Holiday houses in Simpson County

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Top-rated holiday rentals in Simpson County

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Top Guest favourite
A charming guesthouse is shown with a mix of light and dark exterior siding. The front door is adorned with a circular wreath, while multiple windows allow for natural light. A pathway of stones leads to the entrance, surrounded by green grass.
Cottage in Auburn
5 out of 5 average rating, 52 reviews

Meadow Lane Cabin

Enjoy our tiny guesthouse on our little farm. We are right off the Hwy 68/80, home of the 400 mile yard sales. Straight shot to Bowling Green, approx 2O miles. Dollar General close by for your basic needs. We are happy to provide a free breakfast and hot coffee for your stay. Also, we are super excited that two new coffee trailers have opened within five miles of the listing. Knox Coffee Co and Grounded Coffee Co offer coffee beverages and pastries, located off the 68/80, towards Bowling Green.

Top Guest favourite
The farmhouse exterior is framed by mature trees, offering shade and a welcoming presence. A wooden porch with steps leads to the entrance, surrounded by fresh landscaping and a lightly manicured lawn. The tranquil countryside setting is visible in the background.
Home in Alvaton
4.95 out of 5 average rating, 39 reviews

Little House on Old Dearing

This quaint farmhouse is located in Alvaton, KY sits on one acre surrounded by 50+ acres of quiet countryside. It is just a short 10 minute drive from I-65 and for those passing through just an hour north of Nashville. We are about 20 minutes from WKU, 30 minutes from Barren River Lake, and about 45 minutes from Mammoth Cave National Park. There are also many creeks around which is a very popular summer activity in the area. We have Kayaks for rent for those interested! Pet friendly AirBNB

Top Guest favourite
A vibrant red Corvette is parked in front of a charming ranch-style home, featuring a covered porch with multiple rocking chairs. The property is surrounded by a well-maintained lawn and landscaped pathways, with trees in the background under a clear blue sky.
Home in Bowling Green
5 out of 5 average rating, 79 reviews

Enjoy Family Fun Without Leaving the Property

At Horsepower Hangout of Kentucky, you will experience a fun space full of activities for the entire family in a relaxing, peaceful, spacious, & safe location. The home sits on 1.3 acres with 30 trees! You’ll be close to local attractions: The Corvette Museum, Mammoth Cave, & Beech Bend Raceway. The two-car garage is the perfect place to park your vehicles. You will enjoy a full kitchen, recreation room, 70” smart TV, gaming system, ping pong, corn hole, foosball, fire pit, sunroom, & king bed!

Guest favourite
The cabin features a two-story log structure with a welcoming entrance, framed by manicured greenery. A brick pathway leads to the front door, while large windows allow natural light to enhance the rustic charm of the exterior.
Cabin in Franklin
4.86 out of 5 average rating, 152 reviews

HUGE I-65 Hideaway Cabin/ Franklin/Ext stay disc.

Located just off I-65, this spacious and historically rich cabin offers a one-of-a-kind stay that feels like stepping into a museum—with all the modern comforts you need. Relax on the huge back porch, grill out, or gather around the fire pit for cozy evenings. Inside, enjoy a lofted living space, fast Wi-Fi, and a washer/dryer for extended stays. Whether you're here for a weekend getaway, work trip or a longer escape, this cabin is perfect for families, remote workers, and history lovers alike.

Top Guest favourite
A cozy outdoor seating area features bright blue chairs arranged around a table with a fire pit. Flames dance atop a bed of decorative stones, while a charcoal grill is visible in the background. A sunset casts warm hues across the open field.
Home in Portland
4.98 out of 5 average rating, 80 reviews

Romantic cozy cottage

- Quaint country cottage on a private lane - Perfect for couples or small family - King-sized bed in master bedroom; full-sized bed in second bedroom - Located between Nashville, TN & Bowling Green, KY off I-65; close enough to be in these locations & activities within an hour - Peaceful sunsets & scenic farm views - Fire pit and charcoal grill provided for outside enjoyment - Remodeled bathroom and all new flooring throughout (Cottage formerly known as "Bill's Cottage" to returning guests.)

Top Guest favourite
A serene sunset is captured behind two leafless trees, casting a silhouette against a soft orange sky. Mist envelops the field, adding a layer of tranquility. The landscape extends softly into the distance, enhancing the peaceful rural atmosphere.
Home in Portland
4.92 out of 5 average rating, 225 reviews

Peaceful, chic farmhouse north of Nashville

We have free high-speed Wi-Fi - ideal for remote workers and TV bingeing. Perdue Farm is great for family gatherings, rejuvenation, and professionals. The interior is spacious with lots of natural light. The whirlpool tub offers relaxation and restoration. Outside, enjoy the wide open spaces. Soak in the amazing sunsets around the firepit in the back garden. Your stay at The Perdue Farm offers relaxation, fun family times, and a tranquil experience. Book your Tennessee adventure now!

Guest favourite
A well-maintained two-story farmhouse is set against a backdrop of lush grass and tall trees. A spacious porch features white railings and several decorative elements. The home is surrounded by an open area, creating a peaceful countryside atmosphere.
Home in Auburn
4.93 out of 5 average rating, 15 reviews

Farmhouse at Black Lick Creek

The Family Farmhouse sits on a 263 acre farm nestled among Black Lick Creek. It is located at the back of the farm, so it is very quiet. The property is gated, and the owner is the only other resident on the farm living in an adjacent house. You will be minutes from town but nestled away in your own peaceful country setting. The entire first floor is included for use in the rental. The upstairs bedrooms have not been converted for guest, but the upstairs landing does have a full size bed.

Top Guest favourite
A two-building structure is depicted, featuring a main house with a wraparound porch and a side building with a garage. The landscape surrounding the buildings includes a grassy area and distant trees under a cloudy sky.
Guest suite in Alvaton
4.98 out of 5 average rating, 139 reviews

Large upstairs Country bungalow, peaceful,spacious

Country peaceful living. New home, 10 minutes to mall, restaurants and the Corvette Museum. 15 min to downtown Bowling Green & WKU. 70 miles to Nashville and 45 minutes to Mammoth cave. Fenced area to board horses. Upstairs 900 sq ft bungalow in main house with private entrance, extra-large BR with 2 Qn beds, large LR, bathroom with shower, microwave, coffee maker, toaster and small refrig. No stove or kitchen sink. Children's play area. Daily, wkly, monthly rental No smoking, no pets

Top Guest favourite
A spacious living area is highlighted by a sleek leather sofa and a wooden coffee table. Floor-to-ceiling windows allow natural light to fill the room, while a ceiling fan provides airflow. A wall-mounted TV is visible, along with a stylish art piece featuring a bull.
Home in Franklin
4.96 out of 5 average rating, 169 reviews

Pet-Friendly Modern KY Retreat | Cozy 2BR Home

Enjoy this renovated 1940s retreat in Franklin, KY! Perfect for work trips, romantic getaways, or weekend escapes! Full kitchen, two bedrooms with queen beds, washer and dryer, and fast, reliable Wi-Fi. Pet-friendly and welcoming to all, it’s perfect for families, couples, or groups! Just minutes from I‑65, you can easily explore Nashville, Mammoth Cave, and local Amish markets. Have questions or interested in long-stay pricing? Click “Contact Host” before booking—we’re happy to help!

Top Guest favourite
A spacious living area features a mix of leather and fabric seating arranged around a central coffee table. Exposed brick walls add character, while a ceiling fan provides airflow. A flat-screen television is positioned near a decorative fireplace, and a soft area rug enhances comfort.
Apartment in Franklin
4.9 out of 5 average rating, 90 reviews

Lovely Historic Spot ~ Walk to the Square!

This special place is close to everything, making it easy to plan your visit. Newly remodeled ground level apartment in a historic home- you will be close to shopping and restaurants in downtown Franklin, Kentucky. Walk to the square and enjoy your search for cool finds in local shops and enjoy the easy access to Nashville (45 minutes), Bowling Green (25 minutes), Mammoth Cave, the Corvette Museum, and so much more. About 5 minutes to I-65 makes getting in and out of Franklin easy.

Guest favourite
The front exterior of the bungalow showcases a classic white facade with black shutters framing the windows. A welcoming porch features a small welcome mat and a neatly landscaped area, including green shrubs and fresh mulch, enhancing the inviting entrance.
Home in Franklin
5 out of 5 average rating, 92 reviews

Hometown Hideaway

Come relax in this newly remodeled cozy bungalow. This two bedroom one bath home features everything you will need for a comfortable stay. Everything in this house is new and decorated with the guest in mind. A fully stocked kitchen including a coffee bar and complimentary snacks will make you feel right at home. The home has a private yard which is fully fenced in the back. There is also a fire pit and patio furniture. Making it the perfect spot to unwind after a long day.

Guest favourite
A charming farmhouse sits amidst a lush landscape, featuring a light-colored exterior and a metal roof. A driveway leads to a spacious attached garage. A basketball hoop is positioned on a smooth surface, providing a recreational area, while trees frame the property for added privacy.
Farm stay in Bowling Green
4.95 out of 5 average rating, 130 reviews

Hickory Springs-Peaceful/w/Adventure

Come and stay on this beautiful working farm on 24 acres with a fresh water Spring that flows over the rocks as you listen from the gorgeous deck. You will think you have entered a home built years ago but the Vintage farmhouse look inside this home says Reclaim, Refurbish, Reuse throughout ! Your family can play ball on your own Field of Dreams with lights for a great night game of baseball or whiffle ball. Come relax and enjoy Hickory Springs. Private and Peaceful.

Popular amenities for Simpson County holiday rentals