likely to see lots of wildlife. I have kayaks available for a small daily fee to rent. Pets allowed! $50/$75fee.

Jun 12 – 19

G$31,182 GYD per night

Guest favorite

Home in Monticello

4.91 out of 5 average rating, 127 reviews

Bluegrass Gables: Lake Cumberland Cottage

Relax in the forest is this amazing 4bd/2.5ba cottage. Only minutes to the Ramsey Point boat ramp, this is your base for your Lake Cumberland vacation. Bring your boat; ample parking onsite. Don't have a boat? No problem, Beaver Creek and Conley Bottom marinas are close by. House features modern amenities and a fully stocked kitchen. Enjoy the fireplace indoors or the firepit outdoors. Forest views and fresh air galore await you, especially from the hot tub! Absolutely no smoking inside or out.

Oct 31 – Nov 7

G$47,594 GYD per night

Guest favorite

Home in Oneida

4.98 out of 5 average rating, 151 reviews

Lazy Days Wilderness Cabin

Nature abounds, If hiking, horseback riding, four wheeling or just relaxing is what you crave, then this is the place for you! The property is 24 acres, sitting on the edge of Big South Fork National Park. The front yard is big enough for games. When you are through for the day and after enjoying the enclosed hot tub/pool inside, go outside and enjoy the fire pit area. Horses welcome, small pasture area, no barn. Owners live on property, always available. Pet fee $25. Welcome to our cabin.

Oct 2 – 9

G$29,950 GYD per night

Guest favorite

Cottage in Monticello

4.91 out of 5 average rating, 98 reviews

Clean and Cozy. Only 175 yards from the water.

Cabin House is located at beautiful Lake Cumberland near Monticello, KY. It is located approximately 175 yards from Old Fall Creek boat ramp. This is a Free boat ramp. No dock. If you should need to rent a boat, we are located close to the resorts at Conley Bottom and Beaver Creek. The cabin is known for being clean and comfortable. It is nestled among the trees next to land overseen by the Army Corp of Engineers. The area is always beautiful no matter what season. Come and Enjoy!!

Jan 23 – 30

G$23,792 GYD per night

Guest favorite

Cabin in Burnside

4.88 out of 5 average rating, 130 reviews

Cumberland Cabin Get Away

Come and get away! Relaxing cabin backing to the Daniel Boone National forest. Located in the Lake Cumberland Resort. This gated community offers swimming pools, tennis courts, easy boat ramp access, and security. Private setting provided in this cozy cabin is great for a couple and families. Private parking for 2 vehicles, fire pit, large covered back deck with LED lighting, and tons of movies and games for kids. Inside is decorated with antiques and has a great country farmhouse feel.

Dec 19 – 26

G$18,394 GYD per night

Guest favorite

Home in Monticello

5.0 out of 5 average rating, 68 reviews

Beautiful Farmhouse near Lake Cumberland

This beautiful farmhouse has lots of amenities, 3 bedrooms, 2 bath. Coffee bar, Nice backyard with fire pit, Weber gas grill, 6 camping chairs to sit by the cozy fire and corn hole and basketball goal for added fun! Full front porch and nice quiet back porch. Laundry soaps, shampoo, propane, laundry detergent etc included. 4 flat screen TV’s. Activities for kids. Swing set, Located 5 minutes to Beaver Creek Marina , 15 minutes to Conley Bottom and less that 5 minutes to city limits.

Jan 16 – 23

G$29,314 GYD per night

Guest favorite

Cottage in Monticello

5.0 out of 5 average rating, 65 reviews

The Cozy Cabell Cottage

It’s time for an adventure at our vacation rental, Cabell Cottage. With Lake Cumberland only 5 minutes away via the Cabell landing....really your boat is 5 minutes from being in the water; the cottage can be your base for all things fun on the lake (swimming, boating, and fishing). Did I CATCH your interest with fishing. However, if it’s a retreat you seek, the cottage is also for you as it sits in a quiet, very pretty, rural area of Wayne County, Kentucky, where 5 can sleep easily.

Sep 17 – 24

G$21,728 GYD per night

Guest favorite

Cabin in Burnside

4.93 out of 5 average rating, 298 reviews

Dixie Mtn. Hideout

Enjoy a breath taking Mountain view from your private log cabin as you drink your morning coffee. With memory foam beds you will wake refreshed and ready to enjoy all the Lake Cumberland area has to offer. Within 5 miles to General Burnside Sate Park and boat ramp and Burnside Marina. Your vacation home is only 10 miles from downtown Somerset, somernites car cruise capital! Boat parking available with turn around. Dixie Mtn. Hideout, when you're away from home, we welcome you home!

Feb 20 – 27

G$27,234 GYD per night

Guest favorite

Guest suite in Albany

4.98 out of 5 average rating, 202 reviews

Page's Legacy “Spring has sprung at the Lake”

All rooms have a view of the lake and the deck overlook Dale Hollow. We are a mile from Wolf River Boat Dock. The suite is downstairs with a private entrance. There are walking paths that encompasses 3 acres on the property. The private deck has a fire pit for chilly mornings to enjoy coffee or relaxing evening. There are some great day trips I have added to the "Host Guidebook" Click on "More about this location" and scroll to the bottom and click on "Show Host Guidebook"

Mar 20 – 27

G$29,335 GYD per night

Guest favorite

Home in Monticello

4.95 out of 5 average rating, 40 reviews

Vacationers delight at Conley Bottom

Don’t let the price fool you. We do Vacation right in this home. Less than a quarter mile from Conley Bottom Marina, this house is great for anyone looking to get away for the weekend. Your boat can be kept in the driveway, we have a golf cart you can rent during your stay, as well, to explore the area and drive down to the marina. Conley Bottom offers everything from the boat ramp, boat rentals, water sports, fishing. Five golf courses located within a half hour of the house

Oct 29 – Nov 5

G$24,692 GYD per night

Guest favorite

Cabin in Wayne County

4.93 out of 5 average rating, 44 reviews

Cozy cabin on private 18 acre farm near the lake.

Take it easy at this unique and tranquil cabin getaway on a farm all to yourself. Only ten minutes from both Conley Bottom and Burnside Island. Nestled amidst 18 acres of woods and a newly starting Christmas tree farm. Cozy by the fire pit, relax in the hammocks or take a stroll on several hiking trails. Within minutes you can enjoy great restaurants, entertainment, scenic lake views, a federal Wildlife Management Area, a 3D archery range and much more.

Jul 27 – Aug 3

G$27,357 GYD per night

Superhost

Cottage in Monticello

4.92 out of 5 average rating, 103 reviews

The Cozy Lake Cottage

This little cottage is in the woods and very private and just minutes away for Lake Cumberland. You are about 5 minutes away from Conley Bottom and there are also two closer docks that is a couple minutes away. You can take nature walks and see deer and other little animals or sit out by the campfire roasting marshmallows. We have a small drive that can fit two vehicles in and a driveway on the side that is big enough and long enough to park your boat in.

Jun 2 – 9

G$25,733 GYD per night