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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Top guest favorite
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, 444 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 favorite
The exterior of a single-story house is shown, featuring a large deck and a clear pathway leading to the entrance. Nearby, a vintage Coca-Cola sign adds a nostalgic touch against a rustic wooden structure. Lush greenery surrounds the property, providing a tranquil setting.
Cottage in Ashland City
4.92 out of 5 average rating, 116 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 favorite
Treehouse in Pegram
4.91 out of 5 average rating, 350 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 favorite
The exterior of a quaint tiny house is shown against a vibrant sunset sky, featuring shades of pink and purple. The structure includes a covered porch and a grassy area in front, with trees providing a natural backdrop.
Home in Southside
4.99 out of 5 average rating, 127 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 wooden deck showcases a round stone table surrounded by decorative metal chairs. An umbrella provides shade over the dining area, while French doors lead into the cabin. Lush greenery frames the outdoor space, creating a peaceful setting.
Cabin in Chapmansboro
4.96 out of 5 average rating, 418 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 favorite
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, 415 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 favorite
Cabin in McEwen
5 out of 5 average rating, 130 reviews

Quiet Cabin Retreat w/Deer & Cozy Comfort

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 favorite
Treehouse in Greenbrier
4.98 out of 5 average rating, 325 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.

Top guest favorite
Two painted horses trot across a grassy field as the sun sets in the background, casting warm hues of orange and pink in the sky. Lush trees border the scene, enhancing a sense of tranquility in the natural landscape.
Cabin in Russellville
5 out of 5 average rating, 200 reviews

Keehn Hideaway-Hot tub/King bed/Horses/Secluded!

Come relax in our brand new Amish-made mini-HIDEAWAY! (Couples, friends, mother/daughter, business, or ME-time). We built our DREAM PLACE (with a brand new hot tub, GAS grill, and GAS firepit), and we are now sharing it with you! Located on 20 acres in the beautiful hills of Kentucky, you will be AMAZED at the sunsets and quietness. There are no near neighbors except the chirping birds and our horses to pet, watch, and feed. Come be refreshed!

Guest favorite
Apartment in 12 South
4.92 out of 5 average rating, 416 reviews

#1 Hotel in Nashville • 12 South + Rooftop Lounge

Welcome to The Gilmore by AvantStay — Nashville's #1-ranked hotel on TripAdvisor out of 235 properties. This Deluxe King Studio pairs boutique design with full-apartment comforts in the heart of 12 South, steps from the city's best cafés, boutiques, and restaurants. 🛏️ Plush king bed, spa robes & Nespresso 🍳 Full kitchen with full-size fridge 🔥 Rooftop terrace + courtyard fire pit access

Top guest favorite
Home in Clarksville
4.96 out of 5 average rating, 139 reviews

Beautiful & Airy Retreat with Lots of Character

Welcome to your spacious and airy retreat at Russet Ridge! Nestled in a prime location just minutes from Wilma Rudolph Boulevard, this charming three-bedroom, two-bath home offers the perfect blend of comfort, convenience, and style. Whether you’re in town for a relaxing getaway, a business trip, or just exploring the area, this home provides the ideal setting for any stay.

Top guest favorite
The modern kitchen features stainless steel appliances, including a refrigerator and oven, set against a backdrop of tiled walls. A round dining table with black chairs contrasts with warm wooden flooring. Overhead, industrial-style lighting hangs from a high beamed ceiling.
Loft in Ashland City
4.91 out of 5 average rating, 628 reviews

Studio Apartment at The Merchantile

Come stay at this New York style studio apartment located in the heart of downtown Ashland City in the historic Merchantile Building, recently renovated and ready for guests, fully furnished and w/in walking distance of shopping, parks & restaurants and only 20 minutes from downtown Nashville. Check in begins at 3pm and check out is 11am

Popular amenities for Southside vacation rentals

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