Vacation rentals in Monticello

4.87 out of 5 average rating, 142 reviews

Home in Somerset

Lakeview Blue

You will not find a better view of Lake Cumberland! Newly renovated 2022!! Previously our family home, we cherish this property. We ask anyone renting to respect the neighbors and home as we have. The Lakeview Blue House is within walking distance of Lake Cumberland, several restaurants, gas stations and a liquor store. There is a seasonally open public boat ramp directly over the hill from the home and many others including Waitsboro, Burnside Marina and Burnside Island State Park/ ramp nearby.

4.92 out of 5 average rating, 175 reviews

Home in Monticello

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.

4.95 out of 5 average rating, 219 reviews

Tiny home in Monticello

*Tiny LakeView Cottage* Pets welcome! Kayaks

We welcome your fur babies!! ATV trail to lake! Ice maker! Coffee! Adorable tiny house with two decks & bonfire pit overlooking 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. On a dead end street, so very peaceful. Also has an ATV trail to lake!! Kayak rental is available for $25. per day/per kayak. Pet fee $50/$75 per stay.

4.97 out of 5 average rating, 61 reviews

'Top of the Hill'- Cozy Retreat with Hot Tub!

Take a break and unwind at this peaceful, recently renovated cottage nestled under large shady trees. Located within one mile of two public boat ramps for launching your boat, fishing, or swimming. Five miles from Conley Bottom. The house features a hot tub with room for up to four people. There is room to park one or more smaller boats (23 ft or less). Two bedrooms, one full-size sleeper sofa, one bathroom with shower only, a large deck, outdoor wood-burning fire pit, and gas grill.

5 out of 5 average rating, 106 reviews

Home in Bronston

Lake Cumberland Getaway near Conley & Burnside

Welcome to our countryside getaway nestled on almost 5 acres within 5-20 miles of Burnside, Lee's Ford, and Conley Bottom Marinas. Enjoy the day on Lake Cumberland. Come back to relax, eat, drink & be merry. Gather around the outside barbecue area and fire pit or snuggle up inside next to the fireplace, playing games or watching a movie. Whether you are on a couple's retreat, fishing buddy's getaway, or family vacation - the house and outdoor area provide plenty of room to relax and enjoy.

4.94 out of 5 average rating, 109 reviews

Cabin in Jamestown

River Loft Cabin w Free Kayaks

Free kayaks at this remote log cabin on the river in the Tennessee Highlands! Kayaks include one double sit-on-top kayak, one single Pescador kayak, and one single sit-in kayak. Our off-the-grid cabin overlooks the East Fork Obey River (Dale Hollow Lake), and the scenic Tennessee Highlands. Stroll down to the water to fish or launch your boat from the nearby ramp on Riverton Road, just one street over. End the day by the outdoor fireplace, or relax on one of the two porches to stargaze.

5 out of 5 average rating, 13 reviews

Lake Cumberland Cottagey Cabin! 9-min to Marina!

Serenity, tranquility & an inner peace is what you'll feel upon entering! Our 3-level, 4BR, 2BA cottagey Cabin accommodates 8 guests. It boasts a seasonal view of CONLEY BOTTOM MARINA from its secluded, private, wooded lot! Inside, the warmth of natural woods will envelop you! And, the chef in your group will love the adorable kitchen equipped with every imaginable gadget, spice & cooking basic! Appointed in Cottagecore design, SERENITY RIDGE is the perfect blend between yesterday and today!

4.94 out of 5 average rating, 65 reviews

Tent in Monticello

Enchanting Glamping Tent on Lake Cumberland

Named for a favorite Willy Porter song, "Moonbeam" is a 12'x14' safari tent on a wooden platform with a roof. Listen to tree frogs while drifting off to sleep on a queen size memory foam bed with soft, dreamy linens. The tent features power, lamps, chairs, and a desk. Outside, enjoy a private fire pit or sit a spell on rocking chairs on the back deck. Our Community Shelter, with a fridge, sink, and coffee maker, and our Bath House with flush toilets and hot showers are a short walk away.

5 out of 5 average rating, 19 reviews

Home in Monticello

Home 0.2 miles from boat ramp with game room

Relax and get away with your whole family at our newly remodeled lake home! We are located 0.2 miles from the nearest Lake Cumberland boat ramp. We have plenty of driveway space to park your boat. We offer an adorable master bedroom with your own private bathroom. Our garage is filled with indoor and outdoor games for all ages. The area is known for its welcoming atmosphere and small community hospitality. We are located 12 miles from Safe Harbor and 19 miles from Conley Bottom Resort.

4.91 out of 5 average rating, 118 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!!

4.94 out of 5 average rating, 66 reviews

Cozy Cabin - Lake Cumberland w/ Hot Tub

Our cozy cabin is located on Lake Cumberland in Monticello close to Somerset and two great marinas, Conley Bottom being our favorite! We have partial lake views in the fall, winter and spring and a hot tub on the deck to enjoy the views, along with the fire pit below. We have 2 bedrooms, one bathroom and a pull out couch. The large wrap around deck is perfect for playing games and hanging out. Please note there is no lake access from the property. Also - Please note stairs to access.

5 out of 5 average rating, 91 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.

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Monticello vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Monticello

4.92 out of 5 average rating, 13 reviews

Home in Albany

Elisi's Cozy Nook 3.2 mile from Marina Rowena.

NatalieRating, 5 stars3 weeks ago

Great place to stay to get away. Country setting with great views. Very quiet and relaxing place. The house was perfect for us. Kitchen is fully stocked with everything you would need. Very close to Rowena Marina. We will definitely be back to stay.

4.92 out of 5 average rating, 152 reviews

Cabin in Bronston

Cabin on lake Cumberland

BrendaRating, 5 stars2 weeks ago

My sister, niece and I stayed at the cabin. It was cozy and comfortable. I would stay again if I was in the area. It is convenient to stores and restaurants.

5 out of 5 average rating, 11 reviews

Luke’s Porch

JenniferRating, 5 stars9 months ago

We had a very peaceful weekend. We felt right at home. We needed peace and found it. It was clean. We were able to cook as we normally do. The air conditioner was the hard to understand but we managed to use the fans he provided and were comfortable. The water was always nice and hot to shower. It was close to gas stations and restaurants and grocery stores. We made a trip to one of the falls and enjoyed the drive. There is internet. But the most important thing is aspect was peaceful and allowing our dog to come along and feel welcome.

4.89 out of 5 average rating, 9 reviews

Home in Monticello

Freshly remodeled cottage near the lake.

MichaelRating, 5 stars5 months ago

Kevin was a great host. He is very responsive and communicates well. The cottage was clean. It was in a quiet and peaceful location. I really enjoyed our stay and hopefully get to stay there again in the future.

5 out of 5 average rating, 8 reviews

Lakeside Lodge Cabin

BrettRating, 5 stars3 days ago

Very quiet and peaceful location. Close to the water. Cabin had everything we needed. Would definitely stay again.

4.93 out of 5 average rating, 112 reviews

The Cozy Lake Cottage

JoshuaRating, 5 stars1 month ago

This place has a very cozy with and peaceful location. Highly recommended😊

Superhost

Home in Jamestown

5 out of 5 average rating, 4 reviews

Honeymoon Luxery Escape

JordanRating, 5 starstoday

Finns BnB was the most wonderful home to spend our first anniversary as husband and wife. The seclusion was truly serene. The home was filled with amenities that made our trip effortless. Every detail was so thought out that we were left with nothing to do but enjoy our stay. The local recommendations Sawbriar Brewery and Highland Manor Winery, were both stunning and worth every penny. We chose to extend our stay by a night which was quickly accepted by the host. We loved our stay so much we are already planning our return.