Holiday houses in Lake Cumberland

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Top-rated holiday rentals in Lake Cumberland

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Guest favourite

Home in Somerset

4.88 out of 5 average rating, 144 reviews

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.

Guest favourite

Home in Monticello

4.92 out of 5 average rating, 175 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.

Top Guest favourite

Home in Jamestown

5 out of 5 average rating, 21 reviews

Onyx House

Take a break and unwind at this peaceful oasis, surrounded by nature. Minutes to Lake Cumberland State Resort Park & Marina and Halcombs Landing Boat Ramp ‘Dam’-you’ll have easy access to the water. Outdoor seating with 3 decks, outdoor tv, and fire pit allows for great social entertainment and a perfect place to unwind. 2 private bedrooms downstairs (queen), with a 4 bed (full) loft upstairs. 2 bathrooms down stairs-one with walk-in shower, one with tub/shower. The kitchen is fully equipped.

Guest favourite

Cabin in Bronston

4.81 out of 5 average rating, 79 reviews

Lake front* Private dock * Firepit

This cozy a-frame is tucked into the lakeside neighborhood of Echo Point, on Cumberland’s picturesque South Fork. Fish off the dock, bring your paddle boards, or drop a boat in at the ramp around the corner. Relax on the back deck with rock wall views and lush green towering trees. Great for a couple's retreat or a small family getaway. Walk to water and dock via a rustic path and stairs (it’s a steep climb!) Stores & restaurants are 15 min drive. Dogs (2 max) welcome for additional fee.

Top Guest favourite

Cabin in Monticello

5 out of 5 average rating, 16 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!

Guest favourite

Tiny home in Monticello

4.95 out of 5 average rating, 220 reviews

*Tiny LakeView Cottage* Pets welcome! Kayaks

We welcome your fur babies!! Kayaks available! Ice maker! Coffee pot w/coffee & creamer! Adorable, cozy 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. Kayak rental is available for $25. per day/per kayak. Pet fee $50/$75 per stay.

Top Guest favourite

Home in Russell Springs

5 out of 5 average rating, 27 reviews

Welcome to your Dream Lake Home

Welcome to a place to forget your cares. This stylish home is perfect for family or group trips. Stunning lake views year round, 5 bedrooms/3 baths, games for kids or adults including foosball and ping-pong, a grilling area and full kitchen to prepare your catch of the day, a cozy electric fireplace, and a boat ramp less than 1 mile for easy access to all your water activites. Come see why they say "Lake life is the best life!"

Top Guest favourite

Home in Wayne County

4.9 out of 5 average rating, 20 reviews

Lake House "Dar Bida" Monticello

Forget your worries in this spacious and serene space. You will enjoy the silence and magnificent view on Lake Cumberland. "Dar Bida" is the ultimate place to relax and enjoy time with your family or friends. Lake Cumberland offers plenty of possibilities for outdoor activities such as boating and fishing. Two boat ramps are within 5 miles and boats can be stored at a dedicated boat storage area within the gated residence.

Top Guest favourite

Cottage in Somerset

4.97 out of 5 average rating, 138 reviews

Cozy Lakehouse with a View

Imagine waking up in the morning to the birds chirping in the woods surrounding the cabin, fixing a cup of coffee, and relaxing on the deck that provides one of the best views you will ever experience on Lake Cumberland. This cabin is perfect for a romantic getaway, or a quiet retreat with the family. Simply put, this cabin offers memories that you will cherish for a lifetime and will talk about for years to come!

Superhost

Cabin in Pulaski County

4.94 out of 5 average rating, 17 reviews

New Lakeview Couples Getaway | Romantic & Private

The majority of the home is lined in cedar. The main level holds a full size bathroom with a washer and dryer, a bedroom with a queen size bed, kitchen, and living area that has plenty of floor space for you to bring an additional air mattress. Deck access is off the living area. A set of stairs takes you to the loft that holds a king bed and has access to a small Juliet deck that faces the front of the property.

Top Guest favourite

Home in Jamestown

5 out of 5 average rating, 50 reviews

Midnight Pearl

A mountain modern luxurious home designed for a couples' getaway features sleek, contemporary architecture offering stunning mountain views. Inside, a spacious living room boasts a cozy, modern fireplace, while outside, multiple fire pits create intimate, warm spaces under the stars. The interior is adorned with high-end finishes, blending natural wood and stone elements for a serene, upscale retreat.

Guest favourite

Home in Somerset

4.88 out of 5 average rating, 69 reviews

Coffee with the Squirrels

New chalet only 5 minutes to city of Somerset and 5 minutes to Lake Cumberland! Cozy 1 king size bedroom with custom features throughout. Walk out on your master suite deck and have coffee with nature! Full size bathroom w custom tile. Back deck that overlooks woods and wildlife. Sometimes there is a neighbor who has a dog that barks a couple housss down, I’m sorry if it does, doesn’t happen often