Vacation rentals in Tompkinsville

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Top-rated vacation rentals in Tompkinsville

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Top guest favorite

The rooftop balcony features a spacious wooden deck, furnished with a lounge seating area and a long dining table. The space is surrounded by a black railing, providing views of the neighborhood and ample room for outdoor gatherings.

Loft in Glasgow

5 out of 5 average rating, 99 reviews

Balcony on Broadway - Enjoy historic Glasgow!

New life to an old building! Beautiful hardwood floors, exposed brick walls, large windows for daytime views, blackout shades for sound sleeping and a stunning rooftop balcony for relaxing or playing games with family and friends. Enjoy a live show at Glasgow's Historic Plaza right outside your window. Walk to local restaurants, shops, Cultural Center, hear local music, visit our farmer's market, attend a church service, enjoy the church bells. We hope you choose to enjoy your visit with us!

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

4.93 out of 5 average rating, 245 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, 340 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 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, 404 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, 407 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 tiny guest home is featured with a welcoming front porch. A simple chair is positioned beside the entrance, which is framed by a decorative wreath. The home is light-colored with green accents, set against a backdrop of rolling hills.

Guesthouse in Scottsville

4.98 out of 5 average rating, 247 reviews

Adorable Guesthouse #2 Close to Barren River Lake

We are excited to present our tiny guest home #2. Perfect for the fisherman or couple wanting to stay close to Barren River Lake or Mammoth Cave. This unit is centrally located between several towns and less that four miles from Port Oliver Boat Ramp and Dam. It is close to the main house so we will be available if you need anything. Peaceful surroundings, comfortable queen bed, refrigerator, microwave and coffee bar. 55" smart tv to kick back & relax with. Exterior outlet for boat.

Guest favorite

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, 295 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

A spacious Jacuzzi bathtub is filled with bubbles, positioned near a large window that frames a view of green trees and natural landscaping. Soft candlelight enhances the serene atmosphere, while relaxation is emphasized by the peaceful setting.

Guesthouse in Pleasant Shade

4.83 out of 5 average rating, 259 reviews

“Alice's Cottage”

Come experience the Magic of Wonderland! You’re going to love this one of a kind, full room service, spa bath house style cottage tucked deep within the mountains of Tennessee. Escape reality in our Alice in Wonderland themed Retreat! We offer a full Menu of affordable relaxing services including breakfast, lunch, dinner, and desserts. Spoil yourselves this getaway with the Royal treatment. Get ready to relax, unwind and be pampered like the King & Queen of Hearts!

Top guest favorite

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, 200 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 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, 178 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.

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, 107 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

4.92 out of 5 average rating, 106 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.