Holiday rentals in Grayson County

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Top-rated holiday rentals in Grayson County

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Guest favourite
A welcoming interior showcases a chalkboard greeting, with a cozy seating area featuring a leather sofa. Warm lighting fixtures hang from the ceiling, illuminating wooden accents and the open layout connecting living spaces. A colorful area rug adds texture to the floor.
Home in Millwood
4.94 out of 5 average rating, 144 reviews

The Shug Shack -close to Mammoth Cave & Beech Bend

The Shug Shack is a Illinois Central Railroad section house built in 1905. Loving restored to capture the feel of an old railroad depot it is on an ACTIVE P&L railroad route, very close to house PLEASE BE AWARE! Many of the original features and materials have been reused while being updated with modern upscale amenities. Well-stocked kitchen & gas fireplace. Has one master bedroom & one bath with two oversize leather chairs that make twin beds. Cozy with lots of charm, it feels like home!

Top guest favourite
A charming single-level house features a blue metal roof and white siding. The front porch is furnished with rocking chairs and a welcoming entrance. A spacious lawn surrounds the home, with visible trees and utility poles in the background.
Home in Leitchfield
4.99 out of 5 average rating, 141 reviews

Nana and Pa’s Place

At Nana and Pa’s Place we want you to feel right at home. Great place to stop & rest during your travels, or stay a few days and enjoy the slow pace of a small community. Comfy beds. Sofa bed has memory foam topper. Coloring books, toys, board/card games, light reading material. Fire pit & charcoal grill, wood & charcoal provided. Fully equipped kitchen and utility. Just 45 min. to Elizabethtown or Bowling Green. 60 min. to Louisville or Owensboro. 10min. to Leitchfield Restaurants and HOSPITAL.

Guest favourite
A spacious living area features a comfortable sectional sofa accented by a plaid throw. Two black chairs are positioned beside a round wooden table. The kitchen showcases modern cabinetry and a cozy dining setup, with large windows allowing natural light.
Bungalow in Leitchfield
4.95 out of 5 average rating, 128 reviews

Cozy cottage 5 min to Nolin Lake

Welcome to the "Buffalo Bungalow"! Fully renovated, gorgeous 2 bedroom cottage w/ included camper (3rd bedroom). Patio, hot tub, Blackstone griddle, gas grill, fire pit. Cowboy style camper w/ bar, video game & poker table. Master bedroom features king size bed, 2nd bedroom a queen bed, camper w queen. Luxury linens. 3 smart TV's w/ Netflix. Cozy living room, kitchen w/ all you need to cook & a frig. 5 min to Nolin Lake & 20 min to Mammoth Cave. Plenty of space for parking your lake toys.

Superhost
Home in Cub Run
4.81 out of 5 average rating, 118 reviews

The Brin @ Nolin - 3 Bdr. w/King Suite - Boat Ramp

You'll Feel Right at Home at This Charming 3 Bedroom Cottage @ Nolin Lake. Master Suite w/ King-Size Bed & Living Area. Close to Mammoth Cave (40 min) & Nolin Lake State Park (5 min). Only 1/4 mi to Boat Ramp Where You Can Launch Your Boat, Swim & Fish. The Outdoor Space Is Secluded and Surrounded by Woods. The Pergola Is the Perfect Spot to Relax and Take In the Sounds of Nature. Freestanding Immersion Tub & Double Vanity Glass Bowl Sinks. *Fast Wi-Fi *Grill *Fire Pit *Smart TV's w/ Roku

Top guest favourite
A cozy corner of the studio features a mustard yellow couch adorned with a patterned pillow, positioned against a textured wall. Framed mirrors and decorative wall art are arranged artfully above, while a lamp adds a warm glow beside a small, round table.
Flat in Leitchfield
4.97 out of 5 average rating, 30 reviews

The Chassedi / Historic Downtown Hotel / Studio

Welcome to The Chassedi! This newly renovated 1-King bedroom / 1-bathroom studio creates a unique and fun environment. You will enjoy lots of natural light with a spacious open concept for the living, kitchen, dining area and bedroom. With a fully equipped kitchenette, you can make a quick meal or enjoy the easy access to the city's shopping, dining, & entertainment venues. You will be comfortable in this fun and unique apartment inside the Historic Alexander Hotel. #kentucky #leitchfield

Guest favourite
The exterior of a charming two-story building features a white façade, complemented by brick accents. Large windows allow natural light to enter, while a welcoming porch showcases seating arrangements. A clear blue sky frames the structure, emphasizing its inviting presence in a casual neighborhood setting.
Flat in Leitchfield
4.86 out of 5 average rating, 70 reviews

Charm At 401

Charming 2 bedroom, 1 bath, 2nd floor apartment in the heart of Leitchfield. Fully furnished and tastefully decorated. Minutes from shopping, dining, and a short drive to both Nolin and Rough River Lake. Luxury Pottery Barn linens and high end furniture throughout the unit. The unit is above 2 office spaces. We try to work from home when hosting, but please understand you may see us during your stay. We always alert the guest before entry. The offices are locked off from the main entrance.

Superhost
A spacious outdoor deck features a circular arrangement of red Adirondack chairs surrounding a fire pit. A shaded dining area with a black umbrella is visible alongside a seating area. The cabin's exterior, clad in dark wood, is set within a serene forest backdrop.
Cabin in Peonia
4.84 out of 5 average rating, 165 reviews

Nolin Cabin Experience w/ Hot Tub

Welcome to the Ponderosa! This unique lake getaway includes a quaint Amish built cabin , Kitchen house, and 2 bed bunk house. All connect to a HUGE wrap around deck built to entertain and relax on. Small, simple, and set up for a relaxing get away with the family! This property has a wide walking trail down to the redline. Private gated entry and ample parking for many cars/trailers. Boat rentals and rental docks are available at nearby Ponderosa Marina and Wax Marina. NEW HOT TUB!

Guest favourite
A modern lake house is depicted, showcasing a two-story exterior with gray siding and stone accents. A welcoming porch features potted plants and seating, surrounded by lush green grass and mature trees, creating a serene outdoor environment.
Home in Leitchfield
5 out of 5 average rating, 25 reviews

Lake House on Rough River! Decorated for Christmas

Relax at this new custom lake house with family and friends! It is located in Holiday Rough Subdivision on Rough River Lake approximately 10 minutes from Leitchfield, KY. In the evenings sit out on the porch or around the fire pit and enjoy the peaceful surroundings. You are only a 1-2 minute walk or drive from the public boat ramp. It is only located approximately one hour from Mammoth Cave National Park. There is a dedicated workspace for your remote work and high speed internet.

Superhost
A spacious living area features two recliners and a black dining table with six chairs. Large windows allow natural light to fill the space. The modern kitchen is equipped with stainless appliances, visible through an open design, while a ceiling fan provides air circulation.
Home in Leitchfield
4.88 out of 5 average rating, 16 reviews

Hip 2 Bedroom Home - Leitchfield

Refreshed in September 2024! Located in a rural, quiet town off the WK Parkway in Leitchfield. We are in a great central location to Elizabethtown, Mammoth Cave and Rough River & Nolin Lakes. This 850 sq. ft. home features 2 bedrooms and 1 small full bath, and large HDTVs. You’ll find stainless appliances, a Keurig, pots, pans and other necessities in the kitchen. In the bedrooms you'll find a comfortable memory foam bed as well as a TV, nightstand, dresser and desk.

Guest favourite
The living area features a cozy seating arrangement and a small television unit. A door leads to an outdoor area, allowing natural light to brighten the space. A wooden dining table and chairs are visible, along with warm wooden flooring that enhances the inviting atmosphere.
Holiday home in Leitchfield
4.85 out of 5 average rating, 109 reviews

My Blessing 5, at Rough River Lake area!

Rough River Lake Area, Cozy, peaceful apartment, in a Christian community, in McDaniel's, KY. Near Rough River State Park. Campgrounds nearby, 60 minutes to Mammoth Cave National Park. Lake beaches nearby. 45 minutes from Glendale. There is not room for boats or trailers, only for two vehicles per apartment. A good place to get away from the noise of the big cities, great to rest and enjoy nature. Our address is 14409 South Hwy 259, Apt. 5, Leitchfield, KY 42754

Top guest favourite
Cabin in Cub Run
5 out of 5 average rating, 73 reviews

Wooded "Saltbox Cabin", Lake: 6 min walk, Kayaks!

Mammoth Cave: 50 minute drive Boat Ramp/Swim: 6 minute WALK, or drive down Firepit: 20 PACES Grocery/Marina: 8 minute drive Hiking, biking, mountain biking, spelunking, offroading, horseback riding, boating , river kayaking, fishing, golf, restaurants: 30 minutes or less! Located in the coveted Green Acres Neighborhood on a peninsula of Nolin! Your Saltbox Cabin is nestled on a hillside acre overlooking the wooded gravel road that leads down to the lake.

Superhost
Home in Hudson
5 out of 5 average rating, 3 reviews

Rough River Lakeside Cottage- Epic Views!

Fully renovated lakefront home on Rough River Lake with private dock and water access. Enjoy panoramic views, a serene pond with fountain, and a charming gazebo for outdoor dinners. Multiple porch swings and spacious decks invite you to unwind, while modern comforts make this retreat perfect for family or couples. A true place of respite, relaxation, and connection by the lake.The whole group will be comfortable in this spacious and unique space.

Popular amenities for Grayson County holiday rentals