Holiday houses in Southside

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Top-rated holiday rentals in Southside

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A bright living area is showcased, featuring a dining table with six white chairs and a spacious sofa set. Natural light filters through the windows, illuminating an artwork on the wall. A ceiling fan and a cozy area rug contribute to the welcoming atmosphere.
Townhouse in Clarksville
4.95 out of 5 average rating, 310 reviews

Downtown Luxury 2Bedroom Townhome

Relax in this stylish, sun-filled Town home, just a hop, skip, and jump from everywhere you want to be. Enjoy your morning coffee on your private patio surrounded by Tennessee lush green trees. Located in the heart of downtown Clarksville, is just a short walk to shops, restaurants, live theater, Austin Peay State University, and the River Walk. 5 minute walk to Downtown Clarksville 45 minutes to Nashville 20 minutes to Fort Campbell Check out our other listings by clicking on our host profile.

Top Guest favourite
A charming tiny house is nestled among lush trees, featuring a welcoming front porch with seating. Large windows allow natural light to flood the interior space, while a covered area provides shelter for enjoying the outdoors. The exterior is complemented by a simple, unobtrusive color palette.
Tiny home in Pegram
4.98 out of 5 average rating, 451 reviews

Little House in the Woods

This oasis in the trees is waiting to help you escape, renew and rejuvenate! Located on over thirteen acres of beautiful woods, bordered by a spring-fed creek, it’s a great place to stay in or get out and explore. We love to offer our guests not only a great place to stay but an experience they will talk about for years to come. We love providing lots of little extras to help make your time here really special. This is the perfect spot for a romantic getaway, family fun vacation, or solo retreat

Top Guest favourite
The charming cottage entrance features a welcoming porch with a ceiling fan and soft lighting. Stairs lead up to the door, surrounded by neatly trimmed greenery and potted plants. An American flag is displayed on one side, enhancing the inviting ambiance.
Tiny home in Dover
5 out of 5 average rating, 118 reviews

Tiny Home, river view, boat parking, & hot tub.

Welcome to Cottage on the Cumberland – where nature's embrace meets modern comfort! You can disconnect from and find yourself in an unforgettable lakefront experience. With LBL, KY Lake, Lake Barkley, & Ft. Donelson minutes away, you're in the heart of recreational paradise. So, whether it's fishing, hunting, boating, ATV’s, horseback riding, hiking, or just enjoying the beauty of nature, come & experience tranquility & adventure all together! Please read hot tub info in “Other Details to Note”.

Top Guest favourite
An airy kitchen and dining area features wood cabinetry and a spacious table surrounded by rustic chairs. Large windows allow natural light to fill the space, while high ceilings enhance the openness. A cozy seating area is visible near the door, inviting relaxation.
Cabin in Cumberland Furnace
4.97 out of 5 average rating, 35 reviews

~The Laramie~ A cozy Log Cabin rustic plus comfort

Conveniently located 1 hr to Nashville 30 mins to Clarksville 5 miles north of Charlotte Log Cabin where you can come to relax Privacy fence around (since photos) large deck, nice front porch, fire pit, come make memories! We are ok with pets (OUTSIDE ONLY) if you clean up behind them. 2 bedrooms, each with queen bed 2 full baths 1 day bed in balcony Lovely wood paneling interior with vaulted ceiling, full kitchen, very comfy! ~Good location for multiple wedding venues in the area

Top Guest favourite
A charming treehouse is elevated among tall trees, surrounded by lush greenery. The wooden structure features large windows offering views of the forest, and a spacious deck extends outward for outdoor enjoyment.
Treehouse in Pegram
4.91 out of 5 average rating, 363 reviews

Private Treehouse Escape Minutes from Downtown

Connect with nature at this unforgettable escape in Nashville's backyard. This treehouse is nestled in a Tennessee hardwood forest in a hollow. Close to the city, but away from it all, it's a perfect place to retreat from normal life. This isn't a tree fort. It's a tiny house with a loft in the trees over a trickling spring fed creek. It's private with all windows facing the forest. All the fun of being a kid w/ comforts of home like toilet, ac, electric fireplace, heater & 3 season hot shower.

Top Guest favourite
A tranquil sunset sky is displayed with colorful clouds in shades of pink and blue. The tiny house is seen on the right, featuring a porch and a small wooden privacy screen. The surrounding area is lush with green trees and an expansive grassy space.
Home in Southside
4.99 out of 5 average rating, 131 reviews

Paradise Hill Tiny House

Relax in this calm, stylish space. Come enjoy your stay at our small, quaint, inviting tiny house located in a peaceful country setting. Property is very close to the Historic Southside Market, Historic Collinsville and a short drive to beautiful Charlotte, TN where you can shop their unique variety of farm to table and craft stores. Only 14 miles to Clarksville, TN, 26 miles to Dickson, TN and 42 miles to Nashville! Come relax in the country and soak in the beauty and peacefulness of it all!

Top Guest favourite
The entrance to Wee Nook is framed by lush greenery, with a curved roof and a wooden door. A stone pathway leads to a pavilion, offering outdoor seating among the surrounding trees. The natural setting provides a peaceful ambiance in the woods.
Earthen home in McEwen
4.98 out of 5 average rating, 1,046 reviews

Wee Nook- a Hobbit Hole

Wee Nook is a 360 square foot living space with a full kitchen and bathroom. It is tucked underground in the middle of the woods. Please come enjoy the woods, farm animals, trails, pond and wide open space while you're here! As JRR Tolkien said: “In a hole in the ground there lived a hobbit. Not a nasty, dirty, wet hole, filled with the ends of worms and an oozy smell, nor yet a dry, bare, sandy hole with nothing in it to sit down on or to eat: it was a hobbit-hold, and that means comfort.”

Top Guest favourite
A charming cabin is framed by lush greenery and towering trees, featuring a rustic wooden facade and a blue metal roof. The entrance is marked by a simple door surrounded by vibrant bushes and plants, set against a backdrop of soft, sunlit grass.
Cabin in Fairview
4.98 out of 5 average rating, 210 reviews

Whispering Waters Cabin by the Creek

Whispering Waters offers a quiet space to relax and enjoy your time spent away from home. It is a four room cabin adjacent to Caney Fork Creek, which feeds into the South Harpeth River in Fernvale. The cabin easily hosts four guests. The queen size bed is complimented by a sleeper sofa in the living room, which sleeps two as well. It's an intimate space located in a lovely setting. IF you are booking "same day" please give me a call so I can make any necessary last minute arrangements.

Top Guest favourite
A cozy cabin is nestled among lush greenery, partially obscured by mature trees. A gravel path leads to the entrance, which is flanked by wooden accents. A small outdoor seating area is visible, enhancing the connection to the serene natural surroundings.
Cabin in Chapmansboro
4.96 out of 5 average rating, 438 reviews

White Duck

Keep it simple at this peaceful and centrally-located cabin minutes from Interstate 24. Twenty minutes from Clarksville, APSU and nearby Fort Campbell KY to the north and thirty minutes from downtown Nashville and all it has to offer to the south. The quiet woodsy setting and comfortable interior of White Duck provide a restful transition from a day of sightseeing or an exciting football or hockey game. **There is a $50 pet fee** Please include your pet during the booking process.

Top Guest favourite
A charming cabin is set amidst a lush, wooded landscape. The structure features a bold red roof and wooden exterior, surrounded by trees and a gravel path leading to the entrance. Natural greenery enhances the serene atmosphere of the secluded property.
Cabin in Kingston Springs
4.97 out of 5 average rating, 290 reviews

King Bed, Cabin in Woods with Spring-fed Stream

This cozy little cabin nestled in the trees is located in a rural neighborhood and sits 150ft away from the street. The cabin sits on 3+acres. Enjoy a short hike to the spring-fed stream on the property. 35 minutes to downtown Nashville. Cal-King Premium Nectar Mattress, and 2 full sized floor mattresses. Enjoy nature as you sit around the fire pit or play horseshoes, creating a relaxing getaway with the beauty Tennessee has to offer! Dogs are welcome (50lb limit, max of 2).

Top Guest favourite
The Bridge House is seen suspended over a serene creek, framed by lush greenery. A calm water surface reflects the building and surrounding foliage. A gray dog stands on a rock in the foreground, appearing to enjoy the natural setting.
Place to stay in Ashland City
4.97 out of 5 average rating, 429 reviews

Bridge House over Blue Springs Creek

Magical in all seasons! Soothe your soul with an unforgettable escape, surrounded by nature and suspended twenty feet above a babbling brook! Listen to the rushing water and the bamboo whispering in the breeze, take in a sunset, or wade in the creek below. We hope you’ll enjoy this unique covered bridge conversion, expanding from bank to bank with a 50-foot front deck. Breakfast provided the first day includes fresh fruit, a half dozen eggs, and muffins, coffee and tea.

Top Guest favourite
A charming treehouse is nestled among tall trees, featuring earthy wooden tones and a rustic design. Soft outdoor lighting creates a cozy ambiance, while a path made of stones leads to the entrance. The treehouse is elevated, providing a unique vantage point into the surrounding nature.
Treehouse in Greenbrier
4.98 out of 5 average rating, 340 reviews

Nashville Luxury Dream Treehouse +Spa

This beautifully designed and luxurious treehouse sits on a ridge overlooking our creek. With only a 25min drive to downtown Nashville, you are tucked away amidst the towering hardwoods-away from the city noise. With careful attention to detail, the treehouse decor and design is meticulously curated to create an atmosphere of rest and beauty. This space is ideal for a couple, but can sleep four (twin beds in the loft). Parties are not permitted on the premises.

Popular amenities for Southside holiday rentals