Vacation rentals in Tompkinsville

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Top-rated vacation rentals in Tompkinsville

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Guest favorite
A two-story farmhouse is set against a twilight sky, featuring a modern gray exterior with a metal roof. The front door is framed by large windows, and expansive greenery adds to the peaceful scenery, highlighting the spacious environment around the property.
Home in Tompkinsville
4.95 out of 5 average rating, 95 reviews

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.

Top guest favorite
A hot tub is situated on a deck, surrounded by trees. The bubbling water can be seen, while a pair of bare feet rests on the edge. Soft light filters through the foliage, creating a serene atmosphere.
Cabin in Hilham
4.98 out of 5 average rating, 288 reviews

#3 Talley's Cabins by Dale Hollow Lake

Welcome to Talley’s Cabins near beautiful Dale Hollow Lake nestled in the Upper Cumberland area of TN. A quiet, peaceful and clean stay in the beautiful hilltops. With 47 acres to enjoy including hiking trails, scenic grounds to snap a picture, your own hot tub and fire pit. We are also just a short drive to some great attractions such as: Cummins Falls State Park, Standing Stone State Park, and numerous marinas surrounding the beautiful No. 1 Houseboat Lake on the Continent, Dale Hollow.

Top guest favorite
A cozy living area is highlighted by wooden walls and natural light. A dining table with chairs occupies one side, while a comfortable leather sofa with accent pillows faces a decorative fireplace. A chandelier hangs above, emphasizing the inviting ambiance.
Cabin in Moss
4.98 out of 5 average rating, 444 reviews

Tennessee Retreat Log Cabin Near Dale Hollow Lake

Tennessee Retreat Log Cabin, nestled in the hills of the Eastern Highland Rim, has everything you need to escape in style. Amenities (like WiFi and Cable TV) let you enjoy the serenity of the woods with casual or formal dining, antique or necessity shopping, water activities on Dale Hollow Lake - a 15 minute drive, wineries, historic & natural attractions & live entertainment. Perfect for business or pleasure trips, extended stay or hosting weddings or events on the extensive lawn. Welcome!

Guest favorite
A spacious modern home features dark metal siding and multiple large windows. A covered porch is present at the front, with several chairs arranged for outdoor seating. The surrounding landscape includes grassy areas and trees, contributing to a rural charm.
Farm stay in Monroe County
4.86 out of 5 average rating, 44 reviews

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

Top guest favorite
A contemporary dairy barn showcases a welcoming façade featuring green siding and a spacious covered porch. A sign for Kenny's Farmhouse Cheese is prominently displayed at the entrance, with farm equipment parked nearby, set against a backdrop of rolling green fields.
Farm stay in Austin
4.96 out of 5 average rating, 375 reviews

One of a Kind Farmstead Experience

A one of a kind farmstead experience, stay in a newly constructed barn on our 350 acre dairy farm. The Mattingly farm is home to Kenny's Cheese, farmstead cheese made right here on our farm and you have a unique opportunity to stay in the heart of the action, in our brand new apartments directly above the dairy barn. You will be welcomed by our friendly dairy cows and possibly a new baby calf, or two. And because our cheese is AMAZING, we will leave some in the fridge for you to try.

Top guest favorite
A shallow creek flows gently through a wooded area, lined with trees. Smooth stones and pebbles are visible along the water's edge. A person stands mid-stream, with water reflecting the surrounding greenery. Soft light filters through the leaves, creating a peaceful ambiance.
Home in Summer Shade
4.98 out of 5 average rating, 107 reviews

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.

Superhost
The open living area features two comfortable couches, one in light fabric and one in dark green. A TV is positioned on a console, with a dining table set nearby. Natural light enters through a window, complemented by neutral décor and wood-style flooring.
Home in Red Boiling Springs
4.69 out of 5 average rating, 16 reviews

Salt Lick Creek Cottage

Welcome to Salt Lick Creek Cottage, a cozy retreat in a charming historic district. This quaint country cottage is ideal for couples, solo travelers, or small families seeking a peaceful getaway and is close enough to Nashville and other hot Tennessee destinations. Across the street is a beautiful town park with a playground, meandering walking paths, and a scenic creek that flows through town. This relaxing countryside escape offers comfort, charm, and a touch of nostalgia.

Top guest favorite
A charming farmhouse is presented with a classic design and a metal roof. The front porch features seating arrangements, surrounded by neatly landscaped greenery. Large windows allow natural light to enter, while a swing chair invites relaxation. A peaceful setting is emphasized by the surrounding landscape.
Home in Monroe County
4.97 out of 5 average rating, 36 reviews

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.*

Top guest favorite
The historic two-story brick house is framed by a well-maintained lawn featuring a variety of shrubs and flowers. A covered porch extends across the front, marked by white rocking chairs and supported by large columns, inviting relaxation in the shade.
Home in Tompkinsville
4.91 out of 5 average rating, 103 reviews

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.

Top guest favorite
The exterior of a Victorian-style house is showcased, featuring intricate architectural details and a blue facade. The home is surrounded by a manicured lawn and small shrubs, with a welcoming porch and decorative gables highlighted above the entrances.
Home in Gamaliel
4.98 out of 5 average rating, 123 reviews

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.

Top guest favorite
A wooden cabin is set amidst lush greenery, featuring large windows that allow natural light to fill the interior. A spacious deck, surrounded by trees, invites outdoor relaxation. Stairs lead down to the cabin entrance, blending harmoniously with the surrounding forest.
Cabin in Jackson County
4.98 out of 5 average rating, 328 reviews

Brae Cabin - Nature Surrounded and Tech Connected

Relaxation, Romance, and Nature. Brae Cabin is a beacon that matches your wants and needs. The outdoor night is transformed by the Enchanted Forest light show. Secluded in nature with just the right amount of technology to be interesting. The trails start at the entrance of Brae Cabin. Walk to Mt. Cameron or the Outpost (the cabin with an outhouse). An experience awaits. Hugh and Nancy welcome you!

Guest favorite
A cozy tiny cabin is set amid a gravel area, surrounded by trees. A hammock is gently draped between posts, while wooden chairs are placed nearby. The cabin features a porch with a railing and string lights, extending a welcoming atmosphere.
Tiny home in Celina
4.97 out of 5 average rating, 129 reviews

Sunset Ridge Cabin- Snow Hill Farm

Our cozy tiny cabin is the perfect get away for your vacation. Come relax just 10 minutes from beautiful Dale Hollow Lake in our peaceful location here in Celina, TN. Our goal is to allow you to unwind and put a pause on the craziness of everyday life. Enjoy your cup of coffee with a view of our rolling hills pasture and farm animals. *All natural cleaning supplies used. Yay for a chemical free vacation!*

Popular amenities for Tompkinsville vacation rentals

  1. Airbnb
  2. United States
  3. Kentucky
  4. Monroe County
  5. Tompkinsville