Vacation rentals in Tompkinsville

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Top-rated vacation rentals in Tompkinsville

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Top guest favorite
An outdoor seating area features two wooden adirondack chairs positioned beside a stone fireplace, where a welcoming fire is lit. Warm lighting highlights the wooden deck, and a small circular table rests nearby. A stack of firewood is neatly arranged against the wall.
Cabin in Jamestown
4.95 out of 5 average rating, 129 reviews

River Loft Cabin w Free Kayaks

* Waterfront cabin overlooking the lake. * Free kayaks: Kayak # 1: double sit-on-top ocean kayak. Kayak #2: single Pescador kayak. * Launch the Kayaks from the bottom of our ridge. * For boats: the boat ramp is 1/4 mile on Riverton Rd. * Wood burning outdoor fireplace on the open deck. Enjoy one of the 3 decks. Inside: * 3 queen beds, 1 bathroom, Central AC and heat, fresh bedding and towels, equipped kitchen. * Excellent WiFi at the cabin but cell service is spotty. Use WiFi calling.

Top guest favorite
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, 247 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 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
4.96 out of 5 average rating, 76 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 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, 407 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 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, 412 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!

Top guest favorite
The spacious living room features warm wood paneling and high ceilings, complemented by a large, plush sofa and loveseat. A coffee table centers the area, while a smart TV and decorative accents enhance the cozy ambiance. Natural light enters through multiple windows with simple coverings.
Cabin in Scottsville
5 out of 5 average rating, 100 reviews

Liberty Hills Cabin | Hot Tub | Fire Pit

Welcome to our cozy cabin on our picturesque 146-acre farm! Escape to a beautifully remodeled cabin that is nestled within the rolling hills of a cattle farm. It boasts panoramic views from its front and back porches. Whether you just want to relax and enjoy the quaint, peaceful, country setting or explore nearby attractions, this 2023 renovated cabin is your perfect retreat. Conveniently located just 10 min from Scottsville, 15 min from Bowling Green, and 15 min from Barren River Lake.

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
4.97 out of 5 average rating, 267 reviews

Page's Legacy: Favorite Fall Getaway

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"

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, 296 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.

Guest favorite
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, 179 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 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, 310 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!

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
4.97 out of 5 average rating, 111 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 favorite
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, 603 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 vacation rentals

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