Vacation rentals in Southside

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Top-rated vacation 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
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, 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
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, 34 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, 361 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.
Earth homes in McEwen
4.98 out of 5 average rating, 1,042 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, 208 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 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 out of 5 average rating, 109 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 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, 230 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
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, 437 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 single-story brick home is positioned on a gently sloping lawn, surrounded by greenery. A concrete pathway leads to the front entrance, flanked by small shrubs. Large windows provide ample natural light, contributing to a welcoming appearance from the peaceful neighborhood.
Home in Clarksville
4.98 out of 5 average rating, 117 reviews

Henrietta House: Quiet Comfort with Fenced Yard

Henrietta House is a recently renovated home on a quiet, leafy street in an established neighborhood. Perfect for families or anyone looking for a fun and relaxing getaway, the home has a full kitchen and a fenced back yard. We are a 15 minute drive to APSU and downtown Clarksville; 5 minutes from Exit 11 on I-24, 5 minutes to Publix and Walmart, 30-40 minutes to Ft. Campbell, 45 minutes to downtown Nashville. Driveway or garage parking. Dogs welcome. No added-on cleaning fee.

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, 289 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).

Popular amenities for Southside vacation rentals

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