Holiday houses in Southside

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Southside

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

%{current} / %{total}1 / 1
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, 436 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
Cottage in Ashland City
4.92 out of 5 average rating, 113 reviews

The Little House by the Woods

Hunt, Hike & More! A tranquil retreat with all the comforts of home. Calming colors, lots of natural light. Enjoy Tennessee's natural beauty with a subtle homage to our favorite Gulf Coast beaches. "The Little House by the Woods" is on a ridge surrounded by trees. Across the road is Cheatham Wildlife Management Area with 20,000 acres of hill country with hiking, hunting and birdwatching. You'll have easy access to so many parks, recreation and all that Nashville (30 min. away) has to offer.

Guest favourite
Home in Clarksville
4.93 out of 5 average rating, 204 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.

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, 123 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
4.99 out of 5 average rating, 1,020 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 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
5 out of 5 average rating, 211 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 favourite
Cabin in Kingston Springs
4.97 out of 5 average rating, 126 reviews

Peaceful Rustic Cabin- Nature's Retreat for All

Welcome to the Eagles Rest! A unique 960 sq ft rustic cabin that rests on over 2 wooded acres in a peaceful and beautiful rural setting that can be hiked down to a creek on the property. This is the ideal spot for couples, outdoor lovers and those who simply want to recharge from the daily hustle and bustle. We are minutes away from outdoor activities such as kayaking, fishing, disc golf course, hiking, and much more. We are also a short 30 minute drive to Nashville and Franklin.

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, 403 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
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, 406 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
Cabin in McEwen
5 out of 5 average rating, 126 reviews

Peaceful Cabin + Deer | Cozy & Spotless | Retreat

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 just 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 cottage nestled among tall trees is captured in warm sunlight. The exterior features a blend of brown siding and stone accents. A covered porch extends from the front of the house, inviting visitors to enjoy the view of the surrounding nature.
Cottage in White Bluff
4.97 out of 5 average rating, 210 reviews

River Roost

A unique place located minutes from the "Narrows of the Harpeth" State Park. Canoeing, kayaking, hiking. and zip lining all just less than one mile away. If you need more space, check out the "Nest". Just steps away from the "River Roost", a separate private entrance offers a comfy couples space. See our separate listing. Our goal is to provide a private, safe, and comfortable space for all our guests. Please see our house rules regarding guest limits and visitors.

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, 317 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

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