Holiday houses in Monticello

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Top-rated holiday rentals in Monticello

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Guest favourite

Cabin in Monticello

4.95 out of 5 average rating, 20 reviews

Lakeside Lodge Cabin

Welcome to the Lakeside Lodge near Lake Cumberland, Kentucky, surrounded by stunning natural beauty and a wealth of attractions. Imagine waking up to the sounds of nature, spending your days exploring the lake or hiking the forest trails, and returning to a warm fire accommodations. This cozy cabin is perfect for small groups or families looking for an easy access to Lake Cumberland. Take a 5 - 10 min walk down a neighborhood road to access the small beach by the lake, as well as the boat ramp

Top Guest favourite

Home in Bronston

4.99 out of 5 average rating, 127 reviews

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.

Guest favourite

Tiny home in Monticello

4.95 out of 5 average rating, 231 reviews

Tiny LakeView Cottage~Pets! 1 nights available

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.

Guest favourite

Home in Somerset

4.91 out of 5 average rating, 172 reviews

Tandy Tiny House

Welcome to Tandy Tinyhouse! This Adorable 1Br is Brand New and has everything you need! Very Modern Kitchen w/tiled backsplash, Microwave, Keurig, Refrigerator, Range and Granite Counters. LTV Flooring and 10ft Ceilings throughout. En-suite features a Barn door and Tiled Shower. Washer/Dryer Combo just off of the Kitchen Area. Amazing location 3 minutes to Downtown Somerset and 10 minutes to Lees Ford Marina. You will want to stay here again and again! Please leave mini split 68 or above

Top Guest favourite

Home in Monticello

5 out of 5 average rating, 14 reviews

Cozy Countryside Cottage at Lake Cumberland

Rejuvenate at our family home, 2.5 miles from Beaver Creek marina on Lake Cumberland, in Monticello, KY. Nine generations of our family have enjoyed this property. Parts of the original cabin are incorporated into the current structure. Three outdoor seating areas, a fire pit, games and a wooded area let you enjoy the outdoors. The interior sleeps up to 8 and has everything you need! The home has been lovingly cared for and enjoyed by our family. We hope to share its gifts to you!

Top Guest favourite

Cabin in Monticello

5 out of 5 average rating, 21 reviews

Cottagey Cabin ~ Secluded & Amazing Fall Foliage!

Serenity, tranquility & an inner peace is what you'll feel upon entering! Our 3-level, 4BR, 2BA cottagey Cabin accommodates 8 guests and boasts a seasonal view of CONLEY BOTTOM MARINA from its secluded, private, wooded lot! Inside, the warmth of natural woods will envelop you! 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!

Top Guest favourite

Home in Monticello

4.99 out of 5 average rating, 88 reviews

< 1/8 Mile to Ramp, Two King Suites, Spa, Fire Pit

Escape to Barndo Bliss, a newly built 4bd/3.5ba retreat nestled in Lake Cumberland's serene forests, just 0.8 miles from Ramsey’s Point boat ramp! Perfect for families and friends, this home features TWO luxurious King En-suites. No boat? No problem! Nearby Beaver Creek Marina offers rentals. Enjoy evenings by the large firepit surrounded by nature, perfect for s'mores, and unwind in the luxurious spa. Experience the tranquility of Lake Cumberland—book your stay at Barndo Bliss today!

Top Guest favourite

Cottage in Monticello

5 out of 5 average rating, 103 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.

Top Guest favourite

Cottage in Monticello

4.97 out of 5 average rating, 70 reviews

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

Take a break and unwind at this peaceful 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 walk-in shower, a large shady deck, outdoor wood-burning fire pit, and gas grill.

Guest favourite

Cabin in Monticello

4.94 out of 5 average rating, 18 reviews

D&D Cabin at Lake Cumberland *Pets Welcome*

Our cabin is a cozy place to relax and enjoy with the whole family. It is centrally located in Monticello, Ky. There is 2 parking areas to accommodate guest and boat parking. We are 5 minutes from Walmart and Black Stallion Steakhouse. Conley Bottom and Beaver Creek Resort is within 15 minutes. Nearby are multiple docks for fishing. We have an outdoor grill and picnic table with privacy fence. Marina Rowena is 28 minutes away. As well as Safe Harbor Marina is 25 minutes from here.

Superhost

Home in Monticello

5 out of 5 average rating, 3 reviews

Bluegrass Fables @ Beaver Creek

At Bluegrass Fables, your story begins with breathtaking vistas of Lake Cumberland. Perched on a mountain above Beaver Creek's confluence with the main channel, this luxury retreat offers a modern lodge aesthetic and a million-dollar view. Immerse yourself in nature’s beauty, luxury finishes, and a setting that feels like the start of an unforgettable tale. Whether for friendship, family, or solitude, this is more than just a getaway; it’s the next chapter of your story.

Guest favourite

Apartment in Burnside

4.83 out of 5 average rating, 12 reviews

The Retro Suite (500B) Fun, Lake, Golf carts, Food

Welcome to “Retro Suite” – Your 1950s-Inspired Lakeside Getaway Step Back in Time with the Retro Suite Embark on a journey to the “good ol’ days” with our Retro Suite, a whimsical 1950s-inspired haven where bold, playful colors bring back the charm of a bygone era. From the moment you arrive, you’ll feel the nostalgia with encounters of iconic American figures and a vintage record player spinning tunes from Elvis Presley and The Beatles.