Holiday houses 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 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, 106 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.

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, 116 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 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
4.97 out of 5 average rating, 190 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 modern living area features a comfortable gray sofa paired with yellow accent pillows. A large window allows natural light, illuminating the space. A stylish kitchen showcases stainless steel appliances and dark cabinetry, with decorative items arranged on the countertop.
Condo in Clarksville
4.97 out of 5 average rating, 102 reviews

Make Lemonade in luxury w/ king bed & free parking

You will enjoy your future stylish experience at this centrally-located spacious 2 bedroom, 2.5 bath condo located in Sango, TN near I-24 and approximately 40 minutes from Nashville. Welcome to Make Lemonade where you let our hair down, relax, and leave our worries at the front door. You'll experience peace, joy, and sheer bliss at our brand new condo. you'll look forward to your stay and feeling right at home while making lemonade. You message me for military and extended stay discounts.

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
5 out of 5 average rating, 200 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, 383 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 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, 303 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
4.95 out of 5 average rating, 151 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 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, 387 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.

Superhost
Cabin in White Bluff
4.94 out of 5 average rating, 152 reviews

The Lodge at Oak Haven Farms - Outside Nashville

Perfect way to get away & unplug while being nearby. Close enough to Nashville to enjoy everything it has to offer yet total seclusion for peace and quiet in a one of a kind cabin experience on a beautiful wooded property near Montgomery Bell State Park. Loft up top with full-size bed and bunk beds downstairs with wooded views no matter where you look. Full kitchen & bathroom. Local stores and restaurants too. Everyone falls in love with it.

Top Guest favourite
Barn in White Bluff
4.98 out of 5 average rating, 232 reviews

Cozy Rustic Western Retreat: Van Cleve Bunkhouse

Escape winter at The Bunkhouse, where western spirit meets cozy comfort. Warm beside the indoor fireplace with your favorite beverage, or enjoy s’mores by an outdoor fire —we provide the wood. Set on 15 private acres of rolling hills and woods, this adults-only hideaway at a gravel road’s end offers peace, privacy, and renewal just 45 minutes from Nashville. No pets. Registered guests only. Our goal is to exceed your expectations.

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, 185 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