Holiday rentals in Tompkinsville

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Top-rated holiday rentals in Tompkinsville

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Top guest favourite
The yurt is nestled among trees, featuring a large private deck that extends outward. Natural grassy areas surround the structure, and the exterior displays a neutral color contrasting with the greenery.
Yurt in Smiths Grove
4.99 out of 5 average rating, 148 reviews

Mammoth Cave Yurt Paradise!

Just 11 miles from the world's longest cave system, Mammoth Cave National Park, our yurt provides a unique glamping experience with many modern amenities. Inside, cook in the full kitchen or snuggle up and enjoy your favorite show on our smart TV. Outside, sit on our large private deck or around a stone fire pit where you can relax and enjoy the sounds of nature. Whether you're looking for a quiet retreat or an adventure-filled getaway, our yurt is the perfect choice for your next vacation.

Top guest favourite
A spacious log cabin, surrounded by green landscaping, features a covered front porch supported by wooden columns. Rocking chairs are positioned on the porch, inviting relaxation. A stone fire pit is visible in the foreground, with a blend of wooded areas providing a natural backdrop.
Cabin in Allons
4.94 out of 5 average rating, 252 reviews

Sweet Southern Retreat near Dale Hollow Lake

Welcome to the Cox-Dean Family Cabin near beautiful Dale Hollow Lake. Enjoy the peace and tranquility of 17 acres of undeveloped land from the comfort of an updated and well-equipped log cabin. Features 3 bedrooms, a loft with 4 twin beds, 2 bathrooms, a full kitchen, a board game closet, charcoal grill, a smart TV and fiber/gig speed internet. Central heat/air and city water/sewer. **NEW KITCHEN APPLIANCES AS OF JULY 2025** NOTE: We do NOT have cable or satellite TV, only streaming services.

Top guest favourite
A spacious outdoor deck features several red chairs facing a green metal barn exterior. The deck overlooks fields and trees in the distance, with two access doors leading into the apartment. The setting offers a glimpse of the rural landscape surrounding the farm.
Barn in Austin
4.98 out of 5 average rating, 406 reviews

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!

Top guest favourite
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, 426 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 favourite
A cozy sleeping area is located in a triangular loft with metal walls. A spacious bed is dressed in a vibrant green and blue patterned comforter. A decorative star-shaped light fixture adds character, providing soft illumination in the intimate space.
Flat in Lebanon
4.86 out of 5 average rating, 180 reviews

11 - Starfire 11 A-Frame Glamper B & B!

Closest to Restroom/Shower Building, Barn & Kitchen! THE STARFIRE 11 A-Frame Glamper has 2 queen size & 1 full size memory foam beds, WIFI, big screen smart TV, clean linens, window AC, wood burning stove, fridge, hammock, patio grill, picnic table, fire pit & other amenities. 32 mi to downtown Nashville! Complimentary Country Breakfast 7:00-11 a.m. at Jay Bob's Country Kitchen! Perfect for 4 to 6 peeps and a pet! Please list the correct number of guests when booking! Thanks!

Superhost
The cottage features a vibrant red metal roof and a welcoming porch with wooden chairs. A view of the surrounding area showcases greenery and buildings in the distance, including a clock tower, highlighting the cottage's proximity to the town center.
Cottage in Gainesboro
4.93 out of 5 average rating, 304 reviews

A vintage cottage in historic downtown Gainesboro

The Cottage is a private space conveniently located one block from the Gainesboro square in picturesque Jackson county. Close by are many outdoor activities such as fishing the Cumberland River or canoeing/kayaking on the Roaring River, where there is a boat ramp, a swim area & playground. Just 12 miles to Cummins Falls State Park & 25 minutes to Cookeville. If you’re a history buff, make sure to visit the incredible Jackson County Archives & Veterans Hall at 104 Short St.

Top guest favourite
A cascading waterfall is surrounded by lush greenery, with water flowing over rocky ledges into a serene river pool below. The scene is illuminated by a warm, golden glow of the setting sun, creating a tranquil atmosphere amidst the natural landscape.
Guest suite in Cookeville
4.99 out of 5 average rating, 215 reviews

The Suite at Waterloo Falls- entire suite

Located on Spring Creek, one of Tennessee's designated State Scenic Rivers, this property offers over 2,000 ft of river frontage, including 2 waterfalls. You'll have the entire custom-built suite to yourself with amazing views out every window. Listen to the springs pouring down the cliffside, birds chirping, and star gazing- all from your private porch. The entry is keyless for easy self-check in. We live on top of the hill and are available if you need anything.

Guest favourite
The image shows a green, grassy area with a gravel driveway curving toward a cottage surrounded by lush trees. The bright blue sky complements the verdant landscape, creating a serene outdoor setting.
Home in Whitleyville
4.92 out of 5 average rating, 181 reviews

~Liberty Cottage~ A Peaceful Getaway

This cozy cottage is the perfect get away for just you or the whole family. Relax and soak up this peaceful and scenic location.There is plenty to see, right in the back yard!!! cows, goats, chickens, and your occasional barn kitty!!! Come out, relax, enjoy family time, have a romantic getaway, unwind in one of the most beautiful scenic areas in TN. Catch a glimpse of deer as the pass through the field next to the house. Watch the birds. fiber optic internet.

Top guest favourite
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, 111 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 favourite
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, 318 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 favourite
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, 114 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!*

Top guest favourite
The cabin features a rustic wooden facade with a stone chimney, surrounded by nature. A spacious porch wraps around the structure, and vibrant trees with pink blossoms add color to the setting. The entrance is marked by a welcoming sign that reads 'Cabin by the Creek.'
Cabin in Cookeville
4.99 out of 5 average rating, 619 reviews

Cabin by the Creek

The cabin is a wonderful place for a family retreat or couples getaway! It is conveniently located 3 minutes from a four lane highway and is less than 15 minutes south of a town that has a population of around 5,000 and 20-30 minutes north of a larger college town of approximately 35,000. The Cabin is nestled by a shallow creek and faces 25 wooded acres that are ideal for hiking and enjoying nature.

Popular amenities for Tompkinsville holiday rentals

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