Holiday rentals in Southside

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Top-rated holiday 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 home in Pegram
4.98 out of 5 average rating, 429 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
4.93 out of 5 average rating, 108 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
4.9 out of 5 average rating, 335 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.

Guest favourite
The interior of the cottage features a cozy sleeping area with a spacious bed dressed in soft linens. Wooden walls provide warmth, while rustic decor enhances the vintage charm. A kitchenette is visible in the background, and natural light enters through the windows.
Cottage in Nashville
4.95 out of 5 average rating, 858 reviews

Recharge and Renew in a Preserved Historic Cottage

Breathe healthy in this hypoallergenic environment. Stay warm around a central stone fireplace and soak up the cultural significance of staying in a carefully restored domestic cottage listed on the National Register of Historic Places. Enjoy a soak in the hot tub to relax a little more. This original tiny house has no separate bedrooms. Spa is near the main house-70 feet from the cottage. Swim wear required. It is private for the cottage guests only. We are 7 miles from downtown Nashville.

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, 117 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.
Flat in Clarksville
5 out of 5 average rating, 204 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, 390 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 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
4.96 out of 5 average rating, 278 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).

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, 392 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, 308 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, 390 reviews

Ark

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.

Top guest favourite
A spacious country home is set among lush green trees, with well-maintained grass surrounding the property. The blue sky provides a bright backdrop, while large windows reflect natural light. The inviting entrance features a pathway leading to the house.
Guest suite in Dickson
4.98 out of 5 average rating, 186 reviews

Country Penthouse

Skip the same old hotel experience and escape the Country Penthouse. The Country Penthouse is set in the beautiful Tennessee countryside amongst the trees. Watch as the sunrises over the tree tops from the private deck and the sunset from the private balcony. Hear the sounds of nature and the birds singing. Let time slip away as you relax and unwind. Enjoy the the wide open spaces away from the hustle and bustle of the city.

Popular amenities for Southside holiday rentals

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