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 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!

Top guest favorite

A rustic cabin is framed by lush greenery, featuring a welcoming porch adorned with hanging plants. The green metal roof complements the warm wood exterior, while a meticulously landscaped garden with vibrant flowers enhances the inviting atmosphere.

Cabin in Tompkinsville

5 out of 5 average rating, 31 reviews

Pine Grove BNB

Located minutes from the heart of Tompkinsville, experience the charm of our renovated, early 1900's cabin that is professionally landscaped with ambient outdoor lighting. You'll feel miles away nestled among a historic pine grove overlooking more than 100 acres. A respite for those looking for adventure and R&R alike, we welcome anyone in search of a creative getaway, restorative time for themselves, & those wanting to escape to a curated & welcoming space to find a little peace & clarity.

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 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

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, 165 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

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.

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

4.98 out of 5 average rating, 598 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.