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

4.87 out of 5 average rating, 142 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.

Guest favourite

Tiny home in Monticello

4.95 out of 5 average rating, 219 reviews

*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.

Guest favourite

Home in Somerset

4.95 out of 5 average rating, 21 reviews

Make Waves@The Wet Spot

•Equipped eat-in kitchen stocked w/essentials •Cute + cozy lake decor • Gorgeous views from front porch grilling area + back deck w/hammock, seating + dining area • Private primary w/queen bed •Second bedroom w/twin + trundle beds •Full Bath includes sleek walk-in shower + modern amenities •Rustic farmhouse sink outside lower level is perfect for filleting up your catch •Open the basement garage door for extra entertaining space + laundry •Next to Omega Boat Ramp •25 min to Shops/Restaurants

Superhost

Cabin in Bronston

4.79 out of 5 average rating, 71 reviews

Lake front* New 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.

Guest favourite

Cabin in Burnside

4.93 out of 5 average rating, 355 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!

Guest favourite

Cottage in Somerset

4.94 out of 5 average rating, 224 reviews

Cozy Lakefront Cottage Getaway with Relaxing View

Fishing Creek Cottage overlooks Fishing Creek, a popular recreational area on Lake Cumberland and a major arm of the lake. Pulaski County Park and its beach and boat ramp can be seen across the lake. Boaters frequent the area to ski & tube, but are distant enough that noise isn't an issue. We are the last house at the end of a quiet street in a residential neighborhood, & so have relative privacy. The large deck and impressive view are frequently referenced in our guests' reviews.

Top Guest favourite

Guesthouse in Somerset

4.98 out of 5 average rating, 185 reviews

Elegant Modern Rustic Retreat w/ Hot Tub

A steel framed industrial warehouse converted into an upscale two bedroom rustic-chic living space located within 8 miles of beautiful Lake Cumberland and within 5 minutes of Downtown, Somerset. The city is yours to explore from your own private 2 bed, 1 bath modern rustic retreat. Picture comfy beds, full bathroom, a kitchen built for entertaining, all under a metal tin roof for those rainy days when you just want to curl up and relax.

Top Guest favourite

Cottage in Somerset

4.97 out of 5 average rating, 137 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!

Guest favourite

Cabin in Pulaski County

5 out of 5 average rating, 13 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, 42 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, 59 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