Holiday rentals in Monroe County

The Crossing

The newly renovated two bedroom farmhouse is located less than 2 miles from the city limits of Tompkinsville, KY and 3 miles from the Tompkinsville airport. Local attractions include the Old Mulkey Meeting House, restaurants, and a short drive to Dale Hollow Lake. The Crossing was built in the late 1890’s in the shape of a cross. The original house has stunning 9 foot ceilings and beautiful fireplaces in the four original rooms. Includes new appliances, Wi-Fi and outdoor space for dining.

Unique & Authentic Farm Experience

A truly one of a kind farmstead experience -stay in a newly constructed barn apartment on our 500 acre dairy farm. The Mattingly farm is home to Kenny's Cheese - farmstead cheese made right here onsite. This is a unique opportunity to stay in the heart of the action, in our modern apartments directly above the dairy barn. You will be welcomed by our friendly dairy cows and possibly a new baby calf or two. Simply because our cheese is AMAZING, we will leave some in the fridge for you to try!

New cozy home, real working farm

Beautiful brand new home on 93 acres allows breathtaking views of sunrises and sunsets across the pond and around the fire while allowing you to get away to country life. 40 minutes from Dale Hollow Lake, 35 minutes from Barren River Lake, 75 minutes from Lake Cumberland and 90 minutes from Nashville, this is the perfect location for your country getaway. Note: this is a real operating farm so please be cautious. Also, we welcome hunters but staying in our home does not grant access to hunt

Pine Grove BNB

Located minutes from the heart of Tompkinsville, experience the charm of our renovated, early 1900's cabin that is professionally landscaped with ambient outdoor lighting. You'll feel miles away nestled among a historic pine grove overlooking more than 100 acres. A respite for those looking for adventure and R&R alike, we welcome anyone in search of a creative getaway, restorative time for themselves, & those wanting to escape to a curated & welcoming space to find a little peace & clarity.

Quiet country farmhouse near creek

Make some memories at this unique and family-friendly place. Located on our family farm and on Skaggs Creek. Enjoy country living and the beauty the creek has to offer. During the late summer you can enjoy the bounty of our family garden. From any direction you are about 45 mins from Bowling Green, Barren River lake, Dale Hollow Lake, and Mammoth Cave; and about 1.5hrs from Nashville. Or choose to stay close and enjoy the local arts and theater! This home is located on a family farm.

Cozy Studio Cabin Tiny House

This lovely 1-bathroom studio may be small in size, but it’s big on charm! Nestled near the peaceful town of Fountain Run, this vacation rental boasts easy access to outdoor adventures and small-town fun. Bring your boat and fishing gear along for fun on the water of Barren River Lake or explore the trails in the Brigadoon State Nature Preserve. Enjoy the low-key setting with a home-cooked meal on the wraparound porch or head out to a local classic Kentucky barbecue.

The Howard House at Miller Farms

This adorable farmhouse is for those seeking a quiet spot to unplug and rejuvenate on a beautiful farm in Southern Kentucky. There is a gorgeous farm view from the porch swing. This is the perfect place to enjoy the sound of crickets and the night starlight. An ideal retreat for families, individuals, couples, or friends. We can’t wait to share our corner of the world with you. *This is a working farm so please be cautious with animals and moving equipment.*

Charming Cabin in the Hollow

Come stay in our peaceful setting located between a creek and a spring, down in the holler! Once inside, enjoy the space we have worked hard to create. The main floor is open concept through from the living room to dining and kitchen. The master bedroom is complete with its own bathroom and tile shower! A unique floating staircase reaches up to the loft area where a large sitting room and dorm style sleeping area combine. Lots of room to play games!

Unique 1805 Historical House

The Old Brick House is located within minutes of Tompkinsville. It is situated on 3 acres of land where you can hear the sound of tree frogs at night and the creek running across the road. This property is well shaded with lots of outdoor space perfect for a quiet get a way for couples or families. This home can sleep six individuals comfortably. So if you are looking to relax & enjoy some history, please come stay at The Old Brick House.

Rich's Farm House

This home away from home is a spacious 4-bedroom and 2-bath house with washer & dryer, WiFi, outside grill, handicap accessible back door and touchpad entry/lock and many more amenities to ensure a comfortable stay. This beautiful property is conveniently located near Tompkinsville, KY and Dale Hollow Lake at Celina, TN. Please don't hesitate sending a message to us with any questions. We look forward to having you come stay with us soon!

The Jackson House of Gamaliel

Stay at The Jackson House of Gamaliel. The Victorian style house was originally built in 1904 and underwent a total remodel in 2017. You will be the only guests in the house. One King bed, two Queen beds and a sofa sleeper. Kitchen with all cooking utensils, a laundry room and a large living area. Convenient to Dale Hollow Lake and Barren River Lake, (Approx 30-45 minutes). Near Old Mulkey Meeting House State Park.

Limestone Lakehouse at the Cove

Relax with the whole family at this peaceful place to stay. This Lakehouse has a beautiful view of the lake from the back porch with a primitive firepit in the woods. The house will sleep 14 (2 full size beds in the finished basement, two king and one full bedroom). The loft is perfect for children with 4 twin beds. The lake offers great fishing and kayaking and there is an abundance of wildlife.