Vacation rentals in Southside

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Top-rated vacation rentals in Southside

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Guest favorite

Loft in Clarksville

4.98 out of 5 average rating, 143 reviews

Spacious downtown loft + 1 parking pass!

"Loft 1881" is a spacious, updated oasis nestled within the walls of this historic 1881 gem. As you step inside, you will be treated to sprawling views of modern amenities paired with the meticulously-preserved industrial charm of the original brick & wood structure. Whether you plan to spend your stay unwinding and watching movies on the projector, or exploring the local restaurants and coffee shops–we’ve got you covered! "Loft 1881" is truly an experience you’ll want to relive time and again.

Aug 8 – 15

G$23,861 GYD per night

Superhost

Loft in Trenton

4.91 out of 5 average rating, 251 reviews

Trenton Industrial Studio

Down a winding country road only 10 minutes from Interstate 24 is a clean newly renovated studio suite in a historic building. The quaint little town of Trenton, Ky a perfect get away town gives a suite with a modern industrial feel and a view of the historic town. It is located above the Traveler’s Lantern Market & Cafe, a full scale coffee and sandwich cafe with handmade farmhouse decor. Trenton also has a boutique, salon, sewing shops and antique store. And a beautiful full park to stroll in!

Sep 6 – 13

G$16,838 GYD per night

Guest favorite

Treehouse in Pegram

4.92 out of 5 average rating, 194 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.

Mar 21 – 28

G$26,543 GYD per night

Guest favorite

Home in Clarksville

4.96 out of 5 average rating, 157 reviews

The PINK HOUSE Clarksville

The Pink House Clarksville is located in downtown Clarksville, close to downtown restaurants, APSU, and 20 minutes to Fort Campbell area. It's a beautiful renovation that includes full kitchen with the most adorable vintage appliances, relaxing seating areas, comfortable top of the line beds, sunroom to sip your coffee in, and even a kids size matching playhouse! 3 Bedroom that sleeps six, home includes laundry room amenity. Be sure to bring your best camera for all the photo opportunities!

Dec 27 – Jan 3

G$36,241 GYD per night

Guest favorite

Home in Clarksville

4.91 out of 5 average rating, 227 reviews

Fort Campbell Retreat w/ Tesla Charger

3 bedrooms and 1.5 bathrooms. Master has king size bed, walk-in closet and own half bath. Spare room has double bed and walk-in closet. Minutes from Fort Campbell, Downtown Clarksville and Governor's Square Mall. 45 Min from Nashville Airport. Neighborhood Walmart Marketplace within walking distance. Brand new washer, dryer and refrigerator. High-speed Wi-Fi, big screen TVs w/ Roku and Nespresso coffee. Relaxing patio deck backing up to a woodland paradise! 50amp Tesla Wall Charger.

Aug 6 – 13

G$18,235 GYD per night

Guest favorite

Cabin in Chapmansboro

4.95 out of 5 average rating, 144 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.

Dec 14 – 21

G$22,823 GYD per night

Guest favorite

Cabin in Dover

4.97 out of 5 average rating, 188 reviews

Cabin & Outdoor Fireplace -Pet Friendly

Hunt House Cabin: Dogwood Springs Farm & Cabins. If you are visiting Stewart County to hunt, fish, kayak, relax, work or visiting family, this property is for you! This quiet cabin is located on our farm that adjoins one of our large barns. This barndominium is immaculate and truly affordable. It sets on top of one the highest peaks in Stewart County with a spring-fed pond at the bottom of the hill with hiking trails. Enjoy the fire pit and the BBQ grille and spacious patio.

Jul 26 – Aug 2

G$20,341 GYD per night

Guest favorite

Guesthouse in Dickson

4.97 out of 5 average rating, 106 reviews

Piney River Farmhouse

Welcome to our guest house, located on the Piney River in Dickson County. This private, gated home is located only a few miles off of I-40, 10 minutes from downtown Dickson, and 45 minutes from downtown Nashville. This private space is above the garage and features 650 sq ft of livable space, an office area with wifi, as well as a refrigerator, Keurig, microwave, toaster, and a TV with plenty of cable channels (plus a fire stick for streaming).

Nov 11 – 18

G$25,007 GYD per night

Guest favorite

Farm stay in Bon Aqua

4.97 out of 5 average rating, 104 reviews

Amazing setting in the country!

Picturesque setting in Bon Aqua, TN. Watch the cattle, horses, chickens and Randy the pig peacefully roam as you drink your coffee. Take it easy at this unique and tranquil getaway, enjoy the farm life as well as a quiet setting while being a short drive to Nashville, Franklin, Dickson and more. There is room for your horses as well if that is a need. Less than 15 mins from 1-40 and an easy drive and plenty of parking for a larger rig.

Aug 28 – Sep 4

G$24,567 GYD per night

Guest favorite

Guesthouse in Ashland City

4.9 out of 5 average rating, 107 reviews

Charming Music City Tiny House

This charming, adorable tiny house sits on a 2 acre property behind our historic log cabin just outside of Nashville, TN. After a full day of exploring music city, guests can enjoy a relaxing and peaceful country evening under the stars away from the city noise. Perfect for a solo artistic retreat or a great getaway with your favorite person! Ryan and I live on site in the main cabin and are happy to help with anything you need.

May 19 – 26

G$17,974 GYD per night

Guest favorite

Barn in Clarksville

4.88 out of 5 average rating, 233 reviews

Barn on farm w/ Hot Tub, 45 minutes to Nashville

This a very unique & personalized romantic stay you won't find anywhere in Clarksville! Our Tiny BARN offers a romantic vibe with a private patio. The patio space is relaxing with a Hot Tub!! We have chickens, cows, a sweet pot belly pig, etc. We also grow. Only a half mile to some of our areas best local BBQ at Red Top. If you like Whiskey start at MB Rolland and try the Pink Lemonade then pop on over to Beachhaven 🍷 Winery.

Aug 20 – 27

G$22,716 GYD per night

Guest favorite

Guesthouse in Clarksville

4.97 out of 5 average rating, 270 reviews

Downtown Guest House With Summer Pool Access

Located in Clarksville's downtown historical district. Stay in a charming 100 year old structure. You will have this little guest house all to yourself. During the SUMMER (Memorial to Labor Day) season, you will have access to the pool. Located within walking distance to Austin Peay State University and downtown shopping/eating. We are about one hour from Nashville and 15 minutes from Fort Campbell.

Mar 18 – 25

G$13,457 GYD per night