Vacation rentals 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.

Lake Cumberland Resort Getaway

Charming private cottage in a gated Community at Lake Cumberland Resort, this 3-level home sits on 2 acres inside in the Daniel Boone National Forest & has fantastic reviews. Watch the sunrise from the front porch swing & sunsets from the the hot tub patio around the outdoor fire place. Gather around a campfire pit under the stars, or hike over a hundred miles of trails that literally start in your back yard. Active security patrols, three swimming pools, boat ramp, boat dock & tennis courts.

Blackbeard’s Lakefront Bungalow

Blackbeard’s Bungalow is located in beautiful Somerset overlooking Pitmann creek on Lake Cumberland. Enjoy the amazing year round lake views. Three large bedrooms, two full bathrooms, great room, dining room, open kitchen , screened in porch, and double decks are all yours for rest and relaxation or quality time with those you care about. Less than 10 miles to Pulaski park, Lee’s ford marina, and Burnside marina, this is the perfect location close to all conveniences but the perfect getaway.

Cozy Lakehouse – ZERO Cleaning Fee, Pet Friendly!

Discover an unforgettable escape at our breathtaking Burnside vacation home, where every moment becomes a cherished memory. • Nestled on the shores of Lake Cumberland, offering breathtaking lake views. • Luxurious amenities: Spacious 4BR, beautiful deck, screened-in sunroom with a view! • Endless entertainment: Fire pit & fully equipped game room for all ages. • Relaxation awaits: with a serene patio deck & modern comforts. • Ideal for large groups: Accommodates 14 guests, pet-friendly.

Lake Top Cabin #10

Completely remodeled lake view home at top of Lake Cumberland Marina. A spacious covered porch with a swing for those summer days and nights. 2 picnic tables and a grill for outdoor grilling days. A large deck with stunning views of the lake. Perfect for enjoying your morning coffee or evening wine after a great day on the lake. Perfect for large families or groups. Sleeps 10. Pets are welcome. Backyard is spacious for kids to play. Plenty of parking for your boats and vehicles. .

The Enchanted Hideaway /Pet Friendly with Hot Tub!

Come relax at the Enchanted Hideaway Cabin just minutes from beautiful Lake Cumberland within the gated Lake Cumberland Resort. This 2 BR 2BA cabin offers much to love including open concept kitchen, dining, and living room area, washer and dryer, screened-in porches, grill, fire pit and much more! And you will love the private hot tub on the back porch! There are 3 community swimming pools in the resort with one only a short walk from the cabin. Book your perfect get-a-way today!

Lowe Tide Log Cabin

Location, location! This newly remodeled log cabin sits overlooking Burnside island and around the corner from Burnside marina! Minutes from three boat ramps. Parking for 3 plus vehicles and a boat. Cabin offers master with king bed/bath, loft with a queen bed, family room with sleeper sofa, and power love seat, nice kitchen and second full bath with tub/shower. Cabin is located on a quiet dead end street and is surrounded by trees and is close so several restaurants and stores.

Lake Cumberland Luxury #2~ Lake views and hot tub.

One of Airbnb’s favorites, under new ownership! Same home same luxury~ Come enjoy the best that Lake Cumberland has to offer. This beautiful, spacious, and private home offers one of the best views of Lake Cumberland you will see. With 5 bedrooms and 2.5 bathrooms you will have plenty of space to sleep up to 10 guests—making it a perfect trip for families and friends. There is a hot tub, pool table, fire pit, cornhole and tons of games to take your stay to the next level.

Lucky Lake Haven- Hot Tub, Peaceful Retreat

Beautifully decorated, Super Clean Home with all the Extras. Two Bedrooms both are King beds with fresh linens. Huge Deck nestled in the trees. Wonderful for bird watching or playing corn hole, or soaking up some sunshine. Lovely Sunroom, with space to eat, read, relax and enjoy your trip. Board games, books, plants. Large kitchen open to Dining and Living room. All the essentials that you might need are provided. A Private Hot Tub, and a Fire Pit.