Holiday houses in Tompkinsville

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Top-rated holiday rentals in Tompkinsville

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Top Guest favourite
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, 156 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 favourite
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 favourite
A hot tub is situated on a deck, surrounded by trees. The bubbling water can be seen, while a pair of bare feet rests on the edge. Soft light filters through the foliage, creating a serene atmosphere.
Cabin in Hilham
4.98 out of 5 average rating, 279 reviews

#3 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 favourite
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, 438 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 favourite
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, 533 reviews

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

Perched 15 feet up in the Tennessee woods, The Treehouse is where you come to celebrate something — an anniversary, a proposal, a birthday, or just the fact that you finally stopped. Hand-built by Amish craftsmen with an 1848 front door and 100-year-old stained glass, it pairs a cast iron claw-foot tub for two, a king bed, and a private hot tub under the stars with full access to a sauna, cold plunge, and more. 1 hour from Nashville, 15 minutes from Cookeville. Just far enough to feel gone.

Top Guest favourite
The spacious living room features warm wood paneling and high ceilings, complemented by a large, plush sofa and loveseat. A coffee table centers the area, while a smart TV and decorative accents enhance the cozy ambiance. Natural light enters through multiple windows with simple coverings.
Cabin in Scottsville
5 out of 5 average rating, 120 reviews

Liberty Hills Cabin | Hot Tub | Fire Pit

Welcome to our cozy cabin on our picturesque 146-acre farm! Escape to a beautifully remodeled cabin that is nestled within the rolling hills of a cattle farm. It boasts panoramic views from its front and back porches. Whether you just want to relax and enjoy the quaint, peaceful, country setting or explore nearby attractions, this 2023 renovated cabin is your perfect retreat. Conveniently located just 10 min from Scottsville, 15 min from Bowling Green, and 15 min from Barren River Lake.

Top Guest favourite
A rustic cabin exterior features dark wooden siding and a welcoming porch area. A wooden railing surrounds the entrance, while stone stepping stones lead through a grassy yard. A metal roof adds a touch of character, complemented by nearby greenery.
Cabin in Edmonton
5 out of 5 average rating, 116 reviews

Secluded Cabin with private 3 acre fishing lake

Very secluded cabin on dead end road, gated with keypad entrance. Three acre stock fishing lake .Fishing is catch and release only.Aluminum boat available for guest use.Wildlife feeder. Walking trails but not for the faint at heart . Outside fire pit with wood supplied.Charcoal grill on site with farmhouse style outside table . Owner is on-sight , separate residence.Not handicap accessible.

Top Guest favourite
Guesthouse in Lafayette
4.99 out of 5 average rating, 101 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.

Top Guest favourite
Guest suite in Cookeville
4.99 out of 5 average rating, 230 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 favourite
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 favourite
A dining area is showcased, featuring a round wooden table surrounded by two chairs. Natural light streams through a window above the table, with a vintage cupboard and decorative items lining the walls. The ceiling displays corrugated metal, adding character to the space.
Place to stay in Alvaton
4.98 out of 5 average rating, 521 reviews

studio apt w/bridge o/gorge, deck, view of woods

750 sq ft studio apt with covered breakfast deck with steps to a swinging bridge and woods. Mown paths meander thru this 230-acre farm for exploring by foot or driving the 4-seater golf cart provided. Private yet accessible. Loft has king bed. Main floor living area queen sofa bed. Barn loft/party room at entry is complete with piano and double futon for the hardy campers. Covid19 cleaning standards; CCPC license #WC0026

Top Guest favourite
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, 117 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.

Popular amenities for Tompkinsville holiday rentals

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