Vacation rentals in Southside

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Top-rated vacation rentals in Southside

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Top guest favorite
A studio loft features charming brick walls and bright windows that allow natural light to fill the space. A spacious bed is positioned beside a comfortable sectional sofa. A media console and decorative accents enhance the cozy atmosphere, creating a welcoming environment.
Loft in Clarksville
4.97 out of 5 average rating, 170 reviews

A cozy studio apartment downtown Clarksville

The allée des fraises loft is a studio loft inspired by my stay in Paris and London, located on the second floor of an historic 1890’s building. The charming brick walls and rustic aesthetics add character to this bright space. Perfect for a couple’s getaway or a solo traveler in town for work. Walking distance to coffee shops, restaurants, local cafes, boutiques, breweries and more. Near Austin Peay State University, Fort Campbell and less than hour from Nashville. A parking pass is provided.

Superhost
An outdoor seating area features a comfortable light-colored sofa adorned with a decorative pillow. A dark tabletop with a circular opening is positioned in the center. Two wooden rocking chairs are visible in the background, set against a brick wall.
Home in Clarksville
4.93 out of 5 average rating, 174 reviews

Historic Downtown cottage FULL of Amenities

Take a break and unwind at this peaceful guest cottage located on historic Greenwood Ave. 1 mile from downtown and APSU, this quaint home is full of amenities and waiting for you! Enjoy cooking in the equipped kitchen,dine in front of the electric fireplace with remote settings. Plenty of games and Roku TV to pass your time. The queen bedroom is ideal for 2 adults while the living room has 2 twin ottoman beds available for kids. Full bath, laundry room, and a desk for the working professional.

Guest favorite
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
4.9 out of 5 average rating, 313 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.

Guest favorite
An aerial view showcases the tranquil landscape of the Cumberland River, bordered by lush greenery and wooded areas. The river meanders through the scene, with gentle curves leading to calm water and a natural shoreline, inviting exploration and outdoor activities.
Cottage in Dover
4.94 out of 5 average rating, 145 reviews

Cozy Pet-Friendly Riverfront Cottage

Welcome to The Mallard House. A cozy cottage overlooking the Cumberland River. Bring the dogs and relax on the wrap-around porch. We offer all the kitchen tools to cook a delicious meal and enjoy the peace and quiet of the country. The Mallard house is conveniently located 15 minutes from the quaint town of Dover where you can find all the necessities. Nashville is 1.5 hours for those wanting a day trip to the city and Land Between the Lakes is 20 minutes for those seeking outdoor adventures!

Top guest favorite
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, 100 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 favorite
A cozy living area features a soft, neutral sectional sofa adorned with patterned cushions and a warm throw. A round wooden coffee table sits in the center, while colorful wall art adds a touch of character. A hanging chair provides an inviting seating option.
Townhouse in Clarksville
5 out of 5 average rating, 135 reviews

TOP 1% w/ King Bed! Cozy&Luxury Downtown Townhome

"Sunjoo's Place on Cigar Hill," Hosted by Byers & Harvey is a 2 BR/2.5 BA with a big bonus room in downtown! The MB has a king bed and ensuite with double vanity and tile shower. 2nd room has a queen bed and ensuite. Downstairs, you can find designated office/perfect kids hang out bonus room with big desk and trundle bed with 2 twin size mattress. However, there is NO bathroom and NO window in the basement. Up to 6 people (max 4 adults) can stay comfortably. Inquire about long-term stays!

Top guest favorite
A contemporary living room is highlighted by a large mirror and stylish light fixture. A comfortable gray sofa with colorful throw pillows is positioned near a wooden coffee table. A vibrant area rug complements the hardwood floor, while a flat-screen television is mounted on the wall.
Apartment in Clarksville
4.99 out of 5 average rating, 172 reviews

2 Bedroom Hidden Gem, Downtown Clarksville

Kick back and relax in this calm, stylish space. This is a charming home nestled in the heart of Clarksville! This cozy Airbnb is the perfect choice for your stay in the vibrant city of Clarksville. As you step inside, you'll be greeted by a warm and inviting atmosphere. The living room is tastefully furnished, providing a comfortable space for relaxation and entertainment. Whether you're visiting for business or pleasure, this is the perfect home away from home. Book your stay today!

Top guest favorite
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, 346 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.

Guest favorite
Apartment in Clarksville
4.9 out of 5 average rating, 125 reviews

Serene private new construction walk out apartment

Beautiful 1 bed 1 bath apartment tucked into the woods in Cumberland Heights. Enjoy a private getaway but still convenient access to all that Clarksville has to offer. Close to Austin Peay State University, 10 minutes from downtown and 30 minutes from Fort Campbell. The Space: Comfortable queen bed with full bath (shower only-no tub). Private entrance to walkout basement apartment. No access to main house from apartment. Full kitchen with coffee provided.

Guest favorite
A charming lighthouse stands nestled among trees as dusk approaches, with its light gently shining. Surrounding greenery and a swing set frame the scene, demonstrating a tranquil outdoor space that invites exploration.
Lighthouse in Clarksville
4.83 out of 5 average rating, 123 reviews

Lighthouse of the Mid-South

Recently remodeled! New second story addition! An Amish built lighthouse that has been furnished and is tucked away in the county but only 15 min from downtown and APSU. The heating and cooling is an in-wall unit as well as a space heater. It's situated on a pond across a foot bridge from the barn. Behind is 4 acres of trees with trails through it that run up to a cattle pasture. There is plenty of space to roam with a play set to entertain the kids.

Top guest favorite
A spacious country home is set among lush green trees, with well-maintained grass surrounding the property. The blue sky provides a bright backdrop, while large windows reflect natural light. The inviting entrance features a pathway leading to the house.
Guest suite in Dickson
4.98 out of 5 average rating, 175 reviews

Country Penthouse

Skip the same old hotel experience and escape the Country Penthouse. The Country Penthouse is set in the beautiful Tennessee countryside amongst the trees. Watch as the sunrises over the tree tops from the private deck and the sunset from the private balcony. Hear the sounds of nature and the birds singing. Let time slip away as you relax and unwind. Enjoy the the wide open spaces away from the hustle and bustle of the city.

Top guest favorite
Cabin in McEwen
5 out of 5 average rating, 114 reviews

Find your tranquility at Deer Ridge Cabin.

During our travels, we’ve stayed in countless hotels, motels, cabins, and even tents. It is our opinion that this guest cabin is by far the most well appointed, cozy and peaceful place to rest one’s travel weary body or take a break from the hustle and bustle. These are the things we look for in a memorable stay. We sincerely hope you do as well. Please enjoy your stay at the Deer Ridge Cabin.

Popular amenities for Southside vacation rentals

  1. Airbnb
  2. United States
  3. Tennessee
  4. Montgomery County
  5. Southside