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
4.93 out of 5 average rating, 144 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, 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 favorite
A well-maintained brick house is set on a grassy lot, featuring multiple windows that provide ample natural light. The front porch is accessible, and a lightly sloped paved path leads to the entrance. Mature trees are visible in the surrounding area.
Home in Glasgow
4.98 out of 5 average rating, 347 reviews

The Belk House near Mammoth Cave

This house is located on a well known street 8 blocks from downtown Glasgow, KY. We are eleven miles from I-65 and 90 miles from either Louisville or Nashville. Conveniently located amid the medical community of Glasgow; five blocks from T J Samson Hospital and the Shanti Niketan Hospice Center. For tourism, located 30 minutes from Mammoth Cave National Park; 20 minutes from Barren River State Park; 40 minutes from National Corvette Museum; and 45 minutes from the Abraham Lincoln Birthplace

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, 428 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
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, 370 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
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, 305 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, 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 favorite
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 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, 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 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, 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 favorite
A single-story home is set among lush green trees, featuring a metal roof and light blue siding. Windows are framed in burgundy, providing a contrast to the exterior. A gravel area surrounds the house, with wooden logs placed in the foreground, enhancing its secluded setting.
Cabin in Celina
4.93 out of 5 average rating, 109 reviews

Private getaway in the hills of Dale Hollow

Completely renovated, secluded home in the quiet hills of Dale Hollow. Perfect getaway for fishing, horseback riding, other water activities, or just to get away for some peace and quiet. Nearest marina is Holly Creek, just minutes away with multiple other options in the area. Close to horse trails and downtown Celina is a 10-15 minute drive with grocery stores, antique shops, and local restaurants.

Superhost
A charming house is surrounded by greenery, featuring a spacious porch that extends across the front. Large windows allow natural light to enter the interior. The driveway is paved, leading to a tranquil outdoor space with abundant trees and shrubs in the background.
Home in Livingston
4.81 out of 5 average rating, 166 reviews

Cabin-Inspired Studio

Keep it simple at this peaceful and centrally-located home. Studio floor plan offers a wide open spatial experience in a quiet suburban setting. We are only 3 mins from downtown shopping, attractions, and historical landmarks. Lake access is only a short drive away. Great location and dwelling for a short stay while travelling or longer vacation plans! Come enjoy Overton County with us!!!

Popular amenities for Tompkinsville vacation rentals

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