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, 100 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!

Top guest favorite

A charming treehouse design is perched above the forest floor, featuring large windows that invite natural light. A spacious deck with a railing extends from the structure, and wooden stairs lead down to a gravel area with stacked firewood nearby. The surrounding trees create a secluded setting.

Treehouse in Franklin

4.99 out of 5 average rating, 117 reviews

Treetop Views *Trails, Fishing *No Cleaning Fee

Amazing two-story house nestled high up in the trees. A true treehouse! This treehouse sits amongst a forest of poplar trees and feels very secluded and private. It has spectacular views of Kentucky’s rolling hills as it looks out across the valley. This treehouse was hand built and handcrafted with love and attention to detail. Located just off of I65 outside the historical little town of Franklin, KY. We are located between Nashville (45min), Bowling Green (35min) and Mammoth Cave (55 min).

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, 409 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 favorite

A modern kitchen features dark cabinetry, white subway tile backsplash, and stainless steel appliances. A spacious wooden island provides seating for four with woven stools. Natural light floods in through large windows, highlighting the warm reclaimed wood flooring and vaulted ceiling with rustic beams.

Farm stay in Scottsville

4.98 out of 5 average rating, 257 reviews

Flower Farm Modern Loft Retreat - Mammoth Cave

Peaceful privacy on our 227 acre farm, convenient to Bowling Green, Mammoth Cave, and Barren River Lake. The 900 sq ft loft above our home’s garage has private exterior entrance to the finished modern farmhouse loft with completely separate ductwork and HVAC system. The loft features everything you need to stay at the farm and relax: high end, furnished kitchen to cook meals in & fiber optic internet to work or stream. Adirondack chairs and a propane fire pit make for wonderful stargazing.

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, 365 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.

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, 253 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.

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, 265 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"

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

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.

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, 308 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, 110 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!*

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, 107 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.