Holiday houses in Tompkinsville

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Tompkinsville

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

%{current} / %{total}1 / 1
Guest favourite
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, 85 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 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, 431 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 favourite
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, 372 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.

Superhost
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.
Apartment in Lebanon
4.83 out of 5 average rating, 184 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
4.92 out of 5 average rating, 306 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
An aerial view captures the modern apartment with a spacious deck, featuring outdoor seating and sleek design elements. Large windows allow for ample natural light, while the surrounding green landscape enhances the setting. The building's unique structure and elevated position are prominently displayed.
Apartment in Cookeville
4.99 out of 5 average rating, 183 reviews

Private Modern Apartment

This apartment is in the heart of downtown Algood. It is walking distance to restaurants, coffee shops, and shopping. It is less than 3 miles from downtown Cookeville including the historic West Side District, Tennessee Tech, and Cookeville Regional Hospital. The apartment is completely custom and unique in every aspect. You will have 24/7 access to the host who will go above and beyond for any need you have while still giving you complete privacy. NO PETS ALLOWED.

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, 182 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
An open living space features vaulted wood ceilings and large windows allowing ample natural light. A well-equipped kitchen with a central island is complemented by a dining area and a view of the outdoor deck. Decorative lighting enhances the inviting atmosphere.
Home in Hilham
5 out of 5 average rating, 171 reviews

Country Setting with City Comfort

Enjoy peace and quiet! The home offers many comforts and conveniences while being situated on 31 wooded acres. This is a remote, secluded location that allows you to relax, but if you do want to get out and enjoy some attractions, below are some approximate driving times. These towns offer the closest shopping so you may want to come prepared with your needs. Livingston- 25 minutes Celina- 25 minutes Gainesboro- 30 minutes Cookeville- 45 minutes

Top Guest favourite
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
4.9 out of 5 average rating, 93 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 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, 112 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.

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, 115 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, 622 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