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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Guest favourite
A hot tub is positioned outside, with its water shimmering under a soft blue light. Large windows display the interior, showcasing a colorful seating area and decorative plants, creating a harmonious connection between indoor and outdoor relaxation spaces.
Home in Clarksville
4.9 out of 5 average rating, 211 reviews

Elegant Entertainment Home The SPOT + HOT TUB

Top Reasons why you’ll love our home! We’re located in a very safe area just minutes away from many of the main attractions of Clarksville. You’ll reside in a 2,300 sqft house w/ 3 bedrooms furnished with insanely comfortable beds w 2 full bathrooms and 2 full kitchens for your convenience & space. The home sits beautifully on the edge of some of Tennessee's most beautiful trees and is also frequently visited by deer and other harmless wildlife. Grab some coffee and enjoy the morning nature view

Top Guest favourite
Cabin in McEwen
5.0 out of 5 average rating, 134 reviews

Where Thoughtful Stays Meet Peace & Nature.

Just 45 minutes from Nashville. Step into a space guests describe as tranquil, cozy, and exactly what they needed. Deer Ridge Cabin is designed for slowing down. Morning coffee on the porch, quiet evenings at the fire pit, and sightings of deer passing through the property. Guests often say it’s one of the cleanest stays they’ve experienced and that “everything has been thoughtfully prepared.” With warm details throughout, it’s a place to reconnect, recharge, and create a stay you won’t forget.

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, 365 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, 133 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, 1046 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.”

Guest favourite
A modern living area features a comfortable gray sofa paired with yellow accent pillows. A large window allows natural light, illuminating the space. A stylish kitchen showcases stainless steel appliances and dark cabinetry, with decorative items arranged on the countertop.
Condo in Clarksville
4.95 out of 5 average rating, 122 reviews

Make Lemonade in luxury w/ king bed & free parking

You will enjoy your future stylish experience at this centrally-located spacious 2 bedroom, 2.5 bath condo located in Sango, TN near I-24 and approximately 40 minutes from Nashville. Welcome to Make Lemonade where you let our hair down, relax, and leave our worries at the front door. You'll experience peace, joy, and sheer bliss at our brand new condo. you'll look forward to your stay and feeling right at home while making lemonade. You message me for military and extended stay discounts.

Top Guest favourite
A cozy living room features two soft sofas arranged around a round coffee table. A stone fireplace serves as a focal point, while large windows allow natural light and offer views of the surrounding landscape. A dining table with white chairs completes the inviting space.
Cabin in Pleasant View
5.0 out of 5 average rating, 111 reviews

Storybook Cabin Near Nashville

Enjoy a secluded retreat at The Feathered Nest, a charming log cabin just 20 minutes shy from Downtown Nashville. Built in 1979 and situated on 15 acres of land, this traditional wood cabin provides a private oasis with sprawling views of green pastures. Surround yourself with the quaint country atmosphere without being too distant from the center of Nashville. Access to grocery stores and lovely local shops are just a 5-minute drive away. A haven for those who are seeking quiet solitude.

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, 441 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, 293 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, 431 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, 344 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.

Guest favourite
The outdoor space features a well-lit area with a hot tub, a wooden deck, and a swing set. Surrounding greenery adds to the natural setting, while a cozy structure is visible to the right, and a spacious lawn extends to the horizon under a colorful sky.
Barn in Pleasant View
4.96 out of 5 average rating, 100 reviews

*Private 2 Acres!* | Hot Tub | 20 Min to Nash!

Imagine sipping your wine in the hot tub as the sun sets over the rustic Tennessee Tobacco barn on the horizon. Imagine enjoying 2 acres of the country all to yourself, then popping in your car and hitting Broadway in 25 min. Imagine having a private retreat to enjoy quality time with your significant other just outside the city. If you want a retreat that is convenient to the city, the Guest Barn is for you!

Popular amenities for Southside holiday rentals