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, 145 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, 142 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
Cottage in Hudson
4.95 out of 5 average rating, 126 reviews

Hot Tub, Large game area, Ready for the holidays!

Cozy 3 bed 2 bath home nestled right along the banks of Rough River with little boat traffic. A community boat ramp is conveniently located behind house and the main lake is only a 15 min boat ride away. Only a short drive to the beaches of Rough River State Park. Plenty of sleeping area with King and Queen bedrooms and a Bunk room with 5 twin beds. The oversized garage will store a boat or kayaks while you visit. Enjoy a game of ping pong, pool or cozy up by the firepit!! Perfect for fishing!!

Superhost
Home in Cub Run
4.81 out of 5 average rating, 119 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

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

Doc's Place is sure to be your home away from home. With an ideal location overlooking the banks of Rough River this home is an outdoor lover's dream. Enjoy time rocking on the front porch, roasting marshmallows at the fire pit or playing any of our indoor and outdoor games. With comfort in mind we have made it a priority to make sure your every need will be met. The Kitchen has been stocked with all new pots, pans, dishes, coffee and everything in between. If we don't have it we will get it.

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, 31 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.

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, 129 reviews

Nolin Lake and Mammoth Cave

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 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, 110 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
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, 154 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.

Guest favourite
Cabin in Hudson
4.92 out of 5 average rating, 13 reviews

Rough River Lake Cabin- Stunning views, Hot tub!

Renovated lakefront cabin at Rough River Lake with stunning elevated views. Enjoy spacious decks, a hot tub overlooking the water, and the soothing sounds of a private pond with a fountain. Blending rustic charm and modern comfort, this peaceful retreat is perfect for couples or families seeking relaxation, privacy, and connection. From morning coffee by the fountain to evenings under the stars, every moment here is designed for serenity.

Popular amenities for Grayson County holiday rentals