Holiday rentals in Grayson County

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Top-rated holiday rentals in Grayson County

Guests agree: these stays are highly rated for location, cleanliness and more.

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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

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.

4.98 out of 5 average rating, 164 reviews

Top guest favourite

A dining area features a rustic table surrounded by black chairs, complemented by decorative wall art made of woven circles. A light fixture hangs above, while a marble countertop is visible in the foreground, showcasing a plate of cookies and a fruit display.

Flat in Leitchfield

The Alexander Hotel -The McKinzie Suite- 2BR/2Bath

Welcome to The McKinzie! This newly renovated 2-King bedroom / 2-bathroom penthouse gives big city vibes. You will enjoy natural light in every room with a spacious open concept for the living, kitchen and dining area. 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 fun and unique apartment inside the Historic 1935 Alexander Hotel. #leitchfield

5.0 out of 5 average rating, 33 reviews

Guest favourite

A cozy cabin with a metal roof is set against a backdrop of lush greenery. The front porch features seating, while a children’s playset, complete with slides and swings, is visible in the yard. The serene environment is ideal for family relaxation.

Cabin in Rough River

Brand New Cozy Cabin near the lake

Relax with the whole family at this peaceful place to stay. Enjoy a cup of coffee on the front porch swing while taking in beautiful scenery with the occasional visit from a fox or a deer. Tranquil Lake view is only a short walk away. The cabin is located minutes away from state resort, restaurants and dollar store. Enjoy using the pit boss grill or the gas grill. There is also a nice fire pit that can be enjoyed anytime of year. There is unlimited WiFi as well.(2 OF THE BEDROOMS ARE JOINED

4.91 out of 5 average rating, 77 reviews

Guest favourite

A spacious deck is highlighted by several green Adirondack chairs and a picnic table beneath a wooden pergola with string lights. A hot tub is visible nearby, with a natural setting of trees in the background and a colorful sky at dusk.

Cottage in Hudson

Hot Tub, Large game area, book fall dates today!

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!!

4.95 out of 5 average rating, 137 reviews

Top guest favourite

The front exterior showcases a charming Craftsman home with gray siding and white trim. A covered porch features white railings and steps leading to a landscaped yard with shrubbery. Bright blue skies create a welcoming atmosphere, highlighting the home's inviting entrance.

Home in Leitchfield

-Magnolia On Main- Central locale near the Square

Completely remodeled in 2023, this charming Craftsman in the heart of Leitchfield is walkable to Boutiques, the Storehouse Coffee, the Spa on Main & the Historic Jack Thomas House. You are sure to feel at home in this spacious 3 BR home with easy access to parks, groceries & our revitalized town square. Magnolia on Main is nestled between Rough River & Nolin Lake & only minutes from the Leitchfield Aquatic Center, Industrial Park & Owensboro Twin Lakes Hospital. 3 minutes from Western Ky Pkwy.

5.0 out of 5 average rating, 21 reviews

Top guest favourite

Home in Grayson County

Private Lake Home w/FirePit, Arcade, & Game Table

Forget your worries in this spacious and serene lakehouse with tons of outdoor space! This home nestled on 4.5 acres only 2.2 miles from the Iberia Boat Ramp features a large U-shaped driveway perfect for parking of multiple boats. Enjoy the screened in porch with outdoor fireplace, upper level deck, and 2 porches with outdoor fans to cool you down in the Summer months! The large vaulted open concept family room and basement are perfect for entertaining large groups. Relax, unwind, and enjoy!

5.0 out of 5 average rating, 30 reviews

Top guest favourite

Home in Westview

Rough River Lake | 5BR Waterfront | Sleeps 15

Bring your crew to Rough River Lake. This 5BR lake house sits on the water on George's Branch, overlooking the water ski slalom course. Sunsets from the deck, then down to the lake in the morning. Sleeps 15. Cook in the open kitchen, gather by the stone fireplace, or dine at the 12-person table on the porch overlooking the lake. Finished basement has a wet bar, ice machine, game tables, and a daybed swing overlooking the water. Firepit, double-decker porches, water toys, quiet neighborhood.

5.0 out of 5 average rating, 18 reviews

Top guest favourite

A spacious outdoor living area features comfortable wicker seating arranged around a central coffee table, with a large dining table in the background. A gas grill is present, and the space is surrounded by greenery, providing a serene atmosphere for relaxation.

Home in Falls of Rough

Porch-lovers paradise! Sleeps 11-12

Relax with family and friends at this peaceful place to stay. Welcome to our 3BR 2BA fully equipped lake house with an amazing outdoor entertainment space. Enjoy the sunrise on the covered front porch, and sunset on the covered back patio with a view of the lake. Equipped to sleep 11 people comfortably, ample parking space for cars and all of your toys. Two driveway entry points, electric car charger outlet. Less than a mile from the public boat ramp! We allow pets but must be authorized.

5.0 out of 5 average rating, 25 reviews

Top guest favourite

Home in Clarkson

Luxury Family Retreat Nolin Lake & Wax Marina

Lake days, sunset fires, and unforgettable memories await! This spacious retreat is minutes from Nolin Lake, Mammoth Cave, Iberia Beach, and Wax Marina. Enjoy the open-concept layout, chef's kitchen, walkout basement for games and movie nights, covered porch with scenic views, and fire pit under the stars. Perfect for families, groups, and reunions, with easy access to Mammoth Cave, hiking, golf, and lake adventures. Book your Nolin Lake getaway today! Ask about Pet Fees & Golf Cart Rentals!

5.0 out of 5 average rating, 18 reviews

Superhost

Home in Leitchfield

Eagle Nest Nolin Lake Mammoth CaveLuxury Retreat

Eagles Nest - Private family getaway! Completely renovated 4 bedroom 3 full bath 5 min to Nolin Lake (Moutadiere Marina) & 40 min to Mammoth Cave. Unique, stylish decor, luxurious linens, HOT TUB, firepit, full Margaritaville styled bar w pool table, pac man machine & dance area. Large covered deck w/ dining area, conversation area. Kitchen has everything you need to prep full meals, bedrooms w/ amazing mattresses, 5 flat screen TV's. Back patio has blackstone & gas grill.

4.86 out of 5 average rating, 145 reviews

Top guest favourite

Home in Clarkson

New luxury home near Nolin Lake and Mammoth Cave!

A newly built 3,500 sq ft getaway designed with both luxury & fun! This modern new-build home blends sleek finishes w/ cozy touches, creating the perfect escape for families & groups. Step into a game lover’s paradise ft. multiple gamerooms, a hockey table, a smart TV or kick back in our inviting lounges! Each bedroom is giving adults hotel-style comfort while kids will love the endless fun. Enjoy the peace of a private yard! Make your stay unforgettable, book now!

4.96 out of 5 average rating, 24 reviews

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

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.

4.99 out of 5 average rating, 187 reviews