Holiday rentals in Grayson County

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Top-rated holiday rentals in Grayson County

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Top 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, 149 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, 144 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.

Top guest favourite
Two outdoor lounge chairs are positioned on a spacious green lawn, overlooking a vast landscape of trees and fields. A clear blue sky with scattered white clouds creates a serene atmosphere, inviting relaxation and enjoyment of the countryside view.
Flat in Morgantown
5 out of 5 average rating, 66 reviews

Scenic/Quiet Country Barndo Apt

Now offering HIGH SPEED INTERNET! Come escape to this peaceful 60 acre scenic countryside getaway w/walking trails, wildlife & catch & release pond. The apartment has a full modern kitchen with bath, heat, A/C, and patio overlooking a beautiful landscape. It sleeps 2 and can add 2 with available XXL cots with bedding. We are within 30 minutes from Beaver Dam Amphitheater & Rough River, 45 minutes to Bowling Green, & an hour to Mammoth Cave Nat'l Park & Nolin Lake State Park. WMA hunting nearby.

Top guest favourite
A covered deck area features a circular table surrounded by four metal chairs, set against a backdrop of lush green trees. The wooden structure provides a shaded space, ideal for outdoor dining or relaxation.
Home in Leitchfield
4.98 out of 5 average rating, 133 reviews

Special Mammoth Cave & Nolin Lake

Relax and enjoy this peaceful home at Nolin Lake. Located in the lake community of Annetta/Ambassador Shores. Lake access is about a 10-minute walk or 6/10 mile to the ramp. Rent a dock or boat (seasonally) at Moutedier Marina. Nolin State Park is close. Fishing & hiking in the area. Early mornings & dusk are best times to see our resident deer. Fire-pit in front yard, firewood available. Mammoth Cave & Dinosaur World about 30 miles away. 30 miles to Glendale. About 20 minutes to Leitchfield.

Superhost
A cabin exterior is illuminated at dusk, showcasing its wooden log structure with a steeply pitched roof. A spacious front porch features decorative lighting and a central green door, inviting visitors to enjoy the outdoors. The surroundings are tranquil, complemented by a clear evening sky.
Cabin in Falls of Rough
4.88 out of 5 average rating, 57 reviews

Doc's Place at Rough River, Lake Front Cabin

Escape to this cozy 2-bedroom, 1-bath cabin at Rough River Lake! Sleeping 6 with 3 beds, it overlooks the river banks and offers a fire pit area, picnic table, plus a front porch with rocking chairs. The kitchen is fully stocked with all-new pots, pans, dishes, and a coffee maker. Enjoy the provided indoor/outdoor games, bikes, books, fishing, kayaking, and a nearby golf course. Smart TV'S and high-speed WiFi for streaming available. Need something else? —just ask! As always pets welcomed!

Top guest favourite
Steps lead through a wooded area towards a serene lake visible through the trees. Sunlight filters through the leaves, casting a dappled light on the path. A kayak is partially visible along the water's edge, inviting guests to explore the outdoors.
Home in Leitchfield
4.96 out of 5 average rating, 28 reviews

The Lake House at Rough River

Bring the whole family to this Lake front property with lots of room for fun! Enjoy the lake and swimming just steps from the screened in deck! Divided on three levels are 4 spacious bedrooms, 2.5 baths, open concept kitchen and living, 2 living areas, and 3 decks to enjoy! There are two sets of stairs inside the home and steps outside the home. Please keep this in mind when booking! Rough River Lake is a U.S. Army Corps of Engineers waterway. The water level fluctuates with the season.

Guest favourite
Cabin in Leitchfield
4.9 out of 5 average rating, 182 reviews

Rough River Lake Vacation Rentals hot tub WIFI

Our beautiful custom waterfront cabin is a perfect getaway for couples and small families. We are located on Mercer Creek Cove. The cabin is very relaxing and private. There is a boat ramp in the subdivision for your use. All bedding and bath towels are included. Kitchen is fully equipped, direct tv on 3 large flat screen TVs. Gas grill we provide the propane, custom built in bonfire pit just steps from the water. Hot tub that overlooks the Cove, private outdoor shower. We now have WIFI!

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
4.86 out of 5 average rating, 115 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

Guest favourite
A spacious living room features a large sectional couch adorned with various patterned pillows. A wooden coffee table sits in front, displaying a small bowl of snacks. Light flows in through a window, which is dressed with sheer curtains, and wooden walls add a rustic touch.
Home in Caneyville
5 out of 5 average rating, 13 reviews

The Way We Were

Transport yourself back in time as you relax with the whole family in this peaceful and comfortable cottage. Located on a main road, but definitely in the country, " The Way We Were" has been completely gutted and remodeled while keeping some eclectic remnants of the past. Whether you are passing through, here on business, taking in a local concert or visiting,"The Way We Were" will fill the bill. Sit down and stay a while at "The Way We Were".

Superhost
Home in Hudson
5 out of 5 average rating, 4 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.

Top guest favourite
A television is positioned on a dark wooden stand beneath a decorative sign that reads 'FAMILY.' A potted plant adds a touch of greenery on the stand. Light-colored walls and a door with a window create a welcoming atmosphere.
Guest house in Leitchfield
5 out of 5 average rating, 160 reviews

The Treehouse

Keep it simple at this peaceful and centrally-located 2 bedroom, 1 bath second floor apartment. Fully furnished, cozy, and located right in the center of Leitchfield. Also centrally located between Rough River (10 minutes) and Nolin lake (22 minutes) with room for boat trailer parking. With restaurants and grocery stores less than 5 minutes away, this apartment is also perfect for extended stays. Both bedrooms are furnished with queen beds.

Superhost
A peaceful covered porch is visible, featuring two red rocking chairs. Lush green grass extends from the porch to the riverbank, where a calm river flows, and a fire pit is located nearby. Trees provide shade and enhance the serene outdoor setting.
Cabin in Falls of Rough
4.83 out of 5 average rating, 188 reviews

Waterfront Cabin with Hot Tub

Relax with the whole family in this adorable riverfront cabin. Gather around a campfire, cookout, fish, kayak, or go for a dip in the hot tub all from the backyard. And if that's not enough, take a stroll around the resort and immerse yourself in the beautiful scenery, historic falls and Green Farm, golf course clubhouse, and more! Oh and don't forget Rough River Lake and the State Park are just minutes away!

Popular amenities for Grayson County holiday rentals