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Vacation rentals in Southside

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Southside

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

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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 homes in Pegram
4.98 out of 5 average rating, 432 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
A single-story house is surrounded by trees, featuring a large deck with seating. Natural light highlights the exterior's soft gray siding and a central chimney. A pathway leads to the entrance, creating a welcoming connection to the spacious outdoor area.
Cottage in Ashland City
4.92 out of 5 average rating, 111 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
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, 203 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.

Superhost
The exterior of a black cabin is shown, featuring large glass doors that provide views into the interior. Surrounding trees create a natural backdrop, and a gravel pathway leads to a fenced entrance. Outdoor lights are visible, enhancing the welcoming feel of the space.
Cabin in Joelton
4.83 out of 5 average rating, 250 reviews

Tennessee Mountain Home | w/ SPA

Inspired by Dolly Parton's Tennessee Mountain Home, our cabin is nested 20 min from the heart of Nashville on 4 acres of secluded woods. Our cabin takes you back in time with the comforts of beautiful quilts, handcrafted pottery and authentic hardwood floors. Sit in the hot tub and see the stars thru a canopy of trees or listen to Dolly's old records on the patio. Whether you are planning a romantic weekend, holiday w/ family or a girls trip, our Tennessee Mountain Home is your perfect getaway.

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, 121 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
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, 209 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, 124 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, 399 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, 403 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, 316 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
A unique structure resembling a boat stands on a grassy hillside, surrounded by trees. A wooden deck encircles the building, featuring round windows along its exterior. The rustic design and red metal roof complement the natural landscape.
Boat in Springfield
4.94 out of 5 average rating, 392 reviews

Sheet

Welcome to Kelly’s Jubilee. Look us up online for a discount and more information on our romantic and birthday packages. The ark was featured in Southern Living magazine and Tennessee Crossroads. (A travel show) and recently HGTV Airbnb is having technical problems and no longer offers any kind of support for its hosts. I’m sorry if the calendar says not updated. Please try the website or contact me the number is listed on the Kelly’s Jubilee website.

Superhost
Cabin in White Bluff
4.94 out of 5 average rating, 155 reviews

The Lodge at Oak Haven Farms - Outside Nashville

Perfect way to get away & unplug while being nearby. Close enough to Nashville to enjoy everything it has to offer yet total seclusion for peace and quiet in a one of a kind cabin experience on a beautiful wooded property near Montgomery Bell State Park. Loft up top with full-size bed and bunk beds downstairs with wooded views no matter where you look. Full kitchen & bathroom. Local stores and restaurants too. Everyone falls in love with it.

Popular amenities for Southside vacation rentals

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