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, 143 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!

Superhost

Tiny home in Cub Run

4.8 out of 5 average rating, 169 reviews

The Camden - Romantic Tiny Cabin Retreat - Hot Tub

Couples Retreat @ Nolin Lake. Tiny Home Cabin. Perfect Romantic Getaway. Only 14 mi to Mammoth Cave. Private Hot Tub Nestled Behind Cabin on Wrap Around Deck, Surrounded by Nature. Relax By the Fire Pit Under the Stars or In One of the Rocking Chairs On the Covered Front Porch. Snuggle Up On the Comfy Queen Foam Mattress In the Loft. Window Allows for Sunlight & View of the Stars at Night. Private Boat Ramp Just 500 yards From Cabin. ~Washer & Dryer ~Fast Wi-Fi ~Outdoor Eating ~Grill

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, 139 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 screened-in porch area features a hot tub adjacent to the water, with two cozy towels hanging on hooks. The wooden deck displays a serene view of the adjacent lake, framed by lush greenery.

Home in Mammoth Cave

4.97 out of 5 average rating, 29 reviews

NEW! Nolin Lakefront, Hot Tub, Kayaks, Fishing

Welcome to your perfect lakeside escape! This small, cozy cottage sits on a serene pointe overlooking Nolin Lake and offers an ideal mix of comfort and natural beauty. Our property offers shoreline access to the lake for swimming and kayak launching. We are prohibited from allowing guests usage of the dock but you may use the dock path for kayak launching. Enjoy stunning panoramic lake views, screened porch, hot tub, fire pit, corn hole, board games and more. 15 miles to Mammoth Cave Nat Par

Guest favourite

Cottage in Hudson

4.95 out of 5 average rating, 120 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!!

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

4.96 out of 5 average rating, 28 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 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

4.87 out of 5 average rating, 15 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

4.86 out of 5 average rating, 107 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, 181 reviews

Kentucky Komfort

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

4.75 out of 5 average rating, 215 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 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, 144 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.