Vacation rentals in Tompkinsville

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Top-rated vacation rentals in Tompkinsville

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

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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

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.

4.94 out of 5 average rating, 106 reviews

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

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!

4.98 out of 5 average rating, 456 reviews

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

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.

4.98 out of 5 average rating, 121 reviews

Top guest favorite

A small dining area is positioned in front of large windows, offering a view of the lake at sunset. A bottle and glass sit on the table, which is flanked by two benches. The warm hues of the setting sun fill the room.

Guest suite in Albany

Page's Legacy: Summertime Fun at the Lake

All rooms have a view of the lake and the deck overlooks Dale Hollow. We are a mile from Wolf River Boat Dock. The suite is downstairs with a private entrance. There are walking paths that encompasses 3 acres on the property. The private deck has a fire pit for chilly mornings to enjoy coffee or relaxing evening. There are some great day trips I have added to the "Host Guidebook" Click on "More about this location" and scroll to the bottom and click on "Show Host Guidebook"

4.98 out of 5 average rating, 293 reviews

Guest favorite

The two-story farmhouse showcases a classic exterior with white siding and green shutters. A covered front porch provides space for outdoor relaxation, while well-maintained landscaping featuring shrubs and stone borders enhances the welcoming vibe amidst a rural backdrop.

Farm stay in Austin

Farmhouse With a View @ Mattingly Farm

Get away from it all at our 350 acre working dairy farm. The Mattingly farm is home to Kenny's Farmhouse Cheese, farmstead cheese made right here on the farm using our own cow's milk. This area's country charm offers a relaxing lifestyle that will make the drive to this country landscape so worthwhile! Be sure to visit the dairy barn and view our new state of the art robot milkers. Enjoy the cheese samples left in your refrigerator to welcome you to the farm!

4.94 out of 5 average rating, 408 reviews

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

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.*

4.95 out of 5 average rating, 43 reviews

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

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.

4.92 out of 5 average rating, 111 reviews

Guest favorite

A cozy A-frame interior is shown, featuring a spacious bed adorned with pillows and a warm blanket. A small desk with two chairs is positioned by a window, while a wooden bench offers additional seating. Natural light enters through the window, highlighting the wood paneling.

Treehouse in Fountain Run

The EH Frame with Disc Golf in the woods!

Enjoy the lovely setting of this A Frame that is sitting on a bluff overlooking a creek through the trees. Behind the A Frame is an open meadow up top with a firepit area and also the shower house/washroom. From the parking area, you can walk up a trail to get up to the cabin; or if you have more of an off road vehicle you may drive up top and around to the back side of it. On quiet evenings, enjoy the woodland sounds and the creek below

4.96 out of 5 average rating, 102 reviews

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

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.

4.98 out of 5 average rating, 127 reviews

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

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!

4.98 out of 5 average rating, 334 reviews

Top 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

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!*

4.97 out of 5 average rating, 140 reviews

Guest favorite

A serene winter landscape showcases a blanket of snow covering the ground. Leafless trees stand next to a gently frozen lake, contributing to the tranquil ambiance. A home is partially visible in the background, surrounded by a peaceful forest setting.

Vacation home in Tompkinsville

Unique lakeside vacation home in Tompkinsville

This unique lakeside vacation home is located near Old Mulkey Meetinghouse State Historic Shrine and features 4 bedrooms, 2.5 baths. The open floor plan is decorated with Monroe County history and artwork and features 8 beds which can sleep up to 13 persons. Enjoy a walk along the lake's bank, kayak your afternoons away and enjoy the peaceful tranquility of small-town life.

4.89 out of 5 average rating, 45 reviews