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
4.94 out of 5 average rating, 154 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
Cabin in Hilham
4.97 out of 5 average rating, 321 reviews

#2 Talley's Cabins by Dale Hollow Lake

Welcome to Talley’s Cabins near beautiful Dale Hollow Lake nestled in the Upper Cumberland area of TN. A quiet, peaceful and clean stay in the beautiful hilltops. With 47 acres to enjoy including hiking trails, scenic grounds to snap a picture, your own hot tub and fire pit. We are also just a short drive to some great attractions such as: Cummins Falls State Park, Standing Stone State Park, and numerous marinas surrounding the beautiful No. 1 Houseboat Lake on the Continent, Dale Hollow.

Top guest favorite
Barn in Austin
4.98 out of 5 average rating, 410 reviews

Unique & Authentic Farm Stay 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, 436 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 unique treehouse structure is viewed among vibrant autumn foliage. The design features large glass panels allowing natural light to flood in. A stone patio surrounds a fire pit with seating, while a hammock is visible nearby, inviting relaxation in the serene forest setting.
Treehouse in Bloomington Springs
4.98 out of 5 average rating, 532 reviews

Romantic Treehouse w/ Sauna, Hot Tub, & Fire Pits!

Unplug at The Treehouse at Hideout Hotels! Perched 15 feet above the forest floor, The Treehouse offers a private, romantic retreat to relax & immerse yourself in a serene forest escape. We’re located 1 hour from Nashville, TN, & 15 minutes from Cookeville, TN. Shared Property Amenities - 8-Person Barrel Sauna - Cold Plunge - Outdoor Kitchen w/ Grill & Pizza Maker - Golf Chipping & Putting Green - Pickleball & Basketball Court - Shasta Camper Library & Store - Outdoor Shower - Gas Fire Pit

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, 277 reviews

Page's Legacy: Spring Getaway at the Lake

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"

Top guest favorite
Guesthouse in Lafayette
4.99 out of 5 average rating, 100 reviews

The Upper Room

**We are still cleaning up debris from 2026 Snowmageddon! 😆 Be patient! Welcome to the Upper Room, a studio apartment above our detached garage with one bedroom/one bath, and small kitchen. Smart TVs w/ Roku. Conveniently located on Hwy 52 between Westmoreland and Lafayette, with a short drive of 5-10 minutes to either. If you are in town for a wedding, revival, hiking or funeral, give us a try. Winding Stairs is five minutes away and Dollar General is 4 minutes down the road.

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, 186 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
A well-equipped kitchen features wooden cabinetry and modern appliances. A dining table made of natural wood is set in the center, surrounded by chairs. A cozy sitting area is positioned along the wall, with a staircase leading to a loft space above, under wooden beams.
Cabin in Bowling Green
4.99 out of 5 average rating, 231 reviews

Tiny Cabin in the woods!

Tiny cabin in the woods about 30 minutes from Mammoth Cave, and 20 minutes from WKU, Historic Downtown Bowling Green, Beech Bend Raceway and the National Corvette Museum! You will enjoy a peaceful setting hidden in the trees, a fully-stocked kitchen, Fiber Wi-Fi, hot tub and fire pit. Enjoy picking blackberries late June and July! Need more space? Check out our other listing with additional sleep space: https://www.airbnb.com/slink/Cor5Q5Gm

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, 115 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.

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, 322 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!

Popular amenities for Tompkinsville vacation rentals

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  4. Monroe County
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