Holiday rentals in Southside

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

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.

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 1% w/ King Bed! Cozy&Luxury Downtown Townhome

"Sunjoo's Place on Cigar Hill," Hosted by Byers & Harvey is a 2 BR/2.5 BA with a big bonus room in downtown! The MB has a king bed and ensuite with double vanity and tile shower. 2nd room has a queen bed and ensuite. Downstairs, you can find designated office/perfect kids hang out bonus room with big desk and trundle bed with 2 twin size mattress. However, there is NO bathroom and NO window in the basement. Up to 6 people (max 4 adults) can stay comfortably. Inquire about long-term stays!

Bridge House over Blue Springs Creek

Beautiful in fall, magical in winter! Soothe your soul with an unforgettable escape, surrounded by nature and suspended twenty feet above a babbling brook! Listen to the rushing water and 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.

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!

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.

Serene private new construction walk out apartment

Beautiful 1 bed 1 bath apartment tucked into the woods in Cumberland Heights. Enjoy a private getaway but still convenient access to all that Clarksville has to offer. Close to Austin Peay State University, 10 minutes from downtown and 30 minutes from Fort Campbell. The Space: Comfortable queen bed with full bath (shower only-no tub). Private entrance to walkout basement apartment. No access to main house from apartment. Full kitchen with coffee provided.

The Treehouse Cabin

Beautiful, secluded property 20 minutes from downtown Nashville. Feels like a treehouse! Guests have access to entire property. The apartment has a kitchen, bed, bathroom, and fireplace. There is a large living room with a sitting area, pub table, big screened TV, and couches. To top it all off, guests have a screened-in gazebo with a gas fire pit. You can not beat the serenity or the views! Only 5 minutes to local stores & restaurants.

Find your tranquility at Deer Ridge Cabin.

During our travels, we’ve stayed in countless hotels, motels, cabins, and even tents. It is our opinion that this guest cabin is by far the most well appointed, cozy and peaceful place to rest one’s travel weary body or take a break from the hustle and bustle. These are the things we look for in a memorable stay. We sincerely hope you do as well. Please enjoy your stay at the Deer Ridge Cabin.

Great for the whole family!

Kick back and relax in this calm, stylish space. With 2 living rooms & an outdoor living area, there will be plenty of space for you to spread out and get comfy. New 65" Smart TV & long comfy couch - perfect for movie nights with the whole group! Local Attractions- 5 miles from Downtown Clarksville (~10min) 15 miles from Fort Campbell (~30min) 45 miles from Downtown Nashville (~45min)

Writing and Spiritual Retreat Cabin

A private cabin for people that need quiet, nature, and beauty for inspiration or just rest. Named after Dorothy Day in honor of the social activist, it is intended to provide comfort for body, mind, and spirit. Pet Policy: Unless a registered service animal, we regret we cannot extend hospitality to pets. Please note, pricing is per person.