Vacation rentals in Grayson County

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Top-rated vacation rentals in Grayson County

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Guest favorite

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, 141 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!

Guest favorite

The interior of the tiny house features wood paneling and a cozy layout. An adjustable electric bed is positioned next to a pull-out sofa, with a dining table nearby. A loft area is accessible by a ladder, while a kitchenette with modern appliances is prominently displayed.

Tiny home in Leitchfield

5 out of 5 average rating, 5 reviews

Private Lake Access - Tiny House

Escape to our newly renovated tiny house on Rough River Lake! Private lake access and stunning views on 2 acres. Secluded retreat with modern amenities, surrounded by woods. Perfect balance of comfort and nature - relax on the front porch, at the fire pit, or stroll to the water. Your cozy lakeside hideaway awaits. WiFi and half kitchen with everything you need. This tiny house has everything you need for a memorable weekend. Only minutes from marinas, restaurants, and an hour from Mammoth Cave!

Top guest favorite

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, 137 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.

Superhost

Home in Cub Run

4.8 out of 5 average rating, 115 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 favorite

A dining area features a wooden table surrounded by six chairs, set against a backdrop of exposed brick walls and large windows. The adjacent living space contains a cozy seating arrangement with a sofa and armchairs, illuminated by warm light fixtures.

Apartment in Leitchfield

5 out of 5 average rating, 23 reviews

The Eleanor / Historic Downtown Hotel / 2BR/2Bath

Welcome to The Eleanor! This newly renovated 2-King bedroom / 2-bathroom apartment gives elegant big city vibes. You will enjoy natural light in every room with a panoramic view of the downtown square. With a fully equipped kitchen, you can cook a 5-star meal or walk outside and enjoy the easy access to the city's shopping, dining, & entertainment venues. Your whole group will be comfortable in this elegant and unique apartment inside the Historic 1935 Alexander Hotel. #leitchfield #kentucky

Guest favorite

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.

Apartment 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 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

4.86 out of 5 average rating, 14 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, large HDTVs with YouTube TV. 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 favorite

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.

Vacation home in Leitchfield

4.86 out of 5 average rating, 106 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

Superhost

A small white house with a red roof is surrounded by a spacious yard, featuring a wrap-around deck that provides accessible entry. Lush green trees and blue skies complement the relaxing atmosphere, while a gravel path leads towards the entrance.

Cottage in Falls of Rough

4.81 out of 5 average rating, 180 reviews

Kentucky Comfort

Small house with a beautiful wrap around deck overseeing a big pond. Small, simple, and set up for a relaxing get away with the family! The entire house is accessible for a wheelchair including the wrap around deck. Fishing and boating is also with in 10 minutes away at the Rough River Dam State Park. Wifi is fast if you have work to get done, also a small work desk is in the main bedroom. A TV and two big recliners is set up in the living room for lounging.

Superhost

A quaint cabin is nestled among tall trees, featuring a shaded porch with seating. The yard is covered in gravel, providing space for outdoor activities. A fenced area is indicated, suggesting a separation for pets and enhancing the private, serene environment of the property.

Cabin in Falls of Rough

4.76 out of 5 average rating, 209 reviews

Rough River Lake Cabin close to ramp pet friendly!

Quaint little cabin in the Indian Valley neighborhood of Rough River Lake with WiFi. The community boat ramp is convenient for fisherman and recreational boaters with plenty of parking both at the ramp and cabin for the boats! Nearby attractions are Rough River, Nolan Lake (40 miles), Mammoth Cave (45 miles), Lafayette Golf Club, and many more. 15 minutes from Leitchfield 50 minutes from Owensboro 1:20 minutes from Louisville 30 minutes from Hardinsburg

Top guest favorite

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.

Guesthouse in Leitchfield

5 out of 5 average rating, 133 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

4.87 out of 5 average rating, 162 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!