Holiday rentals in Southside

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Top-rated holiday rentals in Southside

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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 home in Pegram
4.98 out of 5 average rating, 431 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, 110 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
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, 339 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
Cabin in Dover
4.98 out of 5 average rating, 258 reviews

Cabin on Scenic Farm

Hunt House Cabin: Dogwood Springs Farm & Cabins. If you are visiting Stewart County, this 3-bedroom barndominium is immaculate and truly affordable. It sets on top of one the highest peaks in county with a spring-fed pond at the bottom of the hill with hiking trails. Enjoy the fireplace, fire pit & spacious patio. No cameras. Relax & watch the horses! Boat parking is available. Only 2 miles to boat dock. 1-mile to Cross Creeks. We’ve added a scavenger hunt to make the experience adventurous.

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, 119 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 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, 101 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 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, 398 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, 401 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 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, 209 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.

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, 315 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 favourite
Home in Ashland City
4.96 out of 5 average rating, 157 reviews

Waterfront w/ Kayaks, Fire Pit & Huge Game Room

Enjoy a private waterfront retreat with an elevator, kayaks, a huge game room, fire-pit, evenings by the water, and plenty of room for families, boats, and relaxing getaways just 31 miles from Nashville. Perfect for families, outdoor lovers. Enjoy a well-stocked kitchen, two bedrooms, two full bathrooms. A peaceful waterfront setting that feels far from crowds. This home is best suited for guests looking for a quiet, relaxing stay. It is not a party house.

Top guest favourite
A modern A-Frame cabin, featuring a striking black exterior with a vibrant red door, is surrounded by lush greenery. A wooden balcony extends from the upper level, providing scenic views of the wooded hillside.
Home in Ashland City
4.97 out of 5 average rating, 367 reviews

Lay Away Cabin

Welcome to Lay Away Cabin! Lay Away is a modern A-Frame cabin situated on a wooded hillside, 25 miles from downtown Nashville. Lay Away is a place for couples or small groups to get away, clear the mind, & relax. Close to many outdoor activities , the town of Ashland City & all that is Nashville! This unique cabin offers 4 acres of woods, a hot tub and easy access to the city of Nashville.

Popular amenities for Southside holiday rentals

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